Profile Complete!

Before we drop you off in your brand spanking new member dashboard, would you like to take the grand tour?

FREE QUIZ!What's your Calm Business Bottleneck?
What’s keeping your business from steady, sustainable growth? Take the quiz to find out—and get tips on how to grow a thriving digital products business without burning out.
Don’t show this again, thanks!

4 Reasons We Switched Back To ConvertKit from Drip

April 5, 2024

As a creator, should you switch to ConvertKit from Mailchimp, Mailerlite, Flodesk, Drip, etc?

There were four key reasons that led us to move back to ConvertKit after using Drip for the past 6 years.

🙋‍♀️🙋‍♂️ Disclosure: Throughout this article we’ll be sharing our ConvertKit affiliate link. If you switch to or sign up for ConvertKit after clicking this link, we get a small commission. We were not paid by or asked by ConvertKit to write this article, and everything we share in this article is our honest experience and authentic opinion.

Here’s a quick history of our email provider journey:

  1. 2013-2015: We started in Mailchimp, as everyone did back in the day! 😂
  2. 2015-2017: We used ConvertKit and it did an okay job 🤷
  3. 2017-2018: We moved to ActiveCampaign which sucked 🙅‍♀️
  4. 2018-2024: We move again to Drip and it was overkill but solid 🪨
  5. February 2024: We switched BACK to ConvertKit

Having used a good handful of email provider platforms, we can tell you with confidence that no email provider is perfect. They all claim to be intuitive, simple, and offer great customer support. Some are better than others and instead of wasting your time going over the limitations and issues we had with other platforms, instead we’re going to share the four things that brought us back to ConvertKit.

We’ve also included a short list of things we think ConvertKit could improve upon to wrap up this article. Again, no platform is perfect 😉.

Reason #1 We Switched Back to ConvertKit: It’s Built for Creators

Out of all the email providers out there, ConvertKit has evolved over time and really nailed what the modern digital creator needs to run their online business with email marketing.

When we were using Drip from 2018-2024 it always felt a bit like we were the round peg in their proverbial square hole 😅. As the years went on, Drip transitioned to focus more on e-commerce features and the product didn’t feel like it matched our business needs anymore. It became harder to see simple metrics at a glance and spin up simple forms quickly.

One of the BIGGEST features that we loved about ConvertKit and were happy to get back is the Landing Page & Form Signups dashboard:

ConvertKit Landing Page & Form Signups Dashboard

This dashboard, with the ability to hover over all the different bar chart sections, shows you at a quick glance what forms (or lead magnets) are actually converting.

If you’re a digital creator, having this Landing Page & Forms dashboard will change the game for you.

You no longer need to track the conversion of your form/lead magnets, and you can also see them listed out in a grid (or list) that shows total views, subscribers converted, and conversion rate:

ConvertKit Form Analytics

Reason #2 Why Switching to ConvertKit was a No-Brainer: Free Migration

We don’t have the biggest email list in the world (12,000+ as of writing this article), but what we did have was years of email marketing clutter 😬.

The longer you spend with an email provider, the more your tags, segments, rules, automations, email templates, etc get jumbled up. Think of it like your closet… the longer you go between cleaning out your closet the more clothes, shoes, bags, etc pile up.

Here’s what our email clutter looked like before switching to ConvertKit:

  • Email Forms: 27
  • Email Rules: 49
  • Email Automation Workflows: 74
  • Tags: 2,300+ 😱
  • Segments: 80
  • Email Templates: 23

Those numbers (maybe besides the Tags 🙊) may not look too daunting, but the thought of trying to migrate and clean that stuff up was paralyzing for us.

That was until… ConvertKit’s FREE migration!

As soon as we created our ConvertKit account, we filled out the migration form. Now, as of writing this article, if you have less than 5,000 subscribers they don’t handle everything for free:

ConvertKit's Free Migration

That may hold you back if you have less than 5,000 subscribers, but honestly, just taking the action to commit to migrating is like grabbing the big plastic bags and stepping into your cluttered closet.

IMPORTANT NOTE: Just because we had 5,000+ subscribers didn’t mean we weren’t going to be doing any work! We had to spend plenty of time getting all our ducks in a row and cleaning up all our forms, tags, sequences, etc — it’s not possible for someone to know the intricacies of your email marketing setup and migrate it without your input.

Once we were assigned a ConvertKit migration specialist, the process was verrrrrry smooth!

All-in, the process took us about three weeks to migrate everything from Drip to ConvertKit. We setup a Notion Doc to organize everything from our side and to give the migration specialist (Hi, Natalie 👋) a helpful document to work from:

Notion Doc for ConvertKit Migration

Note: ConvertKit didn’t provide this Notion doc, we just created it ourselves based on all the different “features” of our email strategy and used it with Natalie. You could easily do this in Google Docs, etc.

How did all our email clutter end up after migrating?

  • Email Forms: 27 11
  • Email Rules: 49 33
  • Email Automation Workflows: 74 20
  • Tags: 2,300+ 122
  • Segments: 80 8
  • Email Templates: 23 9

The best part about reducing all of those things is that our email account and strategy feels way more concise and organized now. We went from an overflowing closet that was about to burst at the seams to a nice, tidy, and refreshing system.

Again, we cannot stress enough how awesome it was to have ConvertKit’s migration done for free. We spent plenty of our own hours, but it easily saved us 40+ hours of work and a ton of headaches and tasks we didn’t want to do.

Reason #3 We Were Pulled Back to ConvertKit: Their Email Builder

For years while using Drip we were writing snippets of HTML and CSS for…. every weekly email we sent 🤣🙈. Sure, Drip had an email builder, but the experience was really lackluster and we always wanted our emails to feel custom, branded, and easy to create.

When we explored moving to ConvertKit, the first thing we did was create a new Broadcast email to see how flexible and intuitive the email builder was. And, friends? The email builder was SOLID. 👏👏

We are big Notion users, so having the “/block” shorthand in the email builder was fantastic. You can quickly add a paragraph, heading, image, etc without having to do multiple clicks.

The other things we loved immediately about the email builder:

  1. How easy it was to add styling (colors, alignment etc)
  2. How flexible the options are for spacing (margin and padding)
  3. How fast you can crop or add a border radius to an image
  4. How quickly you can inject an HTML block
  5. How easy it is to add/remove sections and format an email for easy consumption

ConvertKit Email Builder

When we sent out our first email from our shiny new ConvertKit account, many of our subscribers who knew we had moved to them asked us, “You created these emails with just the ConvertKit email builder??” So, they’re doing something right!

Reason #4 Why We Switched to ConvertKit: The ConvertKit Creator Network

This is, honestly, a game-changer in the email marketing world. ConvertKit actually helps our subscriber base grow with almost ZERO effort on our part.

And when we say grow, we saw a 100% increase in new subscribers from our previous month without using the ConvertKit Creator Network 📈🤩.

We can illustrate the awesomeness of having the Creator network in this 30-day subscriber chart:

ConvertKit Subscriber Growth

We gained 263 new subscribers in a 30-day period. Nearly 50% of those subscribers came from the Creator Network and happened with very little additional effort on our part!

Previously, we were averaging ~130 new subscribers every month. If the Creator Network continues to deliver at 50% over our previous growth rate, that’s an extra 1,500+ new subscribers we’ll accrue in the next year just from the Creator Network alone. We reached out to one friend in the network and added each other as recommended creators. We plan to do more outreach to related creators in our business niche and keep experimenting with this feature.

We do want to add a small caveat about the Creator Network…

While it IS awesome, it is also about who you can get to recommend you, so your results will vary based on who you know. However, you could easily start recommending other ConvertKit creators and building relationships with them to earn their recommendation in the future. This is a new opportunity for engagement and list growth that hasn’t previously been possible in other email platforms.

Small Ways We Think ConvertKit Could Improve

As we mentioned at the beginning of this article, no email platform is perfect and we have a few recommendations for ways ConvertKit could continue to improve the product:

🏷️ Tag Management

  • Probably the biggest area for improvement, if you have more than 20-30 tags, it’s a real pain to comb through them
  • It would be nice to have a better way to search tags, edit it them, import people to them, etc in one organized place that isn’t the Subcribers’ page sidebar

🖼️ Image Management

  • If you’ve uploaded more than 12 images to ConvertKit’s image library, it’s almost unusable 🤣
  • We’d love to see the ability to search images by file names (Drip had this and we used it often)
  • The ability to search by upload date would be a nice to have (last 7 days, 30 days, etc)
  • Being able to create folders to organize images would be cool

These are just a few things we interact with often, so it’s what is most top of mind for us. But, overall, we’ve really enjoyed our experience using ConvertKit so we’re happy to deal with these small nitpicks.

Should You Switch To ConvertKit?

We trust putting our email marketing efforts in the hands of ConvertKit, and if you’re a digital creator, we believe you’ll be very happy if you make the move.

We hope sharing our reasons for switching back to ConvertKit has helped you!

Our 2023 Year-End Review and 2024 Preview

January 10, 2024

Hello, hello friends! As another year comes to a close, we are happy to reflect on the past year and look forward to the next one.

We’ve been writing these reviews publicly for years, and you can read the others here if you like: 2022, 2021, and 2020.

Jason and Caroline Zook

If love you photos, make sure to scroll all the way to the end of this post to see a photo dump of the year!

While 2022 was the year that probably looked the best from the outside looking in (we traveled full-time in Europe 👩🏻‍🦰👨🏻‍🦲🧳🎒✈️🌍), we both agreed that 2023 is probably the happiest year of our entire lives thus far 😱. Let’s talk about why that is…

👍 What Went Well in 2023

🤔 Why was 2023 our happiest year ever?

Happiness is obviously very subjective, and it’s a bit of a moving target throughout our lives. 20 years ago me (Hi, it’s Jason 👨🏻‍🦲) would’ve looked at 2023 and thought, “how borrrrrring 😴.”

We really settled into our lives in Portugal (which we’ll talk more about in a moment) and have found a solid stride in our businesses. Plus, the ongoing disruption of a year of full-time travel in 2022 really showed us what makes us the most satisfied and contented on a daily basis. Combine that with a home we absolutely adore, a friendly neighborhood, and gorgeous year-round weather, and you end up with a wonderful year.

Now, did we run into challenges here and there? Of course. But, overall, 2023 was a 10/10 year and while not a ton of new adventures were had, we just felt so happy together.

Happy Zooks

Enjoying great food in Portugal

Pool season in Portugal

🇵🇹 We adore Portugal and it has exceeded our expectations

One of the things we mentioned as a preview in last year’s review was acclimating to life in a new country. We feel so fortunate that we found the small coastal town of Lourinhã and that we ended up in a tight-knit community that offers us just enough social interaction.

If you’ve ever moved to a new city, state, or country, you know how hard it can be to make friends. Well, we were shocked to find that our social calendar was WAYYY more full in 2023 than it ever has been in our adult lives.

You can hear us talk more about what we loved about our first year in Portugal in our podcast episode about it (listen on Apple, Spotify, or the web).

Life in Portugal

Living the European lifestyle

👩‍🔬 We experimented a bit more this year in business

We absolutely LOVE the predictability Wandering Aimfully has created in our lives, especially when it comes to revenue. But, we’d by lying if we said we missed the excitement of making new products, launching them, and taking our ideas from a discussion in our living room to a purchasable digital thing.

In 2023, we brought three new ideas to life and they all went well for different reasons…

Experiment #1: Behind The Build LIVE 💻

While we were discussing goals for 2023 at the top of the year, we discussed the idea of adding mini-product launches in between WAIM Unlimited launches throughout the year to scratch our creative itch. Instead of diving into the deep end with a mini-product, we created a MICRO-product, something even smaller to touch our toesies into those waters.

Behind The Build LIVE was a 1-day, live-journal via a Notion page, where we shared the entire process of redesigning our website homepage and building a new lead magnet. We sold access to the Notion page via a pay-what-you-want model, but the money wasn’t the priority. While we did make a couple hundred bucks in sales, we had a lot of fun on the day of, sharing hour-by-hour updates, and feeling the momentum of a new project. We’ll talk more about why this experiment dissuaded us from doing any other mini-product launches in the “What we chose not to do” section below.

Working on Behind the Build LIVE

Experiment #2: Calm Business Encyclopedia 🦋

For many years, we’ve had it on our to-do list to create new content to synthesize everything we’ve taught our WAIM Unlimited Members in our monthly coaching sessions. We finally carved out the time to do this and packaged it together in an A-Z “encyclopedia” of content we named our Calm Business Encyclopedia.

Did we put a ton of work on our plate with 26 separate pieces of written and video content? Of course we did! We’re the Zooks, we always bite off more than we can chew 🤣🤣. However, we worked really well together, we created solid processes to get the work done, and knocked out the content creation without too many late nights. We’re super proud of the Calm Business Encyclopedia and know it’s a solid, helpful, and free resource that will assist many online creators.

Calm Business Encyclopedia

Experiment #3: WAIM of Stones (Members-Only Accountability Game) 💎

Unless you’re a WAIM Unlimited Member, you will probably not have heard of this. To start the year I (Jason, again 👨🏻‍🦲) decided I wanted to stop doing the 1:1 Slack accountability system I’d offered to our WAIM Members for years and shift to a group system. It simply became too much of a mental load for me every week to do the 1:1 work at the scale I was doing it. However, we didn’t want to leave our members without some form of weekly accountability since that’s a key benefit of joining WAIM.

Through a few brainstorming sessions, we came up with a “game” in our Slack community that revolved around themed game boards, digital gem stones, and silly weekly updates to keep people engaged. All-in, 215 of our WAIM Members participated over the course of the year, and many folks said it was the best accountability system they’d ever used! We’re bringing it back for 2024 and are excited to have something so impactful for our members that’s also fun for us to host.

The success of this game was a continued testament to our core value of FUN and our attempt to craft meaningful experiences for our customers that are un-boring.

Creating WAIM of Stones Accountability Game

💸 2023 was our highest year of revenue AND we hit our high member goal

Money isn’t everything, but it is worth celebrating your wins, especially when you’ve taken a very slow and steady approach to growth:

  • When we started WAIM in 2018, it was bringing in $0 per month
  • At the end of the first year, we were making $5,000 per month
  • At the end of the second year, $9,000 per month
  • At the end of the third year, $13,000 per month
  • The fourth year, $24,000 per month
  • We are now up to an average of $38,000 per month in 2023!

Wandering Aimfully MRR 2023

We feel so fortunate that we’ve been able to create consistent revenue growth, while also offering a product (un-boring monthly coaching and more) that our members really enjoy and want to share with other people. Our bi-annual launches continue to work and our weekly email newsletter is the lifeblood of our business (we’ve still not used social media since the end of 2021 for WAIM).

As mentioned, we set a high goal of 300 new WAIM Members in 2023 and we surpassed that goal by hitting 310 total new members! HURRAY! 🎉🎉

💖 It was a good year of health and we stayed consistent with exercise

We found it incredibly hard to consistently exercise while constantly packing our bags and moving to a new place every week or so in 2022.

In 2023, becoming stationary again meant that exercise and good habits came so much easier.

We both made time to exercise nearly every day of 2023 and were feeling healthy and happy to end the year (just in time for all those holiday treats 🙊).

Getting back into a good gym routine

🌟 The best purchases we made in 2023

This seemed like a fun section to add, not only to share with you, but to reflect on what we spent money on that brought the most value to our individual lives and also to our work lives.

👩🏻‍🦰 Caroline’s best life purchase: A <200€ stationary exercise bike

👩🏻‍🦰 Caroline’s best biz purchase: subscription

👨🏻‍🦲 Jason’s best life purchase: Hario Switch coffee dripper (aff link)

👨🏻‍🦲 Jason’s best biz purchase: Screen Studio (aff link) and the Arc Browser (free so no purchase necessary, but it was worth mentioning!)

Barista Jason

👎 What Didn’t Go Well in 2023

🤷 We didn’t travel at all in Europe

You would think that living in Europe would have us brimming with excitement to continue to explore. But… we basically hit travel burnout at the end of 2022. We intended to take a few trips throughout the year, but whenever we’d sit down to plan them, we both agreed we just didn’t want to hop on a plane or deal with all the logistics.

Our ONLY trip of the year in 2023 was going back to the U.S. for three weeks in November to visit our families in Florida and friends in Boston. That trip was (thankfully) very uneventful (as our last two trips back to the U.S. have not been great), but even just that one trip felt overwhelming and exhausting.

Spending 3 weeks back in the U.S.

😩 Our WAIM Member Dashboard redesign project took way longer and went over budget

I’m not sure we’ll ever have a custom development project that ends up in the “what went well” category 😆. The reality of building something completely custom is that you always run into hurdles, you have to make sacrifices on your vision, and the project takes 2x the time and costs 2x the money.

We are extremely happy to have a redesigned WAIM Member Dashboard as it’s a much better experience for our members. Our first experience developing the 1.0 version of the dashboard was a bit of a nightmare back in 2018, and we can at least say this 2.0 experience wasn’t as challenging as the first. Plus, we’re incredibly proud of the final product, so I guess it was worth it.

It’s simply a constant reminder that no matter how long you’re in business, if you have to outsource work that you don’t have the skills for (or don’t have the time to do), it’s rarely going to be a perfectly smooth process.

New WAIM Member Dashboard

🫣 We didn’t get to work on Teachery like we planned

In our 2022 year-end review, we wrote the following sentence: “We think 2023 is the year Teachery makes its biggest jump since it was created back in 2013.”

Welp… that didn’t happen… at all. In fact, Teachery’s revenue and customer numbers were on a slight decline (nothing scary or major, but we’re going in the wrong direction!).

Teachery MRR 2023

We did ship a few solid new features for our customers including Themes, Course Hubs, and a heaping handful of small improvements. We also thwarted a few different spam attacks which revealed some important infrastructure improvements we had to spend time and effort on. We also launched a new homepage for the first time and switched our frontend website over to Webflow. That change will help us as we start to implement more marketing and promotion (read: we can now design and create landing pages without needing our developers!).

The big takeaway for Teachery in 2023: You can’t prioritize something LAST and expect for it to make strides. This WILL change in 2024! 🤞🤞


🦵 Jason’s “not so good” knee

There was a 3-week stint in the summer when we got REALLY into padel 🎾. It’s like tennis, but on a smaller court with walls. We got introduced to it at a friend’s birthday party and it was a lot of fun. Right around the same time, some brand new courts were built near us and we played a handful of times.

That was until I woke up after the 3rd time playing in 3 weeks and couldn’t straighten my knee. I was experiencing some pretty bad pain. An MRI revealed that my previously torn ACL (2007) had been re-torn and there was a lot of meniscus damage. The exact words said by the orthopedic doctor upon reviewing my MRI were, “Yeah, this is not a good knee, man.” It seems all those years of playing basketball are finally catching up with me.

I’ll need to get arthroscopic surgery to clean up some “loose bodies” that are causing a good amount of daily pain in my knee. It doesn’t seem worth doing another ACL repair based on how bad the rest of my knee looks. So, my time playing padel 🎾 was pretty short-lived 😭😭.

Jason's bum knee

🙅‍♀️ What we chose not to do in 2023

A new section we’re adding to our year-end review is what we decided NOT to do this year. We’ll go through these things fairly quickly, but they felt worth acknowledging because sometimes it’s the stuff you choose not to do that frees up time for all the stuff you want to be doing!

We opted not to do any mini-product launches 🐜❌

As mentioned when talking about Behind the Build LIVE, that project was our testing ground to see if we wanted to put in the effort and time to do mini-product launches. What it quickly showed us was the juice would not be worth the squeeze. That micro product experiment was the perfect testing ground to show us staying focused and streamlined was the way to go. While we had earmarked $20,000 – $40,000 in additional gross revenue with two mini-products, we decided to leave that potential money on the table.

This is our enough mindset in action. Yes, that money is wonderful and many people would be so thrilled to have it as additional income, but it would have added stress and a lot more work to our plates. We’ve spent years getting our WAIM business to a predictable and CALM place, why would we add so much extra to our plates when our business is making enough money??

We’re still not using social media for business 🤳❌

Namely, this is Instagram, but we also felt the pull to possibly try using TikTok. We decided not to do either, and staying off social media continues to keep our mental health in a great place without showing any signs of decline in our WAIM business.

We didn’t do a Black Friday surprise 🛒❌

When everyone does a Black Friday sale (we used to as well), we were going to flip that idea and do a surprise for our email list giving away one of our products for free. However, as that time crept closer, we were gearing up to travel back to the U.S. and putting more work on our plates would have left us stressed and scattered. Part of running a calm business means having the discipline to NOT pursue all of your ideas. You always have to weight the opportunity against what you’ll have to sacrifice to see it through, and adding stress on top of a pretty over-scheduled season felt like something we’d regret. So, we tabled the idea for now.

With all three of these items, you can see a recurring theme of savings ourselves stress and extra work that didn’t need to be done to reach our goals. While we set a plan at the beginning of 2023 to do all of these things, we’re happy that later-in-the-year-2023 us said NO THANK YOU and pressed pause on all of these ideas!

🔮 2024 Preview (What’s Next?)

😂 We WILL be focusing on Teachery in 2024!

Say it with us, “We think 2023 2024 is the year Teachery makes its biggest jump since it was created back in 2013.” 😂🙌

There is no doubt in our minds, 2024 is the year of Teachery. We know this because we’re doing everything possible in the beginning of 2024 to put Teachery first on our work plates. Here are a few of the things we’re doing:

  • We used to carve out “Teachery time” on Fridays, but that is now being flipped to spend Monday through Thursday really focused on Teachery with WAIM growth now on Fridays*
  • We’re shoring up all our important WAIM tasks in the month of January (email provider change, podcast plans, content calendar, coaching schedule, etc.)
  • Processes and systems are being created to prioritize Teachery in our daily/weekly/monthly/quarterly planning and schedules

*For any WAIM Members reading this, it doesn’t mean we’re going to ignore our Slack channel or spend less time with you in our monthly coaching, it just means we’re using our “growth” energy early in the week towards Teachery. Thankfully WAIM is at a much more stable place and has much more momentum and well-developed processes than Teachery.

Also, when it comes to focusing on Teachery, we’re specifically talking about focusing on marketing, promotion, and revenue/customer growth. The past 10 years of Teachery being a side project have only been focused (with very little time/effort) on the product itself. We’ve never done marketing and promotion for Teachery, that is a huge change for us in 2024!

💌 We’re switching email providers from Drip to ConvertKit

We were early adopters to ConvertKit (aff link), but made the switch to Drip when we hired a consultant to help us set up some really fancy automations and funnels in 2017.

We can’t say anything bad about Drip, but what we realized is that complicated automations and sales funnels are just not for us. The amount of headaches, technical hurdles, and overall complexity was never worth the return on our investment.

What works best for us when it comes to email marketing? Simplicity, valuable content, and consistency. We’re not opposed to email funnels and automations, we’ve just realized it’s not the right fit for us.

We’ll be switching from Drip to ConvertKit in January and are excited to use an email platform that focuses specifically on creators.

It’s no small task to switch. We have loads of email workflows, automation rules, tags, segments, etc to migrate, but we believe the effort will be worth it (read: enjoying using the email platform and having the platform itself help us grow our audience through some of ConvertKit’s built-in growth tools).

🗣️ Continuing to learn Portuguese

Agora falamos um pouquinho de português 🤏😅. Since February 2023, we’ve been doing a weekly Zoom lesson with an absolutely AMAZING Portuguese language teacher. We love her and she makes learning a tough language as fun as it could possibly be.

Our goal for the end of 2024 is to be able to have our weekly lesson entirely spoken in Portuguese. And, we want to continue to not overdo it on the time we spend each week learning, just continue our slow and steady 🐌 pace we’ve been on!

✈️ Maaaaaaybe some travel, but not too much

The jury is still out on traveling in 2024. We have our eyes on a few different trips, and we absolutely want to road trip to a few different areas of Portugal. But, we still don’t have the itch to pack our bags, hop on a plane, and yada yada.

This could change and you could see a few trips in our 2024 year-end review, but only time will tell.

💰 Continuing to chip away at our new enough number goal

Once we hit our original enough number ($33k per month) in 2021, we sat down and reviewed our financial situation. That first number was set in 2018 and as the years went by, a few things changed in our lives.

We mentioned our new enough number in last year’s review (it’s $56k per month) and that includes a focus on putting money aside for our aging parents, a down payment on a home, and savings for growing our family and not feeling a financial crunch when that does happen.

Like our first enough number, we will most likely not hit our new number in 2024. It’s likely that we won’t hit it in 2025 too, and that’s okay. Our second enough number is a lot like a “gravy number” to us. We live a wonderful life with abundance right now, and in many ways we already have more than enough. We take intentional time to acknowledge that on a regular basis, and that’s the power of knowing what your individual enough number is. The additional money we want to make is simply a focused bit of extra to help in an even more financially secure future.

If you have never sat down to define your own enough number, we highly recommend it. We also have a podcast episode all about the ethos of enough if you want to have a listen (Apple, Spotify, or the web).

🖼️ Wrap-Up: Framing 2024

One of the things we like to do each year is pick a word for the year. This word becomes a helpful bit of guidance as the days, weeks, and months fly by. We use this word as a way to come back to our “why” whenever we’re making decisions or in need of a dose of inspiration.

👩🏻‍🦰 Caroline’s word for 2024: Micro-momentum

I want this year to be about focusing on small actions that create momentum. Rather than getting overwhelmed by the big picture, I want to break everything I do down into manageable, tiny parts and focus on accomplishing those things consistently. A weekly art habit, one painting after another. Daily exercise, one day at a time. Teachery growth, one customer at a time. This year is about consistent, small actions for me.

👨🏻‍🦲 Jason’s word for 2024: Revenuns

Yep, my word is a made up word 😂. Revenuns is a mashup for “revenue / fun,” whereby I know I want to focus on growing our revenue for Teachery in 2024 but I also want it to remain fun. I want every revenue growth decision and tactic we choose to be something enjoyable, unique, and un-boring. And, Revenuns goes the other way too: any fun idea we have in 2024 needs to be tied somehow to revenue growth.

And that’ll do it! We hope you’ve enjoyed reading our year-end review and if you write a review of your own, feel free to use this format and share it with us.

We’d love to read how your year went and what you’re looking forward to in 2024!

And now, our 2023 photo dump…

We became official Portugal residents

Making our rental house more our home

Local Cafe in Caldas da Rainha

Long lunch with friends Maria and Rui

Jason's sourdough baking journey

Jason's 41st birthday

Wonderful nearby hike

Jason enjoying cinnamon rolls and coffee

Taking Caroline's Mom to the Douro Valley

New plant babies

Staying in Ericeira at You and the Sea Hotel

One of our favorite restaurants Holy

Playing Scrabble in Portuguese

Random thrifting and vintage stores

An amazing 2023 in Portugal

Our 2022 Year-End Review and 2023 Preview

January 7, 2023

It’s another year-end review, friends! We’ve been writing these reviews for quite a few years now and we really enjoy cataloging our lives in these annual recaps.

2022 was definitely a year for the record books for us! Many of you already know we spent (almost) the entire year traveling throughout Europe and then we gulp decided to MOVE to Europe! Yeah, safe to say, it was a big one.

Zooks in Switzerland

We’re going to eventually write a full article sharing an in-depth recap from our year of full-time travel, but for now, if you want to catch up on our two-part podcast series recapping that adventure, you can listen below (or watch our travel YouTube videos here):

And now, let’s continue with the year-end review format, sharing what went well, what didn’t go well, what we’re looking forward to in 2023, as well as our guiding words for 2023.

😍 What Went Well In 2022? 😍

We traveled full-time in Europe for the whole year (well, almost)—and it was equal parts amazing and difficult

As already mentioned, a FULL article will be coming that shares a ton more details, stories, and photos from our 300 days living out of suitcases in Europe. For now, here’s the high level summation:

  • 🌍 We visited 10 countries: Portugal, Ireland, Croatia, France, Greece, The Netherlands, Scotland, England, Italy, and finally Switzerland
  • 🏙️ We stayed in 30 different cities (England had the most at 7 and The Netherlands had the least at just 1)
  • ✈️ We took 17 flights across Europe (no lost luggage or canceled flights if you can believe it!)
  • 🚂 We rode on 5 trains
  • 🚕 We drove 8 rental cars (half of which were on the opposite side of the road from what we’ve known our entire lives)
  • ⛴️ We took 2 ferries (technically, the same ferry… round trip)
  • 🏨 We stayed at 31 Airbnbs and 15 hotels
  • 🛌 We slept in 50 (!!!) different beds
  • ⭐️ We ate at 12 Michelin Star restaurants (major bucket list item for Jason!)
Jason and Caroline Zook Full Time Travel 2022

Everyone would probably plan a year of travel differently, but we have to say there’s not a ton we’d change about our itinerary.

Before we embarked on our trip, we set the intention of traveling slightly slower than most folks you see on YouTube. We planned to avoid bigger, more popular cities, and we knew changing locations every 3-4 days was NOT a recipe for success for us. 2 weeks was more what we were aiming for in a place. We did a pretty great job of sticking to our initial plans!

With all the amazingness that this year of travel brought, it was also really hard on us at times, especially on Caroline. That being said, even starting the year with pretty severe flight AND driving anxiety, she pushed through (on her terms) and developed a lot more resilience as the year went by.

Zooks in Dublin, Ireland

Zooks renting a car in France

Zooks roadtripping through the UK

Zooks flying RyanAir

Zooks dealing with driving anxiety in Europe

One of the hardest parts of the trip that is also one of the hardest to explain to someone not traveling full-time was the never-ending decision fatigue. Things like what grocery store to go to, what to eat for lunch, how customary things like parking and garbage work, and so many other “simple” life things that get complicated as you arrive in a new city where people speak a different language and you have no idea where anything is. That, coupled with the endless decisions of what we wanted to see, where we wanted to go next, where we wanted to stay, it was just… A LOT. We’re not complaining by any means, we gladly take on that decision fatigue for an experience like this we’re so grateful for—we just feel sharing the reality of the full-time travel life is as important as the glamorous parts.

We could write SOOOOOO much more about our year of travel and we will! But for now, just know that overall this was definitely a huge positive for us in 2022, and it was life-changing in many ways.

Zooks in Lisbon, Portugal

Zooks at James Fort in Kinsale, Ireland

Zooks standing at the highest point in Hvar, Croatia

Jason Zook solo sightseeing in Paris, France

Zooks in La Capelle, France

Zooks at Royal Senses Resort in Crete, Greece

Caroline Zook with Scottish Highland Cattle

Zooks at Dunnottar Castle in Scotland

Zooks at a wedding in Puglia, Italy

Zooks at Lake Lungern, Switzerland

🤳 We (unintentionally) took a year off social media, and don’t plan to go back anytime soon

Traveling full-time for a year… what great content to share on Instagram and TikTok, right!? Well… that may be true, but over the years we’ve learned: just because something is a “good” opportunity doesn’t mean it’s the right opportunity for you. We ended 2021 on a short break from IG (for our business account @wanderingaimfully), which eventually turned into not returning for all of 2022. I shared exactly FOUR posts (and two stories) on my personal IG account before realizing I simply didn’t care and didn’t want to spend the effort, and Caroline dipped out at the end of January for her own mental health.

As the months went on, we would have these amazing moments and think out loud, “gosh, this is pretty Instagrammable,” only to then come back to asking ourselves, “but why post it? 🤷🤷🤷”  We know that some people love using Instagram (and TikTok) for promoting and marketing their businesses by sharing their lives, which we are 100% in support of if that’s what’s right for you. But for us, we finally reached a point where the negatives just outweighed the positives. We’ve prioritized building a business over the course of now five years that can survive without participating in the daily content grind, and we’re so so glad we made that decision because now we can choose when and how we show up in those spaces.

What we realized toward the mid-way point of 2022 was that if we’re not going to share the MOST “sharable” year of our lives on social media, that’s probably a sign we’re done using social media altogether. We’ll see how that position evolves—never say never—but for now, 2023 will likely be socials-free for us.

🏊‍♀️ Our businesses stayed afloat and we’ve built great systems and processes

Before we sold the last of our things and moved out of our rental home in Southern California, we had many conversations about what our businesses would look like in 2022. For those of you that don’t know, we run two businesses together: 1️⃣ Wandering Aimfully Unlimited (WAIM), an un-boring coaching program and 2️⃣ Teachery, a small online course software platform.

Both of these businesses give us the freedom and flexibility to work on them from anywhere, but they both do require our ongoing input and time. We were happy to discover that we absolutely COULD keep both businesses up and running, and even though we had virtually zero extra time to do more than the bare minimum tasks, our top-line revenue only decreased by 5% from 2021. Considering 2021 was our best year yet, and considering our time input in 2022 was a fraction of what it was in 2021, we feel like that’s a pretty amazing feat to accomplish! It’s also a reminder that you’ll never know whether you can work less hours, create less content & marketing, and still thrive until you really put your systems and processes to the test and check your own assumptions.

Wandering Aimfully MRR 2018 - 2022

We are truly grateful that we’ve honed our systems and processes over the years, especially as 👩🏻‍🦰 has become a Notion Wizard 🧙‍♀️. Notion (aff link) is truly a game-changer for us and keeps everything organized and on-track (even when we were completely exhausted after a long travel day from one country to another). We never lost sight of what we needed to do to keep the wheels on, and that was invaluable.

Zooks podcasting in Europe

Zooks co-working in Preston, England

Zooks being digital nomads in Agia Pelagia, Greece

Hiring freelancers for accessibility and design

If you would have asked us, “Hey Zooks, do you plan on bringing on any freelancers in 2022 while traveling full-time?” the answer would’ve been a resounding: NOPE.

However, we actually brought on TWO new amazing humans to help our businesses!

🙌 Accessibility (Captions, Transcripts, etc)

It’s been a goal of ours to make our content (videos, podcasts, coaching sessions, etc) more accessible for a wider range of people who need/prefer different ways of consuming information. We were happy to find someone who LOVES the process of transcription, and is very good at it!

Notion hub for accessibility tasks

👩‍🎨 UX/UI Designer (for Teachery)

If you didn’t know, Caroline did the entire branding and application redesign of Teachery back in 2020… BY HERSELF 😱 (and she’s not a UX/UI designer). With a long list of features we wanted to add to Teachery, we simply knew Caroline wouldn’t have the bandwidth to continue to do design work for our online course platform. We stumbled into finding a designer who had some availability pop up, and we’ve been working together for 4 months with great success. It’s a wonderful feeling to have someone else bringing our ideas for Teachery to life, and then making them even better by adding their unique skillset.

Figma design file for Teachery

We created one new product for WAIM in 2022: the Teachery Theme Pack [includes a new Teachery feature: Themes]

This one we count as a two-fer because it involved a really big new feature for Teachery: Themes. You can read more about Themes here if you like, but this is a feature that helps our creators take their pre-designed courses and sell them as copyable designs for anyone to use and create new courses from.

On top of that new feature for Teachery users, we also wanted to give our WAIM members a handful of pre-designed Themes by us. We sat down and brainstormed 5 different Themes that we thought our core group of members would find useful. The Themes we ended up on were:

  1. 🧘 Monochrome Yoga Theme (a minimal, monochrome color palette design for yoga instructors and wellness professionals)
  2. 📝 Pastel Planners Theme (a playful, pastel color palette design for digital planner creators and artists)
  3. ✨ Bold Design Theme (a striking, quirky color palette design for designers or developers)
  4. 🌚 Dark Photography Theme (a simple dark mode color palette for photographers or filmmakers)
  5. 🌝 Light Novelist Theme (a simple light mode color palette for writers and copywriters)

(And any of these Themes can be adapted to ANY type of online course, with instructions on how to customize the images, color palettes and fonts. Pretty cool!)

As is with all new products we create, of course it took more time than we wanted, and we went a little bit over and above in the execution 🤷‍♀️🤷. But, we’re always happy to invest in delivering awesomeness to our WAIMers, as we truly appreciate them and want them to be happy they invested in us!

Teachery Theme Pack

🏠 Finding our new home in… Portugal! 🇵🇹

Moving away from work stuff, this is a pretty big one 😂😂😂. We moved to Portugal!!! Sayyyy what!??

After visiting Portugal (Lisbon, specifically) in January, we really fell in love with Portugal. And, if you can fall in love with a country by only visiting one city, then you know it has a lot to offer. We planned a return trip in August to scout out two separate areas where we might actually want to live (big cities are not exactly our jam and Lisbon is definitely a big city to us). What happened on that scouting trip is that we absolutely fell in love with a small town in the Silver Coast (just 45min north of Lisbon) and found a dream home to rent for a year 😍❤️.

Zooks deciding to move to Portugal

Zooks in their new home in Silver Coast, Portugal

Zooks putting together IKEA standing desks

Jason Zook baking cinnamon rolls in Portugal

Zooks enjoying Portugal sunsets

Zooks enjoying Douro Valley wine in Portugal

If you want to listen to our podcast episode where we made the decision, it’s embedded here for ya:

We also recorded this podcast episode and this episode where we share what the first few weeks were like living in a new country.

Right now, the plan is to stay here for a few years and even possibly earn dual citizenship in the EU (which takes 5 years). We’re not making any crazy long-term plans at the moment, but we are SUPER happy so far and can’t wait to explore so much more of Portugal, as well as learn the language.

😔 What Didn’t Go Well In 2022? 😔

We both got COVID-19 and Caroline got shingles for a 4th time

Covid has been hard on everyone and it was particularly difficult for our families last year. That being said, we had successfully dodged it until we hit the road… during the Omicron variant 😬.

I (Jason) picked up the virus toward the tail-end of our FIRST week in Lisbon. Woof. Thankfully, I’d just gotten my booster shot right before we left, and I do believe that was helpful in keeping my symptoms mild. Caroline actually didn’t even catch it from me, which is hard to believe given how small our flat was, BUT perhaps it has something to do with my amazing “COVID fort” (see below)? Luckily, if I was going to get it anywhere, it was good to be in a city that was so easy to get access to testing, food/grocery delivery, and helpful people who could pass along the most up-to-date information. We did have to cancel our second planned stop of our trip to San Sebastián, Spain, but we didn’t mind the extra time in Lisbon as we were just loving Portugal.

Jason Zook building a covid fort in Lisbon, Portugal

Caroline picked up the virus in the third country on our trip: Croatia. Unfortunately, COVID was a bit harder on her than it was on me, but again we had very friendly people to pass along helpful information and a comfortable Airbnb to “nest” in while her body fought it off.

Caroline Zook in her covid nest in Split, Croatia

Having dealt with both us getting covid, one of Caroline’s additional points of anxiety during 2022 was having a shingles flare-up again. We know by now that this is just a recurring response Caroline’s body has to emotional stress. In 2021, we dealt with some pretty difficult family situations and Caroline had TWO shingles flare-ups as a result, so we know the cause and effect well by now. Our packed travel schedule that ramped up in April, plus the emotions of adjusting to full-time travel life and maybe even a fatigued immune system led to shingles rearing it’s ugly head for a FOURTH time while we were staying at a “tiny chateau” in France (it wasn’t actually a chateau, we just liked to call it that for fun).

This was one of those situations where we were in one of the trickiest locations to get sick. We were staying in a TEEEEEENY tiny town and the nearest place with a pharmacy or doctor was a 30+ minute drive. We ended up going to a pharmacy where we found a woman who spoke a tiny bit of English, found us a doctor who was “Canadian,” and we were able to book an appointment fairly quickly. The hilarity that ensued is that the “Canadian” doctor (reminder: we’re in France) was FRENCH Canadian 🤣🤣. He spoke even less English than the nice French pharmacist. But, all language barriers aside, we were able to secure a much-needed prescription of shingles anti-viral meds and pick them up for a total cost of €56 (€25 for the doctor’s visit and €31 for the pills).

Caroline Zook using Google Translate in a pharmacy in France

Caroline Zook meeting with a French doctor in Uzes, France

The meds ended up doing their job and, thankfully, Caroline avoided the dreaded shingles rash — which is the absolute worst thing. But, the meds had some gnarly side effects for her and this would end up being the lowest point of our entire trip. I half-expected Caroline to ask to go back to the U.S., but to my surprise she didn’t want to cancel our trip, she just wanted to get the heck out of France 😆 (France was honestly absolutely lovely though, with food that lived up to the hype and patient, kind people—we look forward to going back under different circumstances!)

📉 Our WAIM website traffic and email subscribers continued to decline (but revenue stayed steady!)

This is a trend that continued from 2020 to 2021 when we wrote last year’s review. Our overall website traffic and email subscriber numbers have been on the steady decline. Here’s what those numbers look like for WAIM:

  • 🧑‍💻 2020 unique website visitors: 353,021
  • 🧑‍💻 2021 unique visitors: 206,574 (⬇️ 41.4% decrease)
  • 🧑‍💻 2022 unique visitors: 121,805 (⬇️ 41% decrease #consistent)
  • 📬 2020 total new email subscribers: 2,845
  • 📬 2021 total new subs: 4,469 (📈 41.4% increase)
  • 📬 2022 total new subs: 2,634 (⬇️ 41% decrease)
  • 💸 2020 total net revenue: $168,102
  • 💸 2021 total net revenue: $274,359 (📈 63.2% increase)
  • 💸 2022 total net revenue: $313,553 (📈 14.2*% increase)

*This 14.2% number is JUST our WAIM net revenue, and the overall revenue number doesn’t include Teachery or other income sources. Total overall revenue in 2022 was 5% less than 2021 🤯 after factoring in everything else!

Now, that’s a TON of numbers to look at, but hopefully, it paints an interesting picture — it certainly does for us!

We’re not overly concerned with the decrease in organic website traffic or in new email subscribers, because our WAIM revenue has actually been increasing year-over-year 🎉. We know by now that you can’t focus on EVERYTHING all the time, so sometimes you have to intentionally de-prioritize things. Our marketing bridge was working well enough that we knew we’d be okay to focus the majority of our energy on our program and our members, and leave our traffic and subscribers goals for another day.

There are several factors that contributed to our WAIM revenue increase, but the main 3 to share are:

  1. We’ve gotten MUCH better at positioning and communicating our offer (WAIM Unlimited)
  2. We’ve found a promotion schedule (bi-annual launches) that works well for us
  3. Our existing WAIMers are helping bring in 60% of new members (affiliates!)

With all that being shared, we will be focusing our efforts on traffic and email subscriber growth in 2023, but we’re certainly not planning on burning ourselves out with concern. We assumed our numbers would stay fairly similar or decline in 2022 due to having less hours to pour into our business(es). Thankfully, as noted above, our total overall revenue across the board was only down by 5% in 2022 which we did a celebratory butt-bump for in Switzerland…

Zooks doing a butt bump in Switzerland

😬 Recording YouTube videos to recap our travel adventures

We decided to put this in the “didn’t go well” section because, as much fun as the completed videos are to look back on, they really are a thorn in our sides to create.

It’s sooooo easy to watch travel YouTubers and think, “I could totally do that!” But then, when you’re traveling AND when you have two businesses to keep afloat, you realize just how much extra time and effort goes into recording, planning, organizing, editing, and publishing YouTube vids. If we didn’t have WAIM + Teachery, creating video content would be wildly easier.

As of writing this year-end update, we still have two straggler remaining travel videos (Italy + Switzerland) to edit and publish. We give travel YouTubers who also run businesses a TON of credit for consistently uploading! The next time you watch one of those videos, make sure to give those folks a 👍 as it’s not easy work.

Oh, and in case you were curious, our YouTube stats for 2022:

  • 16 videos uploaded (vs. 7 in 2021)
  • 1,847 new subscribers (vs. 3,047 in 2021)
  • 234,402 total video views (vs. 199,874 in 2021)
  • $2,947 revenue earned (vs. $3,478.50 in 2021)

In 2021, our first “Packing for Full-Time Travel” video had a huge surge in viewership, eventually hitting 150,000+ views which attributes to nearly all of the 2021 YouTube analytics.

Wandering Aimfully YouTube Channel

😵‍💫 It was a year of amazing memories, but also a year without a lot of breathing room

Capping off this section, we just want to share that while full-time travel life IS a dream come true (and we WOULD recommend it), it’s also very tiring and if you’re juggling work while living out of suitcases and Airbnbs/hotels, you don’t have much space (physical or mental) to breathe.

That said, there’s not a whole lot we’d change about our travels in 2022. Again, we just want to share that traveling for a year can look extremely glamorous and enviable from the outside (and it absolutely is at times!) but on the whole, it’s a lot of effort and (for us) not a sustainable lifestyle long-term.

🔮 2023 Preview (What’s Next?) 🔮

Getting more acclimated to life in Portugal and gaining long-term residency

As of writing this recap to you, two things are currently happening:

1️⃣ We’re sitting in our new home in Portugal and pinching ourselves daily at how happy we are and how unbelievably lucky we feel to have found the area and the home we’re renting.

2️⃣ Our long-stay (D7 Visa) applications have been approved 🎉🎉🎉 and we are awaiting our appointment here in Portugal to receive our official residency card (good for 2 years).

For 2023, we hope to settle deeply back into “normal life” routines. You know, working from the same spot each day, using the same kitchen for each meal (and a batch of cinnamon rolls), sleeping in the same bed, and dealing with only ONE language barrier for the year!

Zooks working at standing desks in Portugal

We also DO want to explore more of Portugal! We envision taking 3-4 road trips in 2023 up to the north of Portugal (Porto area) and the south of Portugal (the popular Algarve). We know a few expats in both areas, so it’ll be fun to connect with those folks when we do hit the road.

Speaking of meeting people, our goal is to try to meet some new friends in Portugal this year. We want to spend quality time learning Portuguese (we know it’s going to take years!) and we want to embrace local customs and cultures as we bump into them. Anyone who has moved to a completely new city knows how hard it can be to make new friends, and we earn an extra level of difficulty being the foreigners here 😄🙃.

But yeah, we’re excited to be in the same place for weeks/months on end too. Full-time travel is not the lifestyle that works best for two Netflix-loving homebodies!

Zooks on their couch in Portugal

🏇 Jumping back in the business saddle and working on growth for WAIM and Teachery

As we noted a few times, things simply stayed afloat with Teachery and WAIM in 2022. Well, technically we did better than just floating, maybe it was a light bit of swimming in 2022 with our businesses.

👥 What does growth look like for WAIM in 2023?

We mentioned the website traffic and email subscriber numbers already, but we are trying to grow WAIM’s revenue in 2023. We’ll talk more about numbers in a moment. We had a total of 216 new WAIMers join us in 2022, and we don’t have a specific number we’re trying to hit in 2023, but if you’re asking us to pick a number: a high goal would be 300 total new WAIMers in 2023 🎯.

Wandering Aimfully member Notion database

⚙️ What does growth look like for Teachery in 2023?

Ahhh Teachery, the side project that could! Teachery has always been a great little SaaS for us and has increased in revenue each year with virtually zero external effort on our part. Teachery doesn’t have a content strategy, we do NO marketing or promotion of it—it only continues to grow because our Teachery customers love it and help spread the word about it 🙏❤️.

That being said, we think 2023 is the year Teachery makes its biggest jump since it was created back in 2013. Feels fitting on Teachery’s 10th birthday to make a leap, right? Now, we’re not talking a gigantic leap, but we’d like to see our annual revenue increase by 50%. That’s a big goal and not sure we’ll hit it, but it’s also the very first time we’ll be putting in any revenue growth effort!

Teachery MRR chart 2014-2022

💰 Chipping away at our new “enough number” that we set at the end of 2021 ($57,000/mo)

In 2021’s year-end review, we shared that our “enough number*” increased from $33,000/month to $57,000/month**. We hope it was VERY clear that our goal wasn’t to immediately make a 73% revenue jump per month. That new monthly goal is the number we’re working toward and at the rate we’re going, it will take a few years to get there (and that’s okay!)

*We talk in detail about defining an “enough number” in this article. 🤗👍

**It’s important to keep in mind this number does not mean we take home $57K. This is a top-line revenue number so it doesn’t account for expenses, paying freelancers, affiliates, taxes, etc.

If you’re asking me to make a prediction about 2023, my hope is that our monthly revenue would creep into the 40s this year. But, we’re not interested in chasing these numbers at all costs. We want to enjoy life, we want to feel good about our workload, and we don’t want to pile on a ton of additional expenses just to boost our monthly revenue number.

🖼️ Let’s Wrap It Up! How Are We Framing 2023? 🖼️

👩🏻‍🦰 Caroline’s word for 2023: Capable

2022 was a big year for me in terms of stepping outside of my comfort zone and really surprising myself with some of the discomfort I was able to move through. The reward for expanding my capacity for discomfort is that my anxiety levels are lower than they’ve ever been. What a gift! I feel like I’ve actually shifted my own self-perception, which, when I type it out like that, feels profound. I want to carry this new self-image into 2023 and show myself just how capable I am. In areas of health, relationships, speaking up for myself, being more assertive, and carrying less responsibility for others as a way to gain favor.

👨🏻‍🦲 Jason’s word for 2023: Invest

Now, you might be thinking, “cool, bro, so you’re buying low and selling high??” NOPE! Well, yes if we can, that’s just smart financial advice, but the word invest for me in 2023 is based on a few different things.

Investing in my health: I turned the ripe old young age of 40 in 2022 and while getting older doesn’t scare me, there are some truths and realities to it. That being said, after a year of not having a ton of time to prioritize health, I’m excited to invest heavily in my health with daily-ish exercise, getting some regular doctor checkups done, updating my eye prescription (maybe getting lasik eye surgery?), and focusing on a more balanced diet. Don’t worry, I believe cinnamon rolls and 🍪s are also investments in health too 😘.

Investing in our relationship: Traveling the world was a dream come true for us, but it also put a strain on our relationship at times. Especially as we’re navigating our new lives in a completely new country (with all kinds of fun logistical hurdles), I really want to focus on more quality time and thoughtfulness in our relationship because we’re in this for the long haul 💖.

Investing in our businesses: 2022 was not a growth year for our businesses (which was expected!), but we’d really like to make some strides in growing our revenue, our traffic, and honing in our processes even more. Investing in our businesses in 2023 should set us up well for many years to come!

Are you writing a “Year-End Review”? We’d love to read it!

If you are, we’d love to read what you’re up to! Feel free to use the format we laid out here as an example and use our contact page to pass your review along to us.

These reviews are so fun to look back on and give us a ton of perspective as time passes along.

Hope you enjoyed reading about our 2022 and all that we have planned for 2023!

How To Grow Your Online Business Monthly Revenue From $0 to $10,000++

October 19, 2022

In this article, we hope to help you learn how to grow your online business monthly revenue from $0 to $10,000++. We are NOT about overnight success or viral tactics, which is why we call this process: Grow It Gradually 🦋.

👋 PLEASE READ: Before you scroll to the $10,000++ section, the idea behind this article is NOT to leap from $0 per month to $10,000++ per month overnight. That’s simply not possible. But, what is possible is to make small revenue jumps over time with your business. Remember, taking the slower 🐌🐢 approach to biz is still a successful way to grow!

What you can look forward to…

We’re going to share 3 tips in each revenue “level” of your business so that you can Grow It Gradually 🦋. The five “levels” we’ve identified and experienced are as follows:

  • $0 → $500
  • $500 → $1,500
  • $1,500 → $3,000
  • $3,000 → $5,000
  • $5,000 → $10,000
  • $10,000 → $10,000++

We want to make it EXTREMELY CLEAR that regardless of how much money your business makes, you are welcome and celebrated just as you are! There are SO many more important, more interesting measures of success and growth beyond just money.

Making more money doesn’t make you better at business or more important than anyone else.

But alas, in our experience, money can buy FREEDOM and that’s really what we want for you.

We hope, in each section of this article, you walk away with actionable takeaways for whichever level you’re currently at or striving to get to (at the pace is right for YOU!) Now on to the show…


Welcome to our Grow It Gradually 🦋 article where we’ll walk you through how to jump up 5 different revenue levels in online business. And as a final reminder, making more money doesn’t make you better at business or more important than anyone else 🤗.


Grow Your Online Business Revenue from $0 to $500 per month: Start with a Client-Service Business

When we were just getting started with our businesses, one of the biggest issues was trying to figure out what type of business and revenue model to pursue.

Online courses sound great, but if you don’t have an audience, who are you selling them to? The unfortunate answer is: No one 😩😩😩.

Software (aka SaaS) is cool, but if you have zero developer skillz (yes, skillz), it’s going to be a looooooong time before you can start making money.

If you’re trying to grow your online business from scratch, we recommend starting with a service-based business.

Service-based businesses come in many shapes and sizes: Graphic design, web design, web development, virtual assistance, copywriting, art therapy, personal styling, social media management, the list goes on and on.

Essentially, you are a person with a specific skill, getting paid for the hours you work for someone else’s business.

This is a GREAT business model to start with because you don’t have to have a big audience or a social media following; all you need is to have cultivated a specific skill that you can monetize. With just a few clients in the door, you’re likely making enough money for a healthy side business (rather than a products-based business which would take significantly more sales and effort to make the same amount of money.)

💡 For the rest of Grow It Gradually 🦋, we’re going to use a fictitious business example so you can put yourself in the shoes of a fledgling biz and watch it grow. Let’s call our business… Oodles of Poodles Web Design 🐩🎨. Here at Oodles of Poodles, we specialize in helping people launch elegant websites on Squarespace. We focus on designing and building websites for small business owners in the health and wellness space. (Are we health and wellness experts? No! But we know there are many new businesses popping up in that niche and we love a good skincare routine as much as the next person, so we’re going to target them.) Our mascot is Prism, a lovable Poodle who has yet to learn how to build websites, unfortunately, but we’re working on training her! 🐩

Great, the (fictitious) business is established and we know who we can help [health and wellness experts] and with what services [Squarespace website design] we can help them with. Now, let’s get into the three tips in this section for Oodles of Poodles 🐩🎨 to get their business foundation right and their first client(s) in the door.

⚡️ Tip #1 at the $0 – $500 stage: Be VERY clear about what you do and who you do it for (ps. You need a website!)

You may have noticed in the short bio for our fictitious business, we offhandedly threw out there our web design company focuses on helping small business owners in the health and wellness space. THIS. IS. IMPORTANT.

One of the biggest mistakes we made early on that we see new business owners make as well is NOT specifically stating who your business is for.

It may seem limiting to pick a specific group of people that can pay you money, but trust us, if you cast too wide of a net and just say you do “web design for small businesses” you aren’t going to ATTRACT 🧲 anyone. We’re going to go into more detail about this in the next section.

The other part of this first tip is to identify what exactly you do.

For Oodles of Poodles 🐩🎨, hopefully you noticed we wrote “build elegant websites on Squarespace.” We want to focus on the skills we have and the software we know how to use.

We don’t want to learn how to use WordPress, Wix, Weebly, Webflow, or any other website platform that starts with a “W” 😂😂. Plus, this is another way to attract a specific type of customer who uses the platforms you know.

Once you can answer these two questions, the logical first step is to create a website.

This is very important though: Don’t overthink this step! Give yourself a specific deadline of when your website needs to be launched for your biz. Constraints are incredibly important and we’ve all had those “under construction” pages up on our sites for longer than we should’ve.

⚡️ Tip #2: Start BEFORE you’re ready and courageously practice putting yourself out there.

Everyone open your ears… 👂👂… Are they open? Good. You ARE going to have to reach out to people before your business is “perfect.”

You ARE going to have to put yourself out there on a limb that’s a bit uncomfortable. We ALL do this!

To get your first couple of paying clients, you may need to do things like:

  • Post on any social media account you have letting people know you started this new (business) adventure and you’re looking for clients
  • Text message friends and family offering up your services (if you want to do this in a non-spammy way, send along a friendly note with your new website and ask your friends/family to pass it along to anyone who might be in the market for your particular skill)
  • Cold email local (targeted) businesses in your area with a value-packed pitch on how you can help them*
  • Embrace the fact that people will say “No” to you and that’s OKAY (it does NOT mean you are a bad person)

📌 *Related content alert: We recorded a podcast 🎙 episode titled, A foolproof way to get more clients, and it’s worth a listen if you’re at this stage of biz.

It’s really really really important to avoid overthinking everything early on in your business. Oodles of Poodles 🐩🎨 is not going to get its first paying client with hopes, prayers, and crossed fingers. It takes doing outreach and being proactive.

At the $0 stage of business the most important thing is getting SEEN. You have to promote yourself and you have to understand that promotion is NOT a bad thing.

Promoting yourself ≠ being a sleazy salesperson. Those are not the same things. We love this quote from Tina Roth Eisenberg:

Quote by Tina Roth Eisenberg

Head’s up: Be prepared that your friends, family, and acquaintances may criticize you for putting yourself (and Oodles of Poodles 🐩🎨) out there.

We’ve learned that nearly all criticism in business comes from other people’s insecurities and fears. Know this, and put on your invisible suit of armor, ready to ward off any unwanted criticisms of your new biz!

⚡️ Tip #3: Create a buzz-worthy “launch” event.

One thing we don’t see enough new biz owners do is leverage the “new-ness” of their business to create buzz early on.

Now, we understand being quiet is more natural to some people, but businesses need to be seen/heard before they can get paid!

Here’s what we’d do for Oodles of Poodles 🐩🎨 if we were just getting started:

  1. We’d create a simple landing page that has a launch date, countdown, and a call to action to sign up for the email announcement of an exclusive offer
  2. On that landing page, we’d show off a few examples of our Squarespace web design skills, and also have a fun photo or two of Prism, the poodle 🐩 looking awesome (anything that makes your launch more memorable and full of personality is a win!)
  3. We’d come up with some branded social media graphics that promote the 🐩🎨 launch event (more fun photos of Prism, obvs)
  4. For 2-3 weeks, we’d promote the launch event on all our social channels (“Something exciting is happening, join me!”)
  5. We’d write our first email newsletter that would offer three web design client spots at a 50% OFF discounted rate (this is the exclusive part) – This email would also focus on what we do and who we do it for!
  6. We’d focus on the launch event being FUN, exciting, and a new adventure for us and Prism!

Optional: If you’re a much more extroverted person, you could also do some sort of video launch. It could be done on Zoom, YouTube Live, IG Live, etc, and the entire call-to-action of your buzz-worthy event would be to attend that (instead of OR in addition to the email signup).

This type of launch event is not just about getting those first three paying clients. It’s about doing what we talked about in Tip #2: showing people your biz exists!

If you get a paying client, that’s obviously your main goal, but at this stage of the game, just getting people to know you are offering this service is critically important.

If you can work through these three tips, you should absolutely be well on your way to landing your first paying client (or two, or three!)

There’s no specific timetable on how long these things should take, but we’ll remind you of one important thing: You have to get started before you feel 100% ready! No one feels 100% ready at the $0 stage of business.

Next section, we’re on to our next stage and we’ll tell you what to focus on next once you earn hit that first $500/month benchmark. 🦋


⚡️ Tip #1: Be clear about what you do and who you do it for (ps. You need a website!)

⚡️ Tip #2: Start BEFORE you’re ready and courageously practice putting yourself out there.

⚡️ Tip #3: Create a buzz-worthy “launch” event.


From $500 to $1,500 per month: Build Your Business Foundation

Let’s say your business is generating around $500 every month and that’s about 500x better than $0, but you know $500 can’t pay all your bills, so you’re looking to grow. What do you do?

If you missed it in the previous section, we’re going to use our fake business Oodles of Poodles 🐩🎨 Design Studio (a company that does Squarespace website design for health and wellness businesses) as our ongoing example.

⚡️ Tip #1: From your first few customers, can you look for patterns and identify a clear customer profile?

One of the most important ways you can grow your business is to get crystal clear on WHO your target customer is.

Even with our Oodles of Poodles 🐩🎨 business, we’ve narrowed in on “health and wellness” clients, but even that niche can be very broad.

Using the tips from the previous section, hopefully, you’ve been able to take on a few clients by this point, but since you’re still in that early stage you may have felt the need to say YES to each and every client inquiry.

That’s totally okay! But if you really want to grow, it’s time to get laser-focused on attracting a specific type of client. Think back to which clients you enjoyed working with the most, and try answering the following questions:

1️⃣ Is there a pattern to what these clients do? (Instead of “wellness companies” are most of your favorites actually yoga instructors?)

2️⃣ Is there a pattern to why they are looking for a [insert your business here] to help them? (Multiple clients have said they “don’t consider themselves creative” and “they are frustrated by trying to design their own website”.)

3️⃣ Is there a pattern to what they’re asking for? (Maybe you started out thinking you’d design 10-15 pages per website, but the best clients are happy with 4-6 pages.)

Just by answering those questions, you can paint a much clearer picture of the IDEAL customer you want to attract and how to speak to exactly what they want.

And where do you apply that lovely business-paint? You spell it out clearly on YOUR website and in all your promotional copy!

🙅‍♀️🙅 A note about saying NO to prospective clients…

At the $500/month level of business, it can be easy to fall in the trap of taking on any client that comes your way because you’re afraid to turn down money. But we found from our own experience and helping many people over the years, saying yes to clients who AREN’T your ideal customers is the quickest way to NOT enjoy your work and to muddle your messaging. The quicker you can create cohesion and clarity in your portfolio and your website copy, the quicker you will see results of more and more ideal clients coming to YOU.

⚡️ Tip #2: Develop a clear expertise.

Back when Caroline 👩🏻‍🦰 started her first online business in 2014, a design studio called Made Vibrant, she marketed herself as a do-it-all-designer (hand-lettering, logos, graphic design, print design, branding, websites, etc.) She could apply her design skills to all these different projects, so why not cast the net as wide as possible, she thought.

After working with the first few clients of Made Vibrant, Caroline went through the questions we just posed in Tip #1 and found there was a more focused approach she wanted to take.

Instead of being a do-it-all-designer designer, she realized her favorite projects were designing brands for first-time creative entrepreneurs. She loved the feeling of confidence she could see in her clients after they had a clear and unique brand identity they were proud of.

This decision to stop being a jack-of-all-trades and instead develop a clear expertise in brand design is the point where clients finally starting seeking out Caroline instead of her always needing to go out and find them. It marked a turning point in the success of her business.

This illustrates what we call the 🧲 Magnet vs 🥅 Net approach to branding your business.

👍🧲 Magnet Approach:

This approach is about being specific in stating exactly what your expertise is, exactly who you can help with your business, and exactly what makes you unique (and even a bit weird!). It’s Caroline’s version of becoming a Brand Designer. For Oodles of Poodles 🐩🎨, it’s about knowing that Squarespace sites for technology-frustrated yoga instructors is the sweet spot.

When you stop being vanilla and “for everyone,” you start to ATTRACT your ideal customers and repel customers who aren’t a good fit for you (sorry spa and gym owners, these poodles aren’t oodling for you!)

👎🥅 Net Approach:

This approach is the ole “spray and pray” idea. You’re hoping if you keep things generic enough in your copy and promotion that the right customers will fall into your lap (amidst all the wrong customers).

Yet, what tends to happen is that you don’t get any customers because people don’t know if you’re the right fit. You get stuck in place and you end up taking on bad clients and doing work you don’t want to do.

By creating more clarity in who you want to help and how you can help them, you’ll 🧲 more of the right customers for your growing biz.

Remember, don’t be afraid to “repel” people at this stage of your business. The more you can become known for doing something specific really well, the better your chances are of getting paid to do that thing!

⚡️ Tip #3: Start building an email list… TODAY.

Buckle up, buttercup! It’s time to take control of your business and build an audience of people who care about what you have to offer the world.

⚠️ IMPORTANT: Any existing service-based biz owners might be thinking, “Hey, I’ve made it this far in my business, why would I start an email list and put extra work on my plate??” And the answer is three-fold:

Why you need an email list reason #1: Building an email list helps you future-proof your entire business.

The sooner you build an engaged audience (one that’s NOT at the mercy of social media algorithms), the sooner you’ll be able to start thinking about transitioning away from trading time for money. We’ll talk more about that in the next Grow It Gradually 🦋 levels below.

Why you need an email list reason #2: An email newsletter is the simplest, most vital marketing bridge to your business.

It’s a way for you to attract people out in the chaotic catacombs of the Internet and stay connected to remind them how you can solve their problems.

By showing up consistently in someone’s email inbox (where algorithms don’t punish you), you build trust and authority with them. You also give them a constant reminder of Tip #1 (who your business is for) and #2 (what your expertise is) in this email! Read more about our concept of “Marketing Bridges” here.

Why you need an email list reason #3: Your email newsletter is a lead-building opportunity.

Using our trusty biz Oodles of Poodles 🐩🎨 as an example, we’re not just going to say, “Sign up for cute photos of Prism the poodle 🐩.” Instead, we’re going to have a bi-weekly email newsletter that shares A) a case study of an awesome yoga website and brand we found and B) a hot, new thing we learned in Squarespace. Okay, also C) an adorable photo of Prism doing something suuuuuper cute.

You want to attract 🧲 your ideal customers to your email list and consistently show up in their inbox on a schedule you can keep up with. These subscribers will hopefully become customers as you add in callouts for client availability in your emails!

⚡️ You can NEVER start an email list early enough. Trust us, even if one day in the future you were to pivot your entire business model (which we’ve done many times over the years), the right audience will move along with you. ⚡️

Having a captivated audience you can mostly control your interaction with is extremely important in business and will be absolutely mandatory to grow to the $1,500, $3,000, $5,000, and $10,000+ biz levels.

These three tips aren’t going to immediately help you jump from $500/month to $1,500/month in your business but, spoiler alert, no one has a silver bullet to help you do that.

We’re all about that gradual, sustainable growth 🦋 around here. It helps you keep balance in your life and to avoid burnout at all costs.

Next section, we’ll jump up to the $1,500/month level of business, with new tips to help you at that stage 📈.


⚡️ Tip #1: From your first few customers, can you look for patterns and identify a clear customer profile?

⚡️ Tip #2: Develop a clear skill-based expertise that people are searching for.

⚡️ Tip #3: Start building an email list… TODAY.


From $1,500 to $3,000 per month: Client Outreach, Creating an Offer, and Writing Helpful Articles

Our previous two sections have been about your client service-based business, and this section will be the last one in that arena before we start transitioning into scalable, digital products.

Too often, though, we see online biz owners try to make the leap into digital products too soon, while not building enough client runway to sustain the time that transition takes.

As a reminder, we are all about slow, methodical growth in business 🐌🐢,which often means sticking with client work for a while longer to avoid burnout and dips in business revenue.

⚡️ Tip #1: Focus one day of your week on client outreach and new client pitches.

When you’re at the $1,500 per month revenue mark with your client business, you’re probably not quite at the stage where you can cover all your bills with your profit (some folks may, and if that’s you, AWESOME 👏👏!) This is why our first tip in this section is to continually be investing time in your client outreach and potential client lead list.

Where do you find leads? Start with who you WANT to work with! Based on the previous 🦋 section’s tips, you now know the importance of getting super-specific about who your ideal client is. Use that info to search your social media channels for businesses and business owners that fit the criteria you established in the previous section.

By clearly knowing exactly who you want to work with it becomes much easier to search those clients out and put them in an outreach spreadsheet.

This leads us to this next point: Build a client outreach spreadsheet 👥

It seems like suuuuch simple advice, but we’d be willing to bet our merino wool socks most client-based biz owners do not have a client outreach spreadsheet. If that’s you, that’s okay! Now’s the time to fire up Google Sheets, Numbers, Airtable, Notion (aff link), or if you absolutely have to… Excel 😬🙈. Having a spreadsheet/database with a list of potential clients is how you keep your business organized and your leads nurtured.

🗓 Carve out one day per week to nurture your leads and create/send pitches! It is very unlikely that you’re going to grow your client roster at this stage of your business simply through your social media content creation (aka: posting on IG or TikTok) and referrals from the few clients you already have. You can’t sit back and have a, “they’ll come to me” mentality; you have to be thinking, “Let me go find them!

This is why it’s key to put time on your calendar each week to invest in the future of your business! We actually have three sub-tips to this tip’s sub-tip 😂 #tipception:

  1. 🗓 Block off time on your calendar one day per week when all you’re doing is your client outreach work.
  2. ⚡️ Also block off time on your calendar for making your client pitches (read: cold emails) STAND OUT. You have to stand out from everyone else sending pitches and that comes with creativity and effort.
  3. ⏳ Plan for a 4-6 week lead-time to land a client from your spreadsheet. In that time, build a follow-up email schedule (and social follow-ups).

New clients aren’t going to fall in your lap which means more money isn’t just going to magically appear in your bank account.

⚡️Tip #2: Get creative with your client offers!

An easy trap to fall into when you’re starting a client business is to have one core service offer (which is great!) but then not give yourself permission to experiment 🧪 with other revenue-generating ideas.

For this second tip, we want to encourage you to think about a smaller, mini offer that isn’t a huge ongoing time commitment but could bring in a splash 💦 of revenue to your biz! A gradual splash, you know? A spritz. You get it.

If you recall, our fictitious business we’ve been talking about these past few sections is Oodles of Poodles 🐩🎨, a Squarespace design company for yoga instructors. The main offer (website design and build) can take weeks of work to complete, so let’s brainstorm 3 other offer ideas that require less time:

OFFER IDEA 1️⃣: Squarespace bug fix day – For $500, you’ll spend a day ironing out any bugs on someone’s site. These could be CSS-related, email form setup, page organization, etc.

OFFER IDEA 2️⃣: Squarespace site setup – For $500, you’ll hop in someone’s brand new Squarespace account and get all their pages set up (Home, About, Blog, Product, and Contact), their blog started, and their settings how they want them.

OFFER IDEA 3️⃣: Homepage redesign blitz – For $500, you’ll redesign someone’s homepage and offer them two layouts as a refresh from what they have now.

As you can see with these offer ideas, they don’t take ongoing work and can create a nice bump in monthly revenue. If Oodles of Poodles 🐩🎨 was able to land 2-3 of these per month, that could quickly help them add $1,500 in monthly revenue without any ongoing work.

⚡️💡 BONUS TIP: If you’re a savvy offer creator, your smaller offer could be a GREAT lead-in to your larger client package. Offer Idea 3️⃣ (homepage blitz) is a great example of this and could lead to someone starting with paying $500 but then wanting help implementing the design for a larger client package!

⚡️ Tip #3: Write 6-8 foundation articles that can bring you more email subscribers today and a year from now.

We like to think about foundation articles on your website like the old Chinese proverb about planting a tree: “The best time to plant a tree was 20 years ago. The second best time is now.”

Similarly, if you’re wondering when you should get some SEO-friendly articles published on the blog of your website, the answer is as soon as possible.

Foundation articles are great for short-term and long-term (gradual) business growth.

🩳 Short-term growth – Once you have your articles written and published, you can share them on your social media channels and try to convert those folks into email subscribers. Your articles become immediate marketing opportunities. They establish trust with your audience as your followers begin to see you as a source of expertise.

👖 Long-term growth – The goal one year from now is that the almighty Google (or Bing – LOL) has seen your article(s) as helpful for certain keyword searches and you’re getting organic traffic to your site which converts into new email subscribers!

If you’ve been putting off writing articles that can build organic traffic (which lead to new email subscribers) it’s time to stop delaying this task!

What are “foundation articles?” Plain and simple, they are helpful articles that can attract your ideal customer based on problems they’re searching for on Google. Shall we take a look at some examples for our friend at Oodles of Poodles 🐩🎨? We should?? Okay, then!

  • Article topic: 3 things your website needs to book more yoga students
  • Article topic: Best practices for a yoga studio website design
  • Article topic: This is the best Squarespace template for yoga studios
  • Article topic: How to host online yoga classes through a Squarespace website
  • Article topic: Yoga website inspiration to get more yoga students
  • Article topic: How to create a yoga studio brand and website people love

These are not perfect ideas BUT there are no perfect ideas in any part of business! You want to do a bit of search term research (which we did for those 6 article ideas) and adapt what you find to fit what your ideal customer is looking for.

📌 Related: Does SEO completely baffle you!? It used to baffle us to until we learned just enough and put that enough into practice. Learn everything we know about SEO here!
📌📌 Related #2: If you want to learn our full content strategy read our Content Salad Strategy guide (with even more foundation article advice).

Next section we’re going to venture past the client-side of growing your business gradually!


⚡️ Tip #1: Focus one day of your week on client outreach and new client pitches (build that spreadsheet!).

⚡️ Tip #2: Get creative with your client offers and experiment with a mini offer!

⚡️ Tip #3: Write 6-8 foundation articles that can bring you more email subscribers today and a year from now.


From $3,000 to $5,000 per month: Validate and Build Your Digital Product

We absolutely HAVE to start this section off with a big disclaimer:


The stage of your business where you transition from clients (trading time for money) to digital products (more scalable offers) is a lot harder than most people would want you to believe.*

*Maybe those people are trying to sell you a product that makes it look “easy?” Remember that the next time you get sucked into a “how to grow your digital product biz to $X,000s in just 4 weeks” rabbit hole 😉.

The reason we give you this disclaimer is NOT to discourage you, it’s just to be HONEST with you.

The reality of online business is that it’s much harder, more stressful, and takes a ton more trial and error than you’re led to believe. We know you CAN do it, we just like to be 100% real about what it takes so that when you hit obstacles, you don’t think there’s something inherently wrong with you.

⚡️ Tip #1: Create and validate your first digital product idea.

Now that your client business is humming along, you’re probably at max capacity and can’t grow your revenue much further because you don’t have any extra time in your day/weeks to take on any more clients. This is why building a digital product is sooooooo helpful, because it’s a scalable asset that can generate revenue well beyond what you could ever make with clients and the limitations of your time.

In our experience, we’ve found some of our most successful digital product ideas have been born out of our existing client service offerings.

For example, 👩🏻‍🦰 Caroline’s brand design business could only take on so many branding clients. As she got more and more requests, she realized she might be able to teach all her branding processes in an online course that anyone could take at their own leisure. Thus, Better Branding Course was born, a digital product that eventually replaced Caroline’s brand design business completely!

How do you find a digital product idea?

How do you validate that idea?

How do you make sure it fits within your current biz?

😱 We have an entire (paid) coaching session we’re going to let you watch IN FULL right now…

Our Identifying Your Offer 💡 coaching session replay will help you come up with a digital product idea that can be the foundation of your business revenue.

⚡️Tip #2: Once you have a validated digital product idea it’s time to build it and make it available for purchase!

You came up with a digital product idea, happy dance for you 👏👏. Now, let’s build that sucker and give strangers on the Internet a way to purchase it from you. Whether you’re creating an e-book, online course, or paid membership community, these next tips should apply.

Building a digital product, boiled down into 10 not-easy-but-totally-doable steps:

  1. Write a down and dirty outline of what will be included in your product (start ugly!)
  2. Refine your outline into a cohesive structure (chapters, lessons, videos, etc)
  3. Build a creation schedule for each part of your product (put this creation time on your calendar and then DOUBLE the amount of time you think you’ll need!)
  4. Be okay with an imperfect first version of your product – NO ONE builds a great, first digital product
  5. Send your digital product to a few industry-friends who can give you feedback or thoughts (try to avoid sending to friends and family who don’t have experience in what you’re trying to do)
  6. Find beta testers from your social channels or email list to go through your digital product (this can be a huuuuge discounted price or free – your goal is more feedback and to ensure it delivers value)
  7. Take all feedback and give yourself X amount of hours to implement the feedback (but stop when you hit the constrained timeline)
  8. Build a sales page for your digital product on your website! If your website doesn’t have a built-in e-commerce option to sell things, consider using or similar to create a buy button.
  9. Write 3-5 sales emails and create a handful of social media posts to promote your new digital product
  10. Do a small “launch” of your product to your email and social audience (feel free to do a discount code for the first week of your product launch)

Annnnnnnnnd BOOM GOES THE DYNAMITE! 💥 You have a digital product in your business-arsenal! It’s a thing people can purchase from you that doesn’t require additional time investment the way your client service offers do. Hurrrrray! 🎉

Bringing back our ongoing example company, Oodles of Poodles 🐩🎨, a Squarespace design company for yoga instructors, the digital product they’ve decided on is: Squarespace website creation course for non-designers. This course will be targeted at folks who don’t have thousands of dollars to pay for their site to be done for themselves but they also don’t want to create a Squarespace site entirely on their own.

⚡️ Tip #3: Create a monthly promotion schedule for your digital product.

And here’s where the train goes off the rails for most folks who are trying to make the client-to-product leap. They 1) find their product idea, 2) make their product, and 3) sell it (ONLY) one time. And then… 🦗🦗🦗.

Life gets busy, clients pick back up, maybe the first launch doesn’t quite go very well (we’ve all been there!)

That’s where this tip comes into play and should absolutely help you generate ongoing consistent digital product revenue!

Your (new) digital product NEEDS a monthly promotion schedule. To create that consistent, gradual 🦋 revenue bump you’re looking for, it takes ongoing effort – especially early on.

Here are some digital product promotion ideas to try:

💻 Monthly free live workshops (aka webinars)

Hosting a free monthly workshop is a fantastic way to generate attention and potential buyers of your digital product. The idea is to solve a problem with the workshop topic, that people can attend for free, and then at the end of the workshop sell the digital product (which further solves the problem of the workshop).

  • Oodles of Poodles 🐩🎨 is going to create 12 workshops based on 12 Squarespace website creation tips! This is the perfect lead-in to their course: Squarespace website creation course for non-designers.
  • 👉 NOTE: If you join our WAIM Unlimited coaching program, you have access to an entire coaching session about creating live workshops (Using Live Workshops Effectively 📹🔴)

🎥 In-depth tutorials videos on YouTube

Creating in-depth tutorial videos is akin to writing those foundation articles we talked about last month! You want to identify topics your ideal customer is searching for and create helpful videos that educate them on that topic. Then, in every video, make sure there’s a call to action to get more helpful info via the digital product.

  • Oodles of Poodles 🐩🎨 could take a similar approach as used in the workshop example above and publish video tutorials on each Squarespace feature they want to highlight!

If these two ideas don’t tickle your fancy, we have an in-depth article with 13 marketing blueprints you can steal and implement for your biz.

No matter which content/marketing idea you use, the key is to do it consistently to build trust and authority around your digital product topic.

And just a friendly reminder: We started with client businesses, gradually transitioned into digital products, and now a few years later we only have digital product businesses that afford us the freedom we always dreamed of (both in time and in enough revenue).

It is absolutely possible for you as well it just may take longer than you’re being told by the “experts” out there.


⚡️ Tip #1: Create and validate your first digital product idea.

⚡️ Tip #2: Once you have a validated digital product idea it’s time to build it and make it available for purchase!

⚡️ Tip #3: Create a monthly promotion schedule for your digital product.


From $5,000 to $10,000 per month: Hone Your Messaging, Learn How To Launch, and Partner Up

At this stage in your business, it may feel like you’re in constant juggling-mode 🤹‍♀️🤹‍♂️🤹 (you’re not alone!)

Our hope for this section is to share three tips that absolutely changed the game for us, but it’s important to remember these next tips came AFTER we did all of the things in the previous sections. Notice we’re going from $5k to $10k here, NOT $1k to $10k (that’s important!)

⚡️ Tip #1: Hone your product messaging. What problem are you solving for people?

You probably read that tip and were thinking, “um, hey Jason and Caroline, how does honing my messaging help put dollar-dollar-billz in my bank account?” And to that, we would answer, “keep reading, ya silly goose! 😂”

Very quickly, let’s jump into the Wandering Aimfully (WAIM) Time Machine™ and take you back to the summer of 2019. Our WAIM business had been chugging along for almost two years, but we didn’t quite feel like we had our messaging locked in.

Here’s our exact monthly revenue back in 2019, sitting right between the $5k and $10k mark where it seemed to have stalled out:

Our exact monthly revenue back in 2019

The problem we were solving for our customers was a bit vague and our product itself wasn’t selling like proverbial hotcakes 🥞. We knew we could help transform the businesses of our customers, but that clearly wasn’t coming through in our marketing.

It was at that moment we decided to get laser-focused on what our core product should be, who it should be for, and how someone would know it was absolutely right for them.

Fast forward a few months and we did our first launch (more on this in Tip #2!) of our Un-Boring Group Coaching Program. This was the first launch of WAIM that really exceeded our sales goals, and we finally saw the traction we’d been searching for!

The first launch of WAIM that really exceeded our sales goals

So, what specifically did we change?

  1. We dialed in exactly who we wanted to help: Burned out online biz owners who were tired of feeling overwhelmed and pulled in a million different directions, without any revenue results to show for it.
  2. We created a specific product that someone could easily understand: 6 months of live business coaching, with one topic to focus on every month to grow their biz with intention.
  3. We drastically adjusted our messaging to be less about the “features”(you get course lessons, videos, PDFs, etc) to the BENEFITS (you will grow your revenue, you will feel less stressed out, you will have a plan of action, you will feel in control of your biz!)

Those three items, together, are what helped us springboard to the next level in our business revenue. It’s soooo easy to continue to use the same messaging and copy you always have, but we believe you should be auditing these things often.

💡 PRO-TIP: If honing your messaging isn’t in your wheelhouse, we highly recommend finding someone who can help you do this. Investing in this part of your business is crucial at this juncture and is worth every penny to learn who you are talking to and what benefits you are providing them!

⚡️Tip #2: Do an open and closed launch of your digital product 🚀.

Open and closed launches are one of our favorite ways to generate our business revenue (especially to create a jump in 💰💰).

If you aren’t familiar with them, an open and closed launch is simply a set period of time when you “open the cart” and allow people to purchase your product. This creates the urgency to purchase but more importantly, puts YOU in control of when you have to be in sales mode.

We shifted our WAIM biz model to bi-annual open and closed launches back in 2019, and we’ve been loving the flexibility, freedom, and predictable injections of revenue ever since!

👋 IMPORTANT NOTE: If you’re doing your first-ever launch, think of it less about just getting sales and more about learning and testing your assumptions…

🤔 Is your messaging from Tip #1 resonating with people during your launch, or are they asking a lot of questions about your product/who it’s for?

🤔🤔 Have you had a bad launch before? That’s okay! Don’t compare a previous launch of a completely different product to what you’re selling now.

🤔🤔🤔 Does selling still feel icky to you? Prove to yourself that selling doesn’t have to be sleazy and that people on your email list/social don’t mind being sold to (when what you are selling can actually benefit their livelihood!)

If you get a launch or two under your belt and your customers aren’t buying at quite the pace you expected, consider offering a lower-priced “entry” version of your product. This is exactly what we did with that 6-Month Group Coaching package we mentioned. We still had our larger ($2,000) offer, but the coaching package was $100 per month for six months ($600 total, obvs). We found the “entry” product became a solid source of immediate revenue but then also led to those happy customers upgrading to our larger product when the six months finished up.

Hey….. Guess what, chicken butt? We also have a FULL coaching session within our WAIM Unlimited program called Sales Launch Start to Finish 🚀. This coaching session teaches everything we know about launching and what we’ve learned that works really well for our bi-annual launch schedule.

⚡️ Tip #3: It’s time to utilize effective partnerships.

✅ You’ve nailed your messaging.

✅ You’ve done your first launch or two.

✅ You feel like you have all your business-ducks 🦆📊 in a row, it’s now time to find more ducks! (We know, we’re mixing metaphors in this section, it’s FINE.)

This is the tactic too many online biz owners jump to way too early in the game. They pour effort and energy into marketing, except the thing they are marketing (their offer) isn’t working that well yet so it’s (somewhat) wasted effort.

Sure, we always want you amazing humans to be doing more marketing than you currently are, but we don’t want you to expend all that effort without having all the foundational stuff in place.

That said, once you DO have your offer locked in, one of the MOST effective marketing tactics to get a bump in revenue is to partner up with someone who has a highly engaged audience in your product arena.

You want to find someone who is willing to share the spotlight with you and promote your product to their audience so they can make a sweet % of revenue without having to create your offer themselves. Your pitch to someone in this position is that you’ll give them as much as 50% of product revenue sold during the partner event and they’ll promote the initial signup of the event to their audience.

Example: Our friends at Oodles of Poodles 🎨🐩 (our example biz that does Squarespace design work for yoga instructors and also teaches a Squarespace design course) are going to partner up with a prominent Squarespace template company: Temptation Templates 💋🖥.

  • They’re going to co-host an action-packed free webinar that teaches Five Foundational Tips for Great Performing Squarespace Sites.
  • Temptation Templates 💋🖥 is going to promote the webinar signup to their audience for a few weeks leading up to the live event.
  • During the live event, Oodles of Poodles 🎨🐩 is going to lay down the gauntlet of helpful Squarespace advice and then both parties will promote Poodles’ Squarespace Design Course. Temptation Templates 💋🖥 may even throw in a free template to sweeten the deal and boost those sales.
  • They’ll split the revenue 50/50 and give the webinar attendees the option (not automatic!) to opt-in to both email newsletters for both businesses!

The great news about partnerships? There are MANY ducks in the sea! (We had to bring the ducks back and mix just one more metaphor in here).

If your first partnership doesn’t work out, figure out why. Just like one lackluster product launch doesn’t mean all launches won’t work, a partnership effort that falls flat doesn’t mean all partnerships won’t work!

And remember, especially with Tip #3, you’re NOT trying to do everything at one time. You can space these tactics out and you can tackle them on a schedule that works for your life and biz. We’re all about that slow 🐌 and steady 🐢 pace around here.

As with all of the tips we’ve been sharing these past few sections, these come from our very personal experiences.

These aren’t just theories we’re conjuring up from our business crystal ball 🔮, these are well-worn strategies we’ve implemented to help us make real jumps in our biz revenue.

We know these can work for you, it’s just about carving out the time to make them happen while having an experimenter’s mindset.


⚡️ Tip #1: Hone your product messaging. What problem are you solving for people?

⚡️ Tip #2: Do an open and closed launch of your digital product 🚀.

⚡️ Tip #3: It’s time to utilize effective partnerships.


From $10,000 to $10,000++ per month: Create a Content Strategy, Add Affiliates, and Focus on Amplification

It wouldn’t be a section in this article if we didn’t give a big, juicy caveat before sharing these last three tips with you:

Growing your business to $10,000++/month and beyond is NOT a requirement for a “successful business.”

It’s not the only way to reach your dreams and goals in life. Most of those can actually probably be done with less money (as many studies have shown). Always remember this, friend, when you catch yourself thinking your worth as a business owner can be measured in dollars. IT CAN’T.

These last tips will show you the exact steps that helped us take a leap to reach our “enough number” in business revenue, where we happily sit and don’t need to grow just for growth’s sake.

⚡️ Tip #1: Dial in your content strategy.

At this point in business, you most likely have a few content things going on: An awesome weekly email newsletter; a fun-but-helpful podcast; an info-packed YouTube channel; a pin-worthy Pinterest plan; an interestingly-designed IG grid, etc, etc.

But, what you might not have, is a clear directive and STRATEGY for each of those content buckets. You may also not have a clue if any of them are direct contributors to your revenue (if you do, kudos to you, we did not at this stage of biz 😂🤣).

Here are some examples of how to think about your content channels and having a clear plan about how they lead back to your overall sales strategy:

📬 Your Email Newsletter: This is your real-time, value-packed piece of trust-building content with your audience. You want to have a clearly defined schedule your audience can get used to as well as a specific outcome they can expect with each email they receive. Then (and this is the strategy part) make sure you have a business objective being met in EVERY email as well as a lead-up plan for your product launches.

  • Example: The lovely and talented folks at Oodles of Poodles 🎨🐩 have their Squarespace Sunday Selection emails. It’s a newsletter that contains (1) an actionable Squarespace design tip, (2) a new, awesome Squarespace template or inspiration-worthy site, and (3) a callout to purchase their Squarespace website creation course for non-designers – highlighting a different tip or lesson from the course.

🎙 Your Podcast: This is one of your strongest connection points to your audience, even though podcasting is a very passive listen. The reason it’s such a strong connection point is because it’s a somewhat intimate relationship. People listen to podcasts while living out their day-to-day lives and you get to be alongside them in those moments! You know, doing the dishes, driving to work, walking the dog, taking a shower, etc. But the trick with making a podcast strategic is to ensure you have reminders of the product you offer in each episode!

  • Example: Oodles of Poodles 🎨🐩 has an awesome podcast called Grooming Squarespace 🎙✂️. It’s a weekly show that delivers Squarespace tips and gives non-designers an insight into leveraging the platform to grow their businesses. (It’s also a clever pun for grooming dogs!) The strategic part becomes ensuring there’s always a callout to signup for the free Squarespace Tips email series, which is an easy-to-remember URL only for podcast listeners!

We think you get the idea with each content channel, but the key is to make sure you’re not just churning out content without thinking strategically of how it can impact your business.

You might be thinking, “great, I can do all those strategy things, but how do I see the actual ROI of my content efforts??”

⭐️ SUCH A GREAT QUESTION! Thank you for asking…

You create a post-purchase survey!

Using a post-purchase survey to help you understand content ROI…

A post-purchase survey is an embedded form or a linked form your customer sees immediately after buying your product. In that survey, you can ask a series of questions but one of the most important things you can ask is: “How did you hear about this product?” And you list out your content channels!

When we finally implemented a post-purchase survey (a Typeform embedded directly on our “thanks for buying” page), we found some really interesting data points:

  • 🎙 12% of our WAIM Unlimited customers find us through our podcast
  • 🎥 9% of our customers find us through our YouTube channel
  • 🤳 8% of our customers find us through our IG account

That’s AWESOME for us to learn! Mostly because a content strategy can feel a lot like being on a never-ending hamster wheel. But, that hamster wheel gets easier to ride when you can see a certain % of your revenue comes from specific channels!

The post-purchase survey is also a great way to identify any content channels you might not be loving and thinking about cutting out. If your customers aren’t finding you through a certain channel, this can give you the data point you need to stop investing time and energy into that channel 💪💪. For us, this was Instagram and what helped us decide to stop using Instgram for WAIM at the end of 2021. (And our revenue has NOT plummeted since!)

⚡️Tip #2: Create an affiliate program.

Okay, we could write a 2,000+ word article just on creating an affiliate program, but we’re going to distill it down to the actionable stuff we hope can help you right away.

Affiliates Part 1️⃣ – You absolutely need to have your product dialed in, your messaging nailed, and your entire customer journey working well BEFORE you add affiliates.

Adding affiliates to your business when things are on shaky ground is only going to cause headaches in the future (and create possible bad relationships). Our advice is to only move forward with affiliates if things are humming along smoothly!

  • 🕰️ NOTE: We didn’t add affiliates into the mix for WAIM Unlimited until the third year of our business. We had customers asking about it before then but it wasn’t the right time as our foundation wasn’t as solid as it could be.

Affiliates Part 2️⃣ – Find the affiliate platform that best fits with your website and offer.

For us, we use Affiliate WP (aff link) which is a WordPress plugin built by the same company that we use for our Membership Program (Restrict Content Pro – also aff link). There are MANY affiliate programs available so just be sure you pick the one that fits right with your website.

  • Example: The good-boy-alert dog-lovers over at Oodles of Poodles 🎨🐩 will probably use MemberSpace (with Rewardful) as they’re a Squarespace-specific affiliate

Affiliates Part 3️⃣ – Set your affiliate commission and put in effort to prepare your affiliates for success!

We do the following for our WAIM Affiliates:

  • Give a 40% commission (yes, 40% – we want it to kick ass and we love knowing our payouts can actually be a substantial source of income for our affiliates! To us, this is just part of taking care of our customers.)
  • Create an in-depth Affiliate Area walkthrough video
  • Share a “WAIM Launch Plan” with pre-written emails, prompts, and lots of information about our business they can use in their marketing to promote WAIM
  • Offer up pre-designed (and also customizable) assets to make sharing our program easy on any social platform
  • Have thorough FAQs we constantly update with common questions
  • Make asking us additional questions extremely simple and straightforward
  • Send lots of email and Slack affiliate reminders before and during our open enrollment periods!

Affiliates Part 4️⃣ – Be in constant communication to create a strong relationship with your affiliates.

The last thing you want to do is leave your affiliates feeling like they have to do everything on their own. You want to make their promotional efforts as SIMPLE as possible so it’s a no-brainer for them to promote and support your program.

As a fun note to finish off this tip, in our previous two WAIM Unlimited launches, affiliates have accounted for 50% of our new members! 👏👏👏 We’ve had a sizable jump in revenue with each launch due to affiliates and love that new customers are joining our program from existing members!

⚡️ Tip #3: Amplify the marketing bridges that are working!

Once you work through the tips of the previous section and Tips #1 and #2 in this section, it’s probably time to pour a little biz-accelerant on your marketing fires.

What content channel is working THE BEST for you?

Is it your podcast? Your YouTube channel? Pinterest? IG? Etc? Whichever one it is, you want to identify it and brainstorm ways to pour biz-fuel on that wonderful, very safe and not hot, marketing fire 🔥!

Our last example for our dog-loving Squarespace compadres: Oodles of Poodles 🎨🐩 has a weekly podcast we told you about in Tip #1 called Grooming Squarespace 🎙✂️. Poods’ has noticed an uptick in podcast listenership and has seen a good amount of people have been visiting the podcast-only page they direct people to on their website for more helpful Squarespace Tips. They’ve also done a recent launch and noticed 15% of their new customers found them via the podcast (rad!)

Oodles of Poodles 🎨🐩 is going to focus on growing their podcast listenership by trying to appear on other podcasts. They take the time to research the top 20-40 Squarespace-related podcasts (or design-related podcast where Squarespace is mentioned) and they build an outreach plan to be a guest on these podcasts – making sure they only reach out to shows who have guests. Their pitch is to appear as a podcast guest and share an actionable set of Squarespace tactics most people don’t know about. This helps the other podcast hosts know value will be given to their audience and it’s not just a random pitch hitting their inbox.

Showing up on these other podcasts gives Oodles of Poodles 🎨🐩 a chance to promote their Grooming Squarespace 🎙✂️ podcast and increase their audience!

It might not be a podcast you’re going to amplify but the key in this final tip is to look for a marketing channel that’s already having some amount of success and growth and 🔥 it up a bit!

⚡️⚡️ BONUS TIPPPPP: All the tactics in the world are useless if you can’t get things done.

We couldn’t finish the final 🦋 section with just three tips, could we??

When we get asked how we run TWO online businesses and create all the content/stuff we create, with virtually NO team at all (we do have two developers for our software app Teachery), the answer is PROCESSES.

Need to write a weekly email newsletter? Here’s our process:

  1. We brainstorm the content together and jot down bullet points
  2. I (👨🏻‍🦲 Jason) write a rough first draft in Notes app, then add it to our email newsletter template in Notion
  3. Caroline 👩🏻‍🦰 goes through the draft and makes it great 😉
  4. I take it from Notion, put it into our email provider, add in any fancy images/color formatting, and then schedule it for sending

That may sound simple, but it’s a repeatable process. It’s what’s helped us write and send 800+ email newsletters over the past 8 years.

We have similar processes for our podcast, YouTube channel, articles, IG posts (R.I.P. ☠️), monthly live coaching curriculums, customer update emails, new products we build, new features we add to our software app Teachery, etc.

We also have daily, weekly, monthly, quarterly, and annual meetings together. Those meetings have a structure to help us know what to focus on and how to keep the WAIM Train 🚂 moving forward!

Good processes, ones that you hone yourself from experience and learning from people who do the things you want to be doing, are how you can get more stuff done AND not burn yourself out.

*We do want to acknowledge that not having kids (yet) makes our output a lot easier. That’s an intentional choice we’ve made. We also want to acknowledge our inherent privileges (things like our education, upbringing, being neurotypical) that we know contribute to our ability to create processes and execute within them. We know this might not be as simple for everyone, but we hope you’ll lean into what works for your brain, your life, and your circumstances!


⚡️ Tip #1: Dial in your content strategy.

⚡️ Tip #2: Create an affiliate program.

⚡️ Tip #3: Amplify the marketing bridges that are working!

⚡⚡️ BONUS TIP: All the tactics in the world are useless if you can’t get things done.


Conclusion: You Have The Grow It Gradually Plan!

Hurrrrrraaaayyyyyyy for you making it through this Grow It Gradually 🦋 article (hopefully you didn’t just click through to this section looking for a silly GIF of us 👀😂).

There is NO straight line to success but there is a clear path we’ve followed and we believe you can follow too (with your own tweaks along the way!) Just remember: NO one jumps from $0 per month to making $10,000++ per month overnight or even in a few weeks/months.

What we’ve shared in this article is yours to come back to as often as you like! As un-boring coaches, we’re happy to support your journey as much as we can but YOU have to do the work. We can guide you and teach you from all our personal experiences but we can’t build your business for you.

You can do this.

You’ve got a plan of action.

Carve out the time and space but go at YOUR pace 🐌🐢🦋.

And now, your silly dancing GIF of us to celebrate!

A silly dancing GIF of us to celebrate

Avoid Burnout With Our Anti-Burnout Business Plan

September 19, 2022

As much as we’d like to promise you’ll never burn out again just by reading this article, that simply wouldn’t be true and isn’t something anyone can guarantee you.

What we can guarantee you, however, is that this article will help you put anti-burnout guardrails in place and assist you in the creation of a solid foundation for your business that is best FOR YOU and YOUR specific situation.

We want to share with you how we’ve learned to avoid burnout in our two businesses (Teachery + WAIM).

The goal of this article is to help you take actionable steps to avoid that dreaded moment when everything feels like too much and you have to take an extended break from your biz.

We’ve divided this article into four parts:

🤔 Part 1: Setting realistic expectations (and enough-based goals)

In this part, you get to define your enough number (and MMM number if you don’t know it). We’ll explain below what both “enough” and “MMM” numbers mean. We also recommend avoiding listening to the overnight success advice and turning your months-long timelines into years-long timelines. We believe that patience is an important part of the anti-burnout process. Embrace the idea that slow-and-steady is better than fast-and-leading-to-a-mental-breakdown.

💼 Part 2: Choosing the right business model FOR YOU

In part two, we identify the business model that’s right for YOU (and not just one you followed because of someone else’s story). We also start acknowledging that you will have to eat a few “shit sandwiches” (more on this later). We’ll share why using an experimenter’s mindset is helpful for weathering the inevitable tough moments and we want you to give yourself permission to pivot to a different business model if things aren’t working.

🙅‍♂️ Part 3: Setting boundaries (and how you can implement these steps in day-to-day business and life)

In the 3rd part of this article, we tackle setting your daily work hour boundaries. We talk about drawing your lines in the sand (days you don’t do calls, your response times, how to contact you, etc) and creating an inspiring and motivating workspace tailored for the way YOU work. In doing this, you get to define how you best work and build good habits for finding “flow.” Additionally, we encourage you to put intentional breaks on your calendar like daily walks, days off [GASP!], content breaks, etc.

🔥 Part 4: Acknowledging burnout WHEN burnout happens and putting up guardrails to help you avoid burning out again

In this final part, we acknowledge that you will burn out (or burn out again). We hope you will come to accept that WE ALL EXPERIENCE BURNOUT ❤️. We’ll finish up by talking about building your burnout savings, not allowing burnout to affect your self-worth, and defining what you need if you’re currently burned out.

Without further ado, let’s dive into the first part…

Part 1: Setting realistic expectations and enough-based goals to avoid burnout

The first key step to avoiding burnout starts with goal-setting. You may already be aware of why goal-setting is important but if you’ve run into burnout many times, it might be time to switch up your goal-setting approach.

Why goal setting matters to avoid burnout in your business

1️⃣ Not setting any goals can keep you constantly striving for more. If you don’t set any goals at all, your brain will likely fill in the gap with its familiar fallback setting: MORE. Your mind will tell you to do more, grow more, hire more, create more, and work more, without ever really asking itself what all that more is in the pursuit of. That’s a recipe for burnout, please ask us how we know 👩🏻‍🦰👨🏻‍🦲😬.

When goal-setting doesn't happen

When we don’t set goals our eyes are bigger than we’re capable of handling.

2️⃣ Huge goals with short timelines are a recipe for disaster. If you do happen to set goals, but the scale is too big in too rushed of a timeline (i.e. every “how to make $100,000* in 30 days” YouTube headline!), that is ALSO a recipe for burnout.

🙋 *Please raise your hand if you’ve bought into these lofty promises only to realize it’s A) completely unrealistic and B) totally unsustainable for YOUR life.

So what’s the antidote we want to share and how can goal-setting help you avoid burnout?

Our recommended burnout antidotes

  1. Set realistic expectations for yourself and define your goals based on an “enough” mindset. This will help you know what it is exactly you’re working toward, and what you ARE and AREN’T willing to sacrifice in order to achieve it.
  2. Creating a longer, more realistic timeframe to hit your (enough) goals is THE most important way you can avoid burning out. But first, you have to establish your enough goals so you know what the heck you are even striving for!

Creating a realistic timeframe to hit your (enough) goals is THE most important way you can avoid burning out with your business.

Setting “enough goals.”

What we mean by “enough goals” are goals that begin with you asking yourself this question:

What does ENOUGH look like in my life? (Enough money, enough subscribers, enough followers, enough time, etc.)

Your enough goals will be different from anyone else’s, but that’s a good thing! Not everyone needs to run a $100k/year business, or needs to do 5/6-figure launches, or needs to build a team, etc. Instead, it’s about defining what would be enough for YOU, individually, to live a good and satisfying life. That’s why all those folks promising you wild success in short amount of time are only going to lead you to burning out, because they’re likely pointing you in a direction toward a goal that’s supposed to be one-size-fits-all, not one that’s tailor-made FOR YOU.

An enough number for your business is an amount of money generated by your business every month/year that would accomplish all your personal goals, but that wouldn’t require you to burn out trying to achieve it.

Defining your Monthly Minimum Magic (MMM) number

But how do you begin to identify your enough number? A good place to start is by defining what we call your Monthly Minimum Magic (MMM) number. This number is your baseline expenses—just the things you absolutely need for each month. It’s the amount of money you need your business to make in order to basically break even. If you’ve never set an MMM number, we would highly recommend doing it right now. Your MMM number should include:

  • Bare bones living expenses +
  • Minimum payments on any debts +
  • Lowest possible amount of business expenses +
  • A peace of mind cushion
  • (As an example, let’s say your MMM number equals $3,500 per month)

Think of your MMM number as the LEAST amount of money you could possibly live on each month, without feeling like you have to eat Ramen noodles at every meal!

Then, with your MMM number known, tack on (realistic) extra things that would bring you to that level of feeling really satisfied and secure in your life. It could be:

  • Additional savings
  • Wealth redistribution + donation to causes you care about
  • A complete debt payoff plan
  • Future down payment for a home
  • Nice-to-haves that would improve your overall wellbeing
  • Anything else you define for YOUR life!
  • (As a follow-up example, let’s say these additional items equal $4,000 per month, your total enough number would be $7,500 per month)

Your MMM number + realistic extras = YOUR enough number

What you’ll find (we’ve seen this over and over again since we’ve been talking about and teaching folks to define enough) is that your specific enough number is less than you may think, and it’s probably also less than that arbitrary number you’ve been striving for in the past! Your previous self has been following someone else’s number, not defining what amount of money would be considered enough for YOU.

Setting realistic expectations for YOUR timeline

Now that you know what number you’re aiming for, we can figure out how long it’s going to take to achieve that specific (for you!) goal.

The online business world is far too saturated with messages about “building your business overnight” and “hitting $10k months in just a few weeks” and “creating a 6-figure business by following a few simple steps.” To be 100% honest with you, all of that messaging is garbage #sorrynotsorry.

Taking out the business trash

What we should all do with “build your biz overnight” promises.

The truth is, to succeed with your online business, it is going to take WAYYYYYY more time than you probably hope/want. Coming to terms with this fact should actually feel empowering because you can take the pressure off yourself and your business a bit. If you simply embrace and understand that you’re in this for the long haul, you can avoid the trappings of working 12+ hour days, weekends, and still feeling like you’re not achieving your goals at the pace you’re supposed to.

Instead of thinking your business has to reach some “finish line” in the next 3-6 months, what if you planned for it to take 3-6 years?

Instead of seeing a small, finite, jam-packed schedule ahead of you (that will cause you to burn out), what if you zoomed the lens out a bit and gave yourself a realistic timeline that feels spacious instead of angst-filled? If you did that, you may find yourself less focused on the short-term, immediate result and more focused on making sure the journey feels good along the way. (You can see how extending your timeline helps stave off burnout.)

Prioritizing patience helps avoid burnout

Patience and business go hand-in-hand, it’s just that no one will try to sell you an online course about being more patient because no one would buy that course. However, and we saw this ourselves when we built Wandering Aimfully, planning ahead to prioritize patience in your business approach will get you through the inevitable tough patches.

👉 Patience will help you overcome the revenue dips and lackluster launches.

👉 Patience will reassure you when the social media algorithms change.

👉 Patience will calm your brain when a successful marketing effort stops working or when a sales funnel that was working goes kaput.

The ultimate irony of anyone telling you that you can succeed overnight, in the next 30 days, etc, is that you are likely in pursuit of EVENTUALLY having a calm and profitable business. Yet, the stress and work you’d have to put in (that 99.9% of the time won’t actually get you there) to see results on this hyper-speed timeline will take your life and stress levels in the opposite direction of calm and profitable.

That’s why a 3-6 year plan to reach your enough number is the crucial first step in our anti-burnout business plan. It’s time to stop buying into the idea that you can fast-track success just because someone sells you on a new way to skip all the hard work. Hard work is where success comes from, but with proper (enough) goal-setting, timeline planning, and patience, building your business doesn’t have to be an arduous, frustrating process.

We’re happy to be riding the (slower) anti-burnout business train 🚂 and we’d love for you to join us!

⚡️ PART 1 RECAP ⚡️

Here’s what Part 1️⃣ of building an anti-burnout business takes:

  • Define your enough number (and MMM number if you don’t know it)
  • Stop listening to the overnight success advice
  • Zoom the lens out and turn your months-long timelines into years-long timelines
  • See patience as an important part of the anti-burnout process
  • Embrace the idea that slow-and-steady is better than fast-and-leading-to-a-mental-breakdown


Part 2: Choosing the right business model to avoid burnout

Building a business of ease and freedom starts with making sure your foundation actually lends itself to… ease and freedom!

No business model is perfect and different business models bring different types of stressors.

If your business is built on a foundation that requires you to stay on an endless content treadmill (like a YouTube sponsorship model, for example) when producing content is especially taxing for you, that’s a recipe for burnout. Or maybe your business model requires you to work 1-and-1 with clients when you don’t do well with other people’s expectations and schedules; that’s also going to lead you to burnout.

Identifying a business model that’s right for YOU!

You have to find a revenue-generating business model that aligns with what you enjoy doing most AND what you’re best at.

A lot of people choose a business model they think will make them successful (because, maybe someone on YouTube, Instagram, TikTok, or in your email inbox convinced you there was an “easy road to success”). The truth is, no business model is perfect and different business models bring different types of stressors.

Want to run a digital product business?

Awesome! It’s a very low-barrier-to-entry business model and if you’re a creative person with lots of ideas, this model gives you the freedom to express those ideas. However, you will have to navigate some technology to create and deliver your digital product. Then, as time goes on, you’ll probably need to update that product with new info. Also, other folks may want you to believe that digital products sell passively, but while that CAN happen, the reality is that you will likely find yourself constatntly writing sales emails, sales copy, and tweaking your sales strategy to bring in consistent sales.

What about a membership or paid community?

The recurring revenue is great with a membership or paid community, and if you love teaching or helping people in scalable way, this model can be great. But the reality is that you will need to show up for your customers on a recurring basis for them to continue to pay you. And, with recurring payments comes the admin work of dealing with failed payments and cancelations.

📌 Related reading: We have an in-depth article if you want to know EVERYTHING we’ve learned about running a paid membership community with our WAIM Unlimited program.)

Those are just two options. There are many other business types and models to explore. The key for you is to understand which one is right for your situation AND to make sure you’re up for all the challenges that any business model will bring (but maybe pick the one with the least challenges to avoid burnout 😘😘).

Which flavor of “shit sandwich” do you want to eat?

Elizabeth Gilbert talks about this idea of a “shit sandwich” in her book, Big Magic. What she means by that phrase is: there are going to be parts of any creative process that aren’t particularly enjoyable but that are worth choosing anyway. Your job is to decide which flavor of “shit sandwich” you’re willing to eat aka which sucky parts you’re willing to move through.

The truth is, when it comes to running a business, there are going to be crappy parts that take away from the joyful and awesome stuff. Find the business model or revenue strategy that feels worth it to you, even when you take into consideration the parts that are less than ideal.

When goal-setting doesn't happen

An anti-burnout business model means you’re trying to maximize spending time and energy on the good stuff you LOVE and are passionate about. But, you’re also smart enough to acknowledge there will be hard problems to solve and you’re choosing a specific business model because the positives outweigh the negatives.

What if you don’t know which “shit sandwich” you’re willing to eat yet??

You won’t know which “shit sandwich” you are willing to eat until you actually try different business models. This isn’t a bad thing. Remember, thankfully it’s a metaphorical sandwich 😆😂.

  • ❌🥪 You might find you don’t actually love selling digital products through Etsy and while it seems attractive, there are just too many parts that aren’t right for you.
  • ❌🥪 You may start selling an online course, only to realize you don’t want to talk about that content topic any longer (hello, that’s me [Jason👨🏻‍🦲] and my ‘How To Get Sponsorships’ course).
  • ❌🥪 You could fire up an awesome membership but notice quickly that the pressure to show up for customers (and keep track of their payments) is just too much for the hours you have available to work.

Sometimes the only way to discover these options aren’t right for you is to experience the burnout that comes with them, which will ultimately allow you to course-correct.

We said it before and we’ll say it again: You WILL probably burnout at some point—and sometimes that’s even the only way to know what shit sandwich ISN’T worth it—but the key is trying to have your burnout be as painless as possible and not like a volcanic eruption.

Use an experimenter’s mindset! 👩‍🔬👨‍🔬

We’ve said this for years and it’s one of the best mindset shifts we ever made in online business. It IS emotional when you’re creating your own business. You DO feel some attachment to it and it can hurt when things don’t go to plan. But… If you can always think of yourself as a scientist, constantly experimenting your way through product building, content creation, marketing, sales, customer support, etc then it becomes easier to deal with things when they go wrong.

You likely won’t be able to read this article and magically think your way to the business model that’s right for you. Instead, you’ll have to try a few versions of something, fail at a few things, and experiment through different ideas until you feel what’s right. The important part is to check in with yourself at each step of the way to see if what you’re doing is sustainable long-term.

Run your business like a dog scientist

You, as an [experimenting] business person.

When (not if, sorry) something goes wrong in your business, instead of feeling like your self-worth got punched in its gut, you can simply see it as a failed experiment: “Well, that didn’t go to plan, and it sucks, but here’s what I learned and now I’m going to do XYZ to avoid having that happen again.”

Everything… and we mean EVERYTHING is an experiment in online business. The more you can reframe everything that way, the easier the hits are to take when they come your way.

Give yourself permission to pivot to avoid burnout

And don’t be afraid to pivot! Maybe you’re running a digital product business and it’s not as passive as you’d hoped. Or maybe you’re thinking of creating a membership to shift to more recurring income? No matter where you are, take it from two people who completely blew up their businesses in 2018 and essentially started from square one. Success won’t happen overnight, but you absolutely can completely change things up and create an anti-burnout business 💪🙅🔥.

⚡️ PART 2 RECAP ⚡️

Here’s what Part 2️⃣ of building an anti-burnout business takes:

  • Identifying a business model that’s right for YOU (and not just one you followed because of someone else’s story)
  • Acknowledging that you will have to eat a few “shit sandwiches”
  • Using an experimenter’s mindset to better weather the inevitable tough moments
  • Giving yourself permission to pivot to a different business model if things aren’t working


Part 3: Let’s talk about how BOUNDARIES help avoid business burnout

We’ve talked about creating a foundation that is sustainable for you, in this next part, we’re going to focus on your day-to-day actions and how those actions can keep you from over-extending yourself.

One of the quickest ways to ride the bullet train to Burnout Town is by not having firm boundaries. When it comes to the amount of hours you work each day and what things take priority on your to-do list, it’s important to remember (if you work for yourself) that YOU are your own boss!

You make the schedule, you set the priorities each day/week/month, so it’s within your power to make sure you’re not burning the candle at both ends.

Working from home GIF

⏰ The importantance of work hour boundaries

Many years ago when Caroline was working with clients doing brand design, she found herself feeling like there were never enough hours in the day and she was always behind schedule. To solve this problem, we sat down in front of her calendar and started by asking the question, “how many hours do you WANT to work?” After some chatting, it was decided that 5 hours of dedicated client work per day was most realistic, and the hours of 10am – 4pm (with an hour break for lunch) were her most productive. From that moment forward, a boundary was put in place for those specific work hours. She started building her client proposals based on these time blocks available on her calendar. And guess what happened? Almost immediately she felt more productive and in control, as she knew when she needed to get into work mode, and then she had a stopping time each day so she wouldn’t overwork herself.

When was the last time you SET your working hour boundaries?

You may have started your business to escape the 9am-5pm schedule, but it IS helpful to have set working hours based on your lifestyle and when you want to fit work into it.

Keep in mind you can also adapt this idea for how you work best. Maybe it’s not the same exact hours each day. Maybe you need something more flexible and adaptable to your energy. The most important part is that you ask yourself the question and set the intention NOT to overwork.

Whether you’re a seasoned pro or you’re just getting started with your biz, now would be the perfect time to sit down and answer these two questions:

  • How many hours do I realistically want to work per day?
  • What are my most productive working hours?

Once you have those answers, put that schedule on your calendar the next few weeks and try it out!

🙅‍♀️🙅🙅‍♂️ What are your “lines in the sand” when it comes to work?

To set a “line in the sand” simply means to establish a boundary you’re not willing to cross.

To set a “line in the sand” simply means to establish a boundary you’re not willing to cross. It’s helpful to take some time and ask yourself, “what rules do I want to establish about the way I conduct my business?” These rules can be instrumental in not engaging in behaviors that drain you or lead you to exhaustion.

For example, quite awhile ago, I (Jason 👋) found myself on phone calls, interviews, or having online meetings on Mondays and Fridays. I DREADED THEM. Monday calls killed my beginning of the week momentum and Friday calls interrupted my end-of-week push to tie up loose ends and transition calmly into the weekend. Then, I had a moment of realization: Why am I doing this to myself!?? There’s no rule that says I have to take calls on Mondays or Fridays, so why the heck am I doing that? Pretty soon after that moment, I put a boundary in place to NOT do calls on Mondays or Fridays. If someone reached out and only had those days available, I would kindly say I don’t schedule calls on those two days but am happy to chat Tues-Thurs. There hasn’t been a single time in nearly a decade when I’ve had to break this boundary.

If you work with clients (or have customers of a digital product), one of the lines in the sand you absolutely must draw is your expected response times.

Those of you with clients have most definitely run into the late night email/text/DM where a client has an “urgent” request. But, just because something is urgent for them does NOT mean it has to be urgent for YOU. The way we learned to get around this issue is to put a boundary in place early on where you’re 100% honest about your response time. Two things we’ve done that work really well:

  1. Tell your clients/customers the turnaround response time they should expect. (I usually say to expect a response within 48 hours, even though I typically reply in the first 24 hours.)
  2. Tell your clients/customers your working hours, but make sure they know that’s their time to contact you if they need you. (“I work between 11am – 4pm each day, and am juggling a few clients, but I try to get back to everyone in our agreed upon turnaround time.”)

Just because something is urgent for your client or customer does NOT mean it has to be urgent for YOU.

One more line in the sand we think is super helpful for running an anti-burnout business is letting people know the appropriate ways they can get in touch with you.

Just because a client asks for your phone number doesn’t mean you need answer their calls or texts! If you want people to communicate with you via email, make it VERY clear what you want them to send to you in email requests (is it screenshots? Loom videos? Etc). Maybe you don’t love email and you want to create a dedicated support inbox using a service like HelpScout or even something simple like a Google Form folks can fill out. And, if you want to offer a support chat/messenger directly on your website (or in your online course), just make sure you’re setting the boundaries for when folks can expect a reply (be VERY clear it’s not “live” support).

All of these boundaries serve to set the expectation for other people about how they can engage with your business in a way that doesn’t feel overly taxing for you. That is one key to being able to continue your work long-term.

Where do you work and how do you work?

We talked a bit about time boundaries, but now let’s talk about physical boundaries.

An often overlooked part of running a business that doesn’t burn you out is having a dedicated workspace that’s separate from your life. Trust us, we’ve tried working from the couch or the dining room table MANY TIMES, but the result of this was that work too easily can bleed over into your life, consuming much of your free time to rest and recharge. Creating a separation will lead you to actually enforce those work hours we spoke about and then when you’re away from your work space, your brain will actually be able to wind down.

Even if you live in a small space, consider a spot for a tiny desk. And, regardless of the size of the desk you can fit in your home, MAKE IT FUN! The more you can enjoy the physical area you sit or stand in to crank out some work, the more restorative and energized your work time will be.

Minimal Desk Setup

That covers where you work, but what about HOW you work?

It’s key to experiment with different approaches to productivity until you land on something that allows you to get in that “flow” zone.

👨🏻‍🦲 For Jason: First thing I want to do is toss on a synthwave ⚡️ or lofi 🎧 playlist. From there, I need to close out of all ancillary applications on my computer and just have the ONE (or two) apps open for whatever task I’m working on. And how do I know what I’m working on? My Google Calendar is chalk-full of time blocks (30, 60, 90 minutes) and I don’t stray from the task at hand.

Time Blocking with Google Calendar

👩🏻‍🦰 For Caroline: First and foremost I need to know what tasks I intend to complete any given week (I keep track of that with my favorite app Notion.) Then I’ll choose an order for those tasks each day based on where my energy is at. I use the app to split up work blocks into pomodoro increments and then I put on a playlist that matched my mood and I go to town. The MOST important part of my work day, though, is that I take intentional breaks—which is our next big tip.

Free Pomofocus App

Are you taking intentional breaks? You should be!

If you’re anything like us, your work can spill over into weekends and holidays, leaving you constantly saying, “I didn’t even know it was Labor Day!?” We’ve found that taking intentional breaks from our work can be super impactful in recharging our batteries, even in small increments.

🚶‍♀️🚶 Daily walks help us clear our minds

A small daily break that has always been positively impactful for us is taking a 15-30 minute walk. Whether we end up at a coffee shop, are just circling the block, or are trekking into nature a little bit, a daily walk is a good time to step away from technology and rest our eyes and minds. You might find it hard to carve out this time, but pick something that works well with your schedule! Define this time, put it on your calendar, and be intentional about making it a habit.

The Zooks daily walk

We don’t actually take daily walks in slow motion 😅😅

🏭😴 Content breaks keep us off the hamster wheel of creation

We also take breaks with our content schedule. We intentionally pause our weekly email newsletter every summer so we can recharge those writing batteries and so our readers have the chance to get excited about our content again. We take the occasional month or even months-long break from our What is it all for? podcast too just to give ourselves time and space to feel refreshed. These intentional content breaks are absolutely crucial for staying engaged with our work, but it’s also helpful for keeping your audience on their toes and not letting that connection get stale.

Alrighty, that’ll do it for part three! Let’s get your action steps…

⚡️ PART 3 RECAP ⚡️

Here’s what Part 3️⃣ of building an anti-burnout business takes:

  • Set your daily work hour boundaries
  • Draw your lines in the sand (days you don’t do calls, your response times, how to contact you, etc)
  • Create an inspiring and motivating workspace
  • Define how you best work and build good habits for finding “flow”
  • Put intentional breaks on your calendar (daily walks, days off, content breaks, etc)


Part 4: Accepting that you unfortunately WILL burnout

In this final section, rather than give you one more tip for avoiding burnout, we thought it would be far more practical to talk about the burnout-elephant in the room, which is this: despite following the tips we outlined, you WILL likely burn out anyway. 🙈🙈

How do we know you are going to burnout?

Because the burnout threshold is different for everyone, and human instinct is to push the limit until you know what the limit actually is. We call this the “hand on the stove” moment, or that moment of pain you have to experience yourself before you know just how badly you want to avoid it in the future.

We want to offer you some tips for when burnout happens. How to soften the blow, how to be kind to yourself, and how to apply that lesson to the future.

Burnout happens to everyone 😰

Ripping the bandaid right off, let’s just be 100% truthful and honest: Burnout may not be “normal” (meaning working ourselves into the ground is not healthy) but it is COMMON. It happens to so many entrepreneurs—including us! If you find yourself hitting a wall with your work, it’s important to know there’s nothing wrong with you. It’s a predictable part of the entrepreneurial journey.

Sometimes we hit burnout because we put too much on our plates, or life overwhelms us, or we bite off more than we can (business) chew, or we just run into a string of bad luck.

This is fine GIF

Even though it’s common, that still doesn’t mean it’s fun, though! It sucks, and it’s hard to get through. But, on the bright side, the burnout experience can often be a solid life/business lesson that will make us stronger and help us avoid bigger problems in the future.

Having this mindset of acceptance towards burnout when it comes can help you bounce back with confidence (in time) and avoid any kind of shame or guilt you may experience when it arises.

Having a mindset of acceptance toward burnout can help you bounce back with confidence and avoid any shame or guilt you might experience.

What are you going to do when you burnout?

Once you accept burning out is a part of the journey, the question becomes how are you going to handle it when it arises?

Whether you’re currently experiencing burnout, are on the cusp of burning out, or are in a good place and just want to know how you should handle it in the future, the best piece of advice we can give you is this: give yourself TIME to recover from burnout ⏳⏳⏳.

As much as we’d love to tell you there’s a simple 3-step process to overcoming burnout, what we’ve learned over the years (and many burnouts) is that TIME is the only healer. Taking a break, stepping aside, completely removing yourself from the work that led you to burnout is the answer. And while that’s easy to type out in a sentence, we know from lots of experience how challenging that is!

  • What do you do for money if you can’t work on your biz?
  • How do you continue to move toward your goals if you’re completely spent?
  • How do you separate your self-worth from your business, especially in a down time?

Those are all great questions and they all come with answers that are different for everyone. We can’t guarantee our advice will be perfect, but we can tell you what’s worked for us:

💸 How do you make money when you’re burned out?

It could be dipping into your savings. It’s why you save, after all—for one of those rainy days (and with burnout, there’s a 100% chance of [metaphorical] rain on the forecast). If you don’t have savings, it boils down to figuring out what you can do for money that can sustain you. Is it selling stuff around your house? Is it asking a friend to hire you for low-pressure contract work? Is it moving back home to build back up with less overhead? All of these options are on the table and none should be ignored.

🎯 How do you work toward your goals when you’re burned out?

Honestly… your goals get put on hold when you’re burned out. There’s NO sense in trying to continue to push forward or make progress, you must rest and you must be okay with the fact that the pause button is your only button. In these situations, it’s important to remember you’re taking one step back to ultimately take two steps forward. In that regard, you ARE still working toward your goals, you’re just making sure you’re in a healthy, energized head space in order to go after what you want.

🤗 How do you separate your self-worth from negative burnout feelings?

This one is sooooo difficult because when you work for yourself it’s incredibly hard to separate your work from your worth. The best advice we can give you is to repeatedly remind yourself that your work is not tied to your identity. Your work is a set of experiments in a scientific lab of sorts. As soon as you leave that lab (your work), you are your own person with a separate identity. What happens in Vegas the lab stays in the lab!

It’s really hard to hear, but again, TIME is the only answer to overcoming burnout.

Allow yourself a break, and do whatever you must to survive and get by in the meantime, because the harder you push against burnout, the longer it will take to overcome (and the more damage you may be doing in the process.)

What guardrails are you putting in place for yourself?

Okay, let’s say you’ve burned out, you’ve given yourself time to recover, and you’re feeling good again… now how the heck do you avoid burning out again!??

Well first, read the previous parts of this article 😘. The second thing to learn from your last bout of burnout is to understand what may have gotten you there. Then, put up some strong guardrails to help you avoid falling off the burnout cliff in the future.

  • Do you need better boundaries around your working hours?
  • Do you need better client processes?
  • Do you need more efficient productivity practices?
  • Do you need to completely pivot your business?
  • Do you need to quit and take a bigger break?

Only you are going to know what guardrails are most important for you, and it’s important you don’t ignore the mistakes of your past.

Only you are going to know what guardrails are most important for you, and it’s important you don’t ignore the mistakes of your past. We’ve certainly experienced burnout multiple times for the same reasons, and it’s not like you’re going to fix things perfectly after burnout, but you should absolutely try!

How to avoid the “shiny new” brand of burnout? (Hello, TikTok, etc.)

The last part of avoiding burnout is being able to recognize when you’re pouring your energy into a business tactic that isn’t sustainable.

This is especially dangerous when a shiny new opportunity comes along and you feel pressure to a) take advantage of a marketing channel that can get you disproportionately high organic reach or b) hop on the bandwagon because you see other business owners doing it.

Shiny object SQUIRREL

It’s easy to get caught up in trends, especially when your previous efforts may not have worked well, and then something new clicks and you start to see a lot of momentum. You want to ride that bullet train toward your goals and hold on for dear life! But, if you go too hard and invest too much time and energy in something new, all your foundational things can easily get left behind (goals, processes, boundaries, healthy habits, basic biz stuff, etc).

We’ve been there: The new thing emerges, you start to feel a positive change in your business, and you want to do everything in your power to grab ahold of that bucking bronco and soak up as much growth as you possibly can. However, if something new is taking up all your precious resources, something is going to have to give in its place. That’s when you typically end up burning out, even if you’re generating the most revenue, the most audience growth, and the most notoriety you’ve ever had.

We DO want you to notice the experiments that are working in your business!

We DO want you to enjoy the success those things bring! But, we also want you to remember you are trying to build an Anti-Burnout Business and to have something that sustains you for the long-term, not just a flash in the pan.

When it comes to shiny new burnout, just keep in mind your processes and your goals. You may need to reconfigure both of those things and you may need to reprioritize what really matters, but that’s the key: Embrace the new awesome thing, but be intentional with how all of that time and effort fits into your existing day-to-day.

⚡️ PART 4 RECAP ⚡️

Here’s what Part 4️⃣ of building an anti-burnout business takes:

  • Acknowledge that you will burnout (or burnout again)
  • Start building your burnout savings now (and/or create a plan)
  • Decide what guardrails you need if you’re currently burned out
  • Be prepared for the new shiny object burnout


In Conclusion, Your 19-Step Plan to Avoid Burnout

Here are all nineteen tips we shared in this article to help you avoid burnout in the future and build an Anti-Burnout Business 🙅🔥:

1. Define your enough number (and MMM number if you don’t know it)

2. Stop listening to the overnight success advice

3. Zoom the lens out and turn your months-long timelines into years-long timelines

4. See patience as an important part of the anti-burnout process

5. Embrace the idea that slow-and-steady is better than fast-and-leading-to-a-mental-breakdown

6. Identifying a business model that’s right for YOU (and not just one you followed because of someone else’s story)

7. Acknowledging that you will have to eat a few “shit sandwiches”

8. Using an experimenter’s mindset to better weather the inevitable tough moments

9. Giving yourself permission to pivot to a different business model if things aren’t working

10. Set your daily work hour boundaries

11. Draw your lines in the sand (days you don’t do calls, your response times, how to contact you, etc)

12. Create an inspiring and motivating workspace

13. Define how you best work and build good habits for finding “flow”

14. Put intentional breaks on your calendar (daily walks, days off, content breaks, etc)

15. Acknowledge that you will burnout (or burnout again)


17. Start building your burnout savings now (and/or create a plan)

18. Decide what guardrails you need if you’re currently burned out

19. Be prepared for the new shiny object burnout

We hope that you are able to take actionable steps to avoid burnout from this article. As a reminder, reading an article does not promise you’ll never burn out again. But what we can guarantee is that you now have the knowledge to help you put anti-burnout guardrails in place and assist you in the creation of a solid foundation for your business that is best FOR YOU and YOUR specific situation!

Our 2021 Year-End Review and 2022 Preview

January 25, 2022

2021… you went by so slowly and yet so quickly at the same time.

Another year in the books, folks! While 2021 felt a lot like 2020 in many ways, we were incredibly grateful to make it through some fairly rough patches and also some really great moments too.

2021 summed up in a GIF:

2021 felt like everything was fine

We love doing these year-end reviews as it helps us zoom the lens out and see the good, the bad, the ugly, and the in-between. It’s also really interesting to review these… reviews… as the years go by. If you’ve never written one of these, we highly recommend it (even if you don’t share it publicly).

Last year’s review had a callout to a (100% free) Notion Yearly Planning Template and we wanted to share that again. We’re biased, but we think it’s a solid way to go through end-of-year planning 🤗😉.


🎙 Want to listen to the podcast version of this Year-End Review? You can do that using the podcast player below or you can queue this episode up from our What Is It All For? podcast in your podcast player of choice.


What Went Well In 2021? 👍

👩🏻‍🦰 Made consistent exercise a priority (and learned not to hate it!)

This was my one big personal commitment to myself in 2021, and I feel really proud to say that I was able to follow through on it. I’m no longer a person who hates to exercise! Hooray!

I want to be 100% clear here in stating that this goal did not come from a place of wanting to change my body, needing to hit a certain number on a scale, or the belief that exercising regularly somehow makes one a better person than anyone else. We have enough of that crap messaging being launched at us from the diet industry and the media.

For me, this was about a few things instead:

  1. I know from experience that regular exercise helps me manage my anxiety. Maintaining good mental health is the most crucial priority to me, so learning to not hate it seemed like a pretty worthy endeavor.
  2. I wanted to change this recurring self-perception and narrative that has popped up my entire life telling me I’m not capable of caring for myself in this way. One of the childhood stories I continue to work on in therapy is this idea that I am “weak” and I wondered if challenging this belief in this way could help reinforce a sense of self-trust and some lived experience to rewrite that internal self-criticism.

I’ve tried to work on establishing this habit for years, but it’s never stuck. I think the biggest reason I was able to finally to make it happen in 2021 is that this time, my desired change was coming from a place of self-love and not self-hate. My motivation was not to chase down something I felt I was lacking; it was born out of a deep desire to care for myself. This major difference meant that I approached everything from a place of compassion, joy, and curiosity, rather than making it about strictness, punishment or disappointment. And that little bit of grace was enough to keep me coming back.

I made up my own rules and I kept the expectations low. Just ten minutes a day. And yes, even stretching for ten minutes or a restorative yoga session “counted.” I would cross off a big X for every day I completed to track my streak. If I felt like pushing myself one day, I would. If I had zero motivation and just wanted to dance around in my garage for ten minutes, I would. If I got bored with an exercise session and “quit” after ten minutes, great! Totally allowed. Because I showed up. And the only person who was there to judge me was me. It was always about whatever I needed that day, and that’s how I was able to turn it into a daily habit.

This year, as we travel, I know it will be harder to keep this habit alive but I’m committed to trying because I know just how positive the impact has been on my life.

Caroline Zook working out

Caroline Zook workout goals achieved


🚀 We reached our “Enough Number” and had our best WAIM Unlimited launch yet!

In 2018, we agreed on an “Enough Number” for our monthly business revenue: $33,000. This number wasn’t just plucked out of thin air because it sounded good on paper; it was intentionally chosen based on clearly outlining our realistic financial and lifestyle goals. (Also, keep in mind, that number is revenue, not profit. 👍) We thought it would take us one year to achieve it when we started WAIM, which honestly seems laughable at this point, but, hey, these two kids can dream!

On September 28* of this year, this goal became a reality! 🎊🥳🎉

*100% honesty moment: During our launch when we hit our enough number, we were barely able to celebrate it due to some personal family issues that took us on a two-month emotional roller coaster. Life has a funny way of balancing out our emotions, huh?

You can read all about our Journey to Enough here (with the first update starting at $0 per month in revenue). In the 2022 preview section below, you can read why we’re actually updating this enough number three years later, not as a means to keep growing for growth’s sake, but just to adjust to the vision we have for this next phase of our lives.

WAIM’s monthly revenue increased 127% from 2020 to 2021

In the lovely chart below, you can see the monthly revenue line for 2020 (in magenta) and our awesome new revenue line for 2021 (in blue).

What feels most amazing about this chart to us is that our work output was probably LESS in 2021 than it was in 2020. It felt like we really found our groove in 2021 with our bi-annual launch model (Spring and Fall).

Wandering Aimfully 2021 MRR Chart

In 2021, WAIM Unlimited welcomed in 266 new customers (49% increase from 2020)

In looking back, 2020 was actually a solid year for WAIM. We saw consistent growth and ended the year with 165 new customers. But, 2021 saw an awesome increase thanks mostly to our affiliate program.

Wandering Aimfully 2021 New Customers Chart

Of those 266 new customers in 2021:

  • 167 came from affiliates (63% of total customers)
  • 16 came from our “passive” email sales funnel (6%)
  • 21 customers canceled their WAIM membership (6.7% churn for the year)

Speaking of customer churn, we made some great strides this year in reducing cancelations!

Any time you increase new customers, you’re likely to see more churn. However, in 2021 we saw a 44% reduction in churn from 12% in 2020 to 6.7% in 2021.

We strongly believe the decrease in churn boiled down to a few factors:

  1. Many new customers came via affiliates, which is usually someone they trust and know will lead them to buy something worth investing in
  2. We feel our business model is very dialed-in these days and new customers know exactly what they are going to get on a monthly basis
  3. We’ve continued to evolve our sales page and email sales copy to be extremely honest, transparent and lacking in psychological/fear-based tactics

Wandering Aimfully 2021 User Churn Chart


📊 Our email metrics are UP but our website traffic is DOWN 🤔

It’s weird to put this in the “what went well?” part of this review, but it feels like it was a good thing, so let’s run with it for now (we’ll check back next year on those feelings 👀).

Total new website visitors in 2020: 353,021
Total new email subscribers in 2020: 3,145
Traffic to email conversion in 2020: .08%

Total new website visitors in 2021: 206,574 (⬇️ 41% decrease)
Total new email subscribers in 2021: 4,469 (⬆️ 42% increase)
Traffic to email conversion in 2021: 2%

Here’s a look at our new email subscribers broken down over the course of the year. Two fun tidbits for all you tidbit fans out there:

  1. Highest day of subscribers: 46 people on September 5
  2. Lowest day of subscribers: 1 person 🤣 on July 17 (no days with zero tho!)

Wandering Aimfully 2021 Daily Email Subscriber Chart

We doubled our website conversion rate and nearly doubled our new email subscribers while seeing a 41% decrease in website traffic

When you compare our website traffic numbers from 2020 to 2021 it can feel like this:

Grimacing GIF

But, when you break down the metrics that matter most for our business to thrive, it actually has us feeling like this:

Zooks Dancing GIF

Over the years, we’ve had a handful of articles that really pumped up our website visitor counts. BUT, the majority of those articles weren’t serving the core focus of WAIM that we’ve been moving into (un-boring and thoughtful business coaching). As those larger trafficked articles started to slump we noticed the traffic, decreasing but our email subscriber rate actually increased!

While we only published five new articles in 2021 😋 (our goal was 12), they were high-quality articles and would target our ideal email subscriber (and hopefully, eventually WAIM Unlimited customer). We also did some tweaking on a few existing articles and hope to see the fruit of those traffic trees in 2022. We’ll check back on that next year!

We also did our annual email purge and deleted 6,000+ subscribers 💪💪

Every year we do what’s called a re-engagement email campaign to our email list. It’s a series of four emails sent over the course of 20 days. In those emails, we ask subscribers who don’t seem interested in our emails to click a link to stay subscribed.

This year, that campaign (and some other cleanups) removed 6,000+ subscribers from our list. This task used to scare us, but now it empowers us. It keeps our email list healthy and reduces our monthly bill with our email provider (nearly $1,000 in savings coming our way in 2022!)

Wandering Aimfully 2021 Subscriber Chart


✨ We created two new products this year: the Notion Starter Pack and Page Layout Library

Everything we create these days is for our WAIM Unlimited members. While we still have a few straggler products out in the ether, we spend zero time on those and make very little revenue from them (no surprise in that correlation). When we make a new product, it’s to help improve the lives of our WAIMers!

🧴 The Notion Starter Pack

Notion has REALLY been a game-changer for us. Maybe you’re drinking the kool-aid too? They’ve just done such a great job of building a productivity tool that is powerful yet flexible, and it works really well with our brains. We laugh all the time while asking ourselves, “how the hell did we get anything done before Notion??”

The Notion Starter Pack is our own cobbled-together Notion system. We took parts that we learned from other awesome Notion folks (h/t Marie Poulin and August Bradley) and built something unique to us and the way we manage our business/life blend in one system. We built this system and test drove it ourselves for six months before we launched it in Spring of 2021, including it as an added bonus during our WAIM Unlimited enrollment.

During that Spring enrollment, we saw 15% of new customers say they joined because of the Notion Starter Pack. If we extrapolate that out, it equates to ~$40,000 in total revenue. Not bad!

Wandering Aimfully Notion Starter Pack

📐 Page Layout Library

A difficult task that can often delay launching ideas within your online business is layout and copywriting for your website. Whether it’s your home page, about page, sales page, etc, it can be a mental grind to know what to put where especially when you’re starting with a blank page.

While we know there’s no “one-size-fits-all” right way to design a web page, we wanted to make it easier for our WAIMers to get pages designed and live so they could continue experimenting to see what worked for their unique audience. We created 10 page layouts that include step-by-step prompts to write compelling copy as well as design and layout advice for each page (and section within it). Within 24 hours of launching the Page Layout Library we had a few WAIM members who had turned an existing homepage or about page from something they weren’t excited about into a page they LOVED. That’s exactly what we wanted this project to do, so we call it a success 💪.

And yes, if you were wondering, the library was built using Notion!

Wandering Aimfully Page Layout Library


🗺 Committing to our dream of travel and building a plan

Departing from the world of business (see what I did there??), let’s talk about huge life changes.

As of writing this year-end review, we are planning to move to Europe and live abroad for all of 2022.

This has been in the works for five years and for obvious reasons it didn’t happen last year. With the current omicron variant of COVID, we of course have to be mindful of taking every safety precaution to try and make sure we stay healthy as we travel, and more importantly, to make sure we don’t thoughtlessly spread this disease to others as we travel who may have less protection. As of writing this, we are triple-vaccinated and our first destination has almost 90% of its citizens fully vaccinated with a much lower hospitalization rate than the United States. These are things that will stay top-of-mind for us as we travel and we will consider the risks with every decision we make, not just for ourselves but the people we come into contact with.

WAIM Around The World

Where are we planning to travel in 2022??

That’s a great question, and one we’re kind of keeping close to the vest. As you can probably tell by these review articles we share A LOT, but this is one instance where we want to keep a bit of mystery.

We can tell you that our travel plans look like this:

  • We’re planning to spend 2ish weeks in each spot
  • We’ve currently booked everything through March 25

And we can also tell you that our priorities in choosing destinations are as follows:

  1. We’re not interested in big cities, so we’ll mostly be going to smaller cities
  2. We’re not interested in museums, site seeing, etc, we want to try to live like locals
  3. Food and great restaurants are HIGH on our list (we may have booked one destination just on its food alone)
  4. Fun Airbnb options that will feel unique and different in each country
  5. Balancing between city life, country life, and seaside life

🎥 Will we be documenting our travels? 📸

We will!

Video – We’ve decided we want to try to record and upload one travel video from each location to our YouTube channel.

Instagram – We’ll be sharing some travel updates on our Instagram account @wanderingaimfully.

Podcast – We’ll definitely be sharing more behind-the-scenes stories on our weekly podcast.

Email List – Our weekly email content hasn’t been decided on yet with how much we’ll be talking about our travels. It might just be the place we share links to the podcast, YouTube, etc. The jury is still out on this one and we’ll figure it out as we go!

What did we have to do to get ready to become full-time travelers for a year?

The first thing was simply committing to this enormous life change. When we moved across the US from Florida to California in 2015, it wasn’t an easy decision. Leaving your routines, comforts, family, and friends behind is daunting just to think about… let alone DO!

Once we got over the mental hurdles of making this big change, it was time to do all the practical stuff. I’m going to boil it down into some bullet points, but just know it was not as easy as these simple statements make it seem 😵‍💫😵‍💫😵‍💫.

  • We sold… EVERYTHING. Well, 99% of everything.
  • We had one three 📦s we sent to my Mom with a few memory items and important papers.
  • We sweet-talked friends into storing Caroline’s first large canvas art piece (thanks Caleb and Jen!)
  • We whittled our possessions and wardrobes down into 2 roller suitcases and 2 travel backpacks.
  • We ended our rental lease.
  • We sold our car.
  • We updated our address to a virtual mailbox and changed it on all. the. things. (Twice, because I screwed up the first time 😤.)
  • We canceled all our US insurances and got travel insurance.
  • We stayed as grounded and levelheaded as possible during that entire process 🥵😂.

Needless to say, the final two months of 2021 were very busy and full of small emotional moments realizing how much our lives were about to change!

We sold all our stuff!


🍿 Our “Classic” Movie Night Continued!

Okay, the last item of business in this section, but one of our favorite things we do together as a couple. On Saturday nights we hunker down, pick two movies from the 80s, 90s, or 00s, and just enjoy the time together.

Here’s the highlight reel from 2021’s watched movies (2020’s movie highlights are in that review if you are dying to know what movies we watched last year and loved):

  • The Guest (our favorite rewatch of the year – suuuuuch a fun and unique thriller!)
  • Virtuosity (omg, what a ride of a movie – truly a gem!)
  • 2012 (just a really great disaster movie)
  • Skyfire (not nearly as good as 2012 but definitely entertaining)
  • Taken 1/2/3 (Liam Neeson doesn’t disappoint)
  • Scream 1/2/3/4 (while mentioning an enjoyable series, Scream ✅)
  • Away We Go (for the Enneagram 4s out there + the soundtrack is great!)
  • The Net (Sandy B, you nailed all that computer hacking!)
  • Sudden Death (Caroline actually enjoyed this JCVD classic)
  • Volcano + Dante’s Peak (super fun to watch volcano disaster movies back to back)
  • Dune (the new one… not the classic… absolutely FANTASTIC movie)

We’ll see if we keep up with this ritual as we travel in 2022. Every time we think we’re running out of movies we find another genre we forgot about (like volcano disaster flicks 🌋🤣).



What Didn’t Go Well In 2021? 😰

✋ Content warning: If reading about COVID-19 is triggering for you or you struggle with family trauma and don’t want to read about ours, please feel free to skip these next two sections.

🦠 COVID-19 hit our family pretty hard

When I finished writing last year’s year-end review, I knew the odds were that someone close to us would likely be hit with COVID, we just didn’t know it would happen so soon after hitting publish. Unfortunately, one of our most vulnerable family members who lives in Florida ended up hospitalized for 5 weeks starting in January of 2021.

This was before we were eligible for the vaccine, so traveling back to Florida unvaccinated amidst the largest (at the time) case numbers didn’t feel safe or responsible to us. That made the experience especially hard because you can’t really do much from far away except provide emotional support to your other family members and FaceTime as often as possible to help someone through it. Of course, we know just how lucky we are that this family member was able to get good healthcare and survived two rounds of pneumonia throughout those five weeks. We know other families were not this lucky, and we just want to take a moment to say our hearts go out to you if you have lost someone you love during this pandemic. We know the collective pain everyone has gone through is immense.

Though our family member survived 🙏, the lingering effects of COVID on them are still present a year later, and this continues to inform our decisions as we try to balance navigating COVID-era life and mitigating risk at the same time.

We are fully vaccinated and boosted as of writing this review. If you are able to do the same, we highly encourage it to keep our more vulnerable communities safer.


💔 Complicated family interactions derailed the end of 2021 for us

Without getting too specific on this one, we’ll just say that family relationships can be incredibly hard to navigate as you get older. We grow up and sometimes it becomes clear that the way our family of origin systems functioned when we were kids wasn’t always healthy. As an adult, trying to set boundaries to protect yourself from harm within that system can be extremely difficult, and we found ourselves entangled in this after our trip back to Florida post-vaccination.

Again, we’ll spare you the details for sake of privacy of those involved in this, but we felt it was important to share because it was a HUGE part of our year and it left both of us in a very tumultuous and at times low mental health state for the last quarter of the year. Thankfully, we were able to move forward through it (with the help of Caroline’s awesome therapist!) and ultimately will look back on this last part of the year as a very transformative time when old patterns and ways of being had to be shed in order to make room for new, healthier ways of being.

*I do want to add a note of positivity here. We DID get to hug our Moms (and other family members) for the first time in nearly two years and that definitely was a highlight of our trip back to Florida.

Hugging our Moms in 2021


🥴 Did we mention Caroline got shingles for a 2nd… and 3rd time in 2021??

Soooooooo… yep. There’s a reason we didn’t write a year-end review for 2019 and it’s because it was the hardest year ever for Caroline. She dealt with terrible anxiety and depersonalization for almost the entire year on top of getting severe shingles for the first time.

The only silver lining to 2019’s bout with shingles is that 👩🏻‍🦰 is acutely aware of what it feels like when shingles is starting to flare up. There’s an unmistakable sensitivity to a localized area of her body, and she immediately can detect that something isn’t right.

The 2nd shingles battle happened after our family member was in the hospital with COVID. And the 3rd shingles battle happened a few weeks after our October trip and difficult family interaction. HUH. Seems to be a (shitty) pattern emerging here. We know that as a Highly Sensitive Person and someone who has an anxiety disorder, Caroline is highly susceptible to internalizing emotions and this often has very real physical consequences. We are both learning how to support her through this when it happens, and how to accept this as the reality. Being sensitive has incredible benefits and tremendous value, but there are unfortunately costs as well.

Anyway, again, not trying to be a Debby Downer, just sharing the reality that is life for all of us (ups and downs). We feel very fortunate that Caroline knew shingles were creeping up both times, and both times she was able to get the medication she needed early, which prevented the painful rash from developing like it did the first time.

Sucks that shingles came around twice this year, hopefully, that means it’ll skip the next 30 years?? 🤞🤞🤞

Caroline Zook in her shingles perch


🖥 Let’s transition to business: we didn’t have time for a passive income project

For two years we’ve had this itch to create a smaller passive income project. Not because we want to make more money—we have pretty modest financial goals for this project compared to our other businesses. It’s really because we believe in diversification in business, and we love experimenting with new business ventures so we continue to bring value to our WAIM members.

We finally landed on an idea we felt good about for a new biz venture, but it always fell to the bottom of our priority ladder. The sad part is, we REALLY like the idea! It seems like something fun, fairly low investment of time, and right in our technical + creative wheelhouse. It’s just, there wasn’t enough time this year with everything else we wanted to do.

Maybe you’re like us and you’ve had a side project staring you in the face for years, but you simply can’t muster the time to work on it? We’re here to tell you that’s 🆗. It’s more important to keep your mental and physical health in check and focus on having a strong business foundation before adding yet-another project to your mix (we’ve definitely fallen into the trap before).

Instead of pushing ourselves to make this project happen, we simply accepted we didn’t have time for it. We won’t have time for it in 2022 either, but that doesn’t mean we can’t revisit for 2023! We shall see.


⚙️ Last item in this section, we definitely didn’t make as much progress with Teachery this year

For those of you reading this who have no idea what Teachery is, it’s a small SaaS (software as a service) that helps people build and sell online courses. It’s been around since 2014 when the idea popped in my head to build an online course and I couldn’t find a platform I liked. In 2020, we spent the entire year redoing the branding and interface of Teachery which was wonderful! A difficult task indeed, but it created a really solid foundation for Teachery moving forward.

We had some fairly lofty goals for Teachery in 2021, most of which were NOT financial. Instead, they were features we wanted to create and launch. Given the last few sections you just read, you might understand why we didn’t accomplish our goals with Teachery this year.

But… We’re not too upset about this. Would we like to have gotten more features out the door for our awesome Teachery users? Heck ya! But, we still knocked a few features out and made some solid infrastructure improvements along the way.

We’re trying to keep our goals with Teachery very modest and realistic in 2022, as traveling full-time won’t afford us much extra bandwidth to work on features or marketing. It’s something we want to prioritize in the future, just probably not next year.

The good news is, word of mouth continues to grow Teachery’s revenue slowly and steadily 🐌📈🥰…

Teachery Revenue 2014-2021



📜 2022 Preview (What’s Next?)

🌏 Full-time travel: Wish us luck! 🤞

As of writing this review, we’re just days away from departing on a year of living out of two suitcases and two backpacks. We are SO excited, but also nervous at the same time (COVID doesn’t help that, obviously).

We’re hopeful we’ll be able to leave, make our way over to Europe, and bounce around feeling as safe as possible.

Be sure to subscribe/follow our YouTube Channel, Podcast, Instagram, and email list if you want to hear about our adventures!

🥐 Side goal during travels: My hope is to try a cinnamon roll in every destination we hit. I hope to find the best cinnamon roll in the world (okay, not really, but it seems fun to try to find one in every place we go!)

Editor’s note in January 2022: We’ve officially made it to our first destination! WAHOOO!

WAIM Around the World - Zooks in Europe


👨‍💻👩‍💻 WAIM: Maintain what we did this year and deepen the connection with our members

WAIM is working as a business! (Honestly, there were times the past few years when we would have DREAMED to be able to say that!) We’re able to deliver value to our members each month, and we’ve found a reliable system for growing our revenue through our bi-annual launches.

It will be interesting to navigate our live monthly coaching sessions from Airbnbs around Europe. That could get a bit hairy, but we’re not stressing out about it until we have to.

If you’re a WAIMer and you’re reading this, we heart your face REAL HARD. We hope to keep bringing you helpful, un-boring, inspiring business content all year long in 2022! 😍😘


💸 $57,000: Our new monthly “enough” number

Okay, whoa, whoa, whoa. You might be thinking $33,000 -> $57,000?! What’s the deal?! That’s a huge jump! But, allow us to add some context.

We aren’t just doing this just because we want more money to buy Jason cinnamon rolls. Three years after setting our first goal, we need to adjust this number because:

#1 It costs more money to make $33,000 than we thought

When we set that original revenue goal in 2018, we had no idea that WAIM affiliates would ultimately be the driving force of our revenue. In fact, in the original breakdown of our $33,000 enough number, we earmarked $5,000 for our total average business expenses and $3,000 for our total average taxes to set aside.

To put those initial cost projections into context, now that we actually hit that $33,000 per month revenue number, we pay $10,000 per month just in affiliate payouts (which we LOVE doing). But that means our profit is much lower than we projected in 2018. Also, our taxes nearly tripled from our original estimations 😬. So, that’s the first reason we need to adjust that number to account for the costs associated with reaching our desired profit.

#2 We have different life goals for the next chapter of our lives than we did in 2018

Taxes and affiliates are enough to justify the enough number increase for us, but we also want to build a larger savings buffer (especially after watching family members get hospitalized, and let’s just be honest, the US healthcare system has the power to put any one of us into a very precarious financial position.)

We want to save up a down payment for our first home together, and account for the fact that we want to have children in the next few years (we’re told they cost just a bit of money, right? 🙃)

You can see in this chart that while the difference between the $33K to $57K seems like quite a jump, for our lifestyle it ultimately boils down to a $3K/month increase in mortgage, a $2K/month increase in living expenses (hi, kiddos!), and a $2K increase in our savings contributions.

You may not have read our enough number article so we just want to remind you that our goal does not have to be your goal, nor should it be! And, we don’t share our goal to be aspirational. We share it to be honest, transparent, and to demystify the conversation around money.

Oh, last note here, we aren’t sure what the timeline looks like to hit our new monthly $57k enough goal. Will it happen in 2022? Probably not. Might it take 3 years like our last enough goal? Keep reading these reviews to find out!


🙏 Hoping everyone is healthy (by your own standards!) and happy (also by your own standards! 😉)

Given the new variants of COVID we saw in 2021 and the continued uncertainty of this disease, we hope you, your families, and your friends are staying safe and taking as many precautions as possible. Wishing everyone a healthy and happy 2022—whatever that means for you given your circumstances!



🗄 Let’s Wrap It Up! How Are We Framing 2022?

Each year we pick a word that helps us frame the next year. The word becomes a mantra and we’ve done this since 2015!

👩🏻‍🦰 Caroline’s word(s) for 2022: Discomfort and Magic

When I thought about what over-arching theme and intention I wanted to set for this year of flux and adventure, I couldn’t limit myself to just one word, as I usually do. So the TWO words I’ve chosen to guide my 2022 are DISCOMFORT and MAGIC.

First, discomfort. I know this year is going to present me with so many situations that challenge my comfort. Going places where I don’t speak the language. Sleeping in a different bed every few weeks. Taking more flights than I have in years. All of these things are potentially anxiety-inducing, and as someone who struggles with an anxiety disorder, that scares me.

AND YET… the past few years I’ve assembled an array of tools that make me feel capable of weathering that discomfort. I trust myself enough to take care of myself in this sea of uncertainty, and I’m actually excited to challenge my own limits. I’ve learned that the more I practice being comfortable with discomfort, the more resilient I become and the more my world expands. I’m eager to stretch myself in that way, as I know it will benefit me throughout the rest of my life.

Embracing discomfort though is only one aspect of why we want to take this trip. I wanted a second word that would speak to the more joyful benefits that happen AFTER you do the scary thing. I wanted a kind of guiding “why” behind all that discomfort. And that’s where MAGIC comes in.

Amidst the uncertainty and anxiety of next year, I want to stay ever-mindful of the delightful, unexpected, and exciting moments that will undoubtedly arrive. I want to notice the magic of a jovial shop owner; the reflection of the sun on the water of a coast I’m seeing for the first time; a new cuisine; a cobblestone street; a helpful stranger. I want to collect these little magical experiences as I go and make sure that as I’m learning to live in this more transient way, I’m staying open to noticing these tiny rewards for making myself uncomfortable.

👨🏻‍🦲 Jason’s word for 2022: Absorb

We are going on a HUGE life adventure in 2022 and I want to soak as much of it in as possible. My nature is to optimize and do things as efficiently as possible and I’ll be fighting those urges at every turn. Having the word absorb as my focus should help me to slow down, take a beat, and not worry about how much faster something can get done.

It’s not lost on both of us how amazing of an opportunity traveling full-time is. I want to savor as much of it as I can, each and every day!

Are you writing a “Year-End Review”? We’d love to read it!

If you decide to write your own Year-End Review post feel free to send it to us via email (head to our contact page).

We hope you enjoyed reading our review! 👋👋

Step-By-Step Guide to Hosting Better Live Workshops

July 8, 2021

Have you always wanted to host a live workshop but feel intimidated by it? We’ll guide you through the process of building curriculums, live trainings, and webinars that grow your audience and turn them into paying customers.

Just to get on the same page when it comes to terminology, when we say live workshops, we’re using it as a blanket term referring to:

  • Webinars: Teaching a topic with a sales call-to-action, like selling a course, at the end.
  • Workshops: These could be free with no strings attached OR a paid workshop to bring in revenue.
  • Trainings: Teaching to existing customers, like our Wandering Aimfully Coaching Sessions! #shamelessplug

Basically live workshops

Basically, live workshops are all about teaching something in front of a camera to further your business.

Some of the many reasons we’ve loved hosting live workshops over the past 10 years:

  • 🤝 They create a direct connection with our audience
  • 🦄 We love teaching things while also having fun
  • 💸 Live workshops are an effective way to deliver value and sell products or services

Whether you want to build an audience, deepen your trust with your customers, or sell a product or service, there’s one thing that helps you achieve all three of those things…

… establishing authority.

Establish authority with live workshops

Live workshops allow you to establish authority because they’re about showing someone you have the skills to solve a problem for them.

Your customers (or potential customers) have a pain point and it’s your job to use your expertise to make that pain point go away.

Think of your customers or your audience like someone who has a specific problem or pain point. Your customer is searching for someone WITH AUTHORITY to help them alleviate their pain.

That’s where you come in!

You use your knowledge and expertise to alleviate their pain through live workshops. Think of your live workshops as if it’s your doctor’s appointment with them and the goal is for them to leave with some relief.

You customers (or potential customers) have a pain point and it’s your job to use your expertise to make that pain point go away.

We’ve divided this live workshop guide into four parts:

🔨 Part 1: Creating your live workshop curriculum

This is your bag of solutions to ease your audience’s pain AKA your workshop topic and curriculum.

📽 Part 2: Learning the live workshop tech

You have to learn to use the tools at your disposal to best help your audience. We’ll go over all the tech specs (workshop software, microphones, webcams, etc) to make your workshops top-notch without breaking your bank!

📡 Part 3: Going live!

This is where you actually ease your audience’s pain. We’ll share best practices for running your live workshops and how to set up replays.

💰 Part 4: How to effectively sell during a workshop

We’ll walk you through how to use your live workshop to actually sell a bigger solution to your audience’s pain.

Let’s dive right into it!


Part 1: Creating Your Live Workshop Curriculum and Presentation

First up, let’s talk about a critical piece of live workshops…

You need to have a clear goal for WHY you are hosting a live workshop.

Here are some different ways to use live workshops based on different goals:

Live workshop goals

Across the top of the table, you have different end goals for your live workshop that depict the journey of your potential customer through your marketing bridge*. Your live workshops can either be set up as Free or Paid, depending on your goals.

Note: We really dislike the phrase “sales funnel” around here so we refer to that concept as creating a Marketing Bridge. You can learn more about how we think about marketing and get 13 free marketing bridge ideas in this related article.

🎯  Live Workshop Goal #1: Brand Awareness (free)

You can have a live workshop that is all about building brand awareness. It could be something you host on Instagram Live, Facebook Live, or even inside a Facebook Group.

🎯 Goal #2: Email List Growth (free)

Then, you can have a live workshop that is behind an email sign-up but you’re not doing any selling. We used to do this in a series called “Transparent Talks” which was just a way for us to deliver value through a monthly training session and get people to sign up for our email list.

🎯 Goal #3-A: Sales (free)

You can also do a live workshop to teach and then sell a product or service at the end. We’ve done various free live workshops to sell our Wandering Aimfully Un-Boring Business Coaching (a $2,000 product). I,👨🏻‍🦲Jason, used to host a weekly free live workshop and sold an online course at the end. Remember, the live workshop itself is free but you generate revenue for your business by landing a few sales of a paid product at the end of the workshop.

🎯 Goal #3-B: Sales (paid)

You could sell a paid live workshop where the offer is the live workshop itself. We’ve done this a handful of times, creating a simple sales page to promote the paid live workshop and selling “seats” to it. This is a great way to get a cash injection in your business AND to validate an idea for a bigger product you might be thinking of building.

🎯 Goal #4: Customer Trainings (paid)

Finally, you could do a live workshop as a part of a paid program or a course like we do with our Wandering Aimfully Un-Boring Coaching Sessions. Here’s a look at our coaching dashboard we’ve created for our members which features the upcoming live workshop and the past recorded workshops:

Wandering Aimfully Coaching

Your live workshop goal should be one of these things:

  • 📣  I’m doing live workshops to build my brand awareness and email list.
  • 💞  I’m doing free live workshops to deepen the connection with my audience and establish trust.
  • 🤑  I’m doing live workshops to teach something and then sell a product/service that teaches MORE on that topic.
  • 🥳  I’m doing live workshops because I run a paid offering and it’s how I show up for my customers.

By setting a specific goal for your live workshop, it becomes easier to be satisfied with the result of all your effort.

Now that you know what goal you want for your live workshop, let’s talk about building your curriculum!

Remember, this is like your bag of solutions you’re going to use to ease your audience’s pain and build authority with them.

First things first, you have to come up with a live workshop topic

When you’re coming up with a workshop topic, you have to think of your goal and think of your audience (potential customer).

If you’re trying to 📣 build your awareness…

  • Where do you see a need in the market or a topic that people seem eager to learn about based on content you’ve already created?
  • What blog post or article have you created that people are already attracted to?
  • Is there a specific piece of social media content you’ve created that people are engaging with the most?

Answering these questions will give you a range of topics that people want to learn about from you.

For example: If you have a Virtual Assistant Business and you want to target busy entrepreneurs and you noticed that your blog post on Asana is getting a lot of traffic, your workshop topic could be “3 Ways to Save Time in Your Biz Using Asana.”

If you’re trying to 💞 deepen the connection with your audience to establish trust…

  • What skill have you honed that’s led you to create your own process/way of doing something?

For example: If you have a Digital Planner Business and you know that one of the pain points of your audience is that they don’t have enough time to customize and personalize their planners, you can create a live workshop on “How to Customize & Embellish A Digital Planner in 15 Minutes.”

If you’re trying to 🤑 sell a product/service…

  • What small problem can you solve that leads to the bigger problem that your offer solves?

For example: If you have a course on Selling Printables on Etsy but you know that the initial problem most first-time sellers need to solve is how to even get started on Etsy then it would make sense to build a live workshop on the “4 Steps To Getting Your First Printable On Etsy.”

If you’re trying to 🥳 show up for your customers…

  • Ask your customers! What topic would bring the most value to them and what do they need from you?

As an example, we do this a lot in Wandering Aimfully! We have loads of ideas for our coaching sessions so we ask our members which topics are most interesting to them. That’s exactly how we came to one of our workshop topics “How To Use Live Workshops Effectively.” 😉

👋 Caveat: We don’t believe in teaching second-hand knowledge. Teach from YOUR experience or a process you’ve created. If you don’t have enough knowledge, experiences, or a unique process… create one. This is your chance to start learning stuff now so that you can teach it later. Remember to stick to your values and listen to your gut on what feels right to YOU.

Live Workshop Topic Example: Using the “Instagram Algorithm” to Your Advantage

Let’s look at the Instagram live workshop we did to promote our Wandering Aimfully coaching program because our coaching session at that time was all about setting up an Instagram strategy.

If your goal is a workshop that sells an offering, use the “iceberg” concept to come up with your topic.

Live workshop strategy

The topic of your paid product or service is ALL this good stuff beneath the surface of the water. For our case, it’s our 2-hour coaching session where we teach an entire Instagram strategy. It was only available inside our paid coaching program.

The topic of your workshop is just ONE pain point that’s connected to your bigger topic. In our example, we chose the topic “3 ways to use the Instagram Algorithm to your advantage” as our little iceberg on top of the surface. Then, we sold our coaching program that will teach them everything else beneath the surface.

Another way to think of this: your workshop is like a band-aid and your paid offer is the cure.

Now that you have your topic, how do you even begin to make your curriculum?

We have a general formula for running a successful live workshop based on years of experience:

  • Problem: Start with the problem you’re solving
  • Intro: Then introduce yourself and your experience
  • Preview: Preview what they will learn in the workshop
  • Teach: The bulk of your workshop is the teaching portion (duh!)
  • Pitch: if you’re doing a pitch, give this plenty of time and space
  • Q&A: And finally, we love a good Q&A (and so will your audience)

Here’s an example of how the formula works for a 60-minute sales webinar:

Live workshop structure and timing

Hellos & Welcome (5 mins): Greet people and ask a couple of icebreaker questions as you wait for attendees to trickle in.

Problem, Intro, Preview (5 mins): Start with the problem you are going to solve for them and tell them why they are here. Then do your introduction after that and tell them why you are the person who can solve the problem for them. Finally, give them a preview of what you will be teaching in the workshop.

Teaching Section (25 mins): This is the bulk of your workshop! Your priority here is to deliver value and the solution to the problem you introduced earlier.

Pitch (10 mins): Yes, you are going to spend ten minutes selling your offer confidently. You made a thing that is awesome so spend time on pitching it!

Q&A (15 mins): Answer questions from the attendees on the workshop topic or your offer.

💡 PRO TIP: Add subtle reminders and cues throughout the workshop to bring the audience’s attention back to the workshop. It can be something as simple as asking them a this-or-that question or gently telling them to go back to the workshop if their attention has veered off to social media.

Our process for creating your live workshop presentation:

Live workshop presentation process

Step 1: Outline:

Create a Google Doc and brain dump all of your ideas into it. Don’t worry about organizing anything, just get your thoughts written down (bullet points are great).

Step 2: Organize

Once your outline is done, go back through your brain dump and organize your thoughts into sections. Try to group thoughts together. Try to break things into three to four “acts” or parts.

Step 3: First Draft

Open up your presentation app of choice and roughly add your slides based on your sections and bullets. DON’T get caught up on the design or formatting yet. This process will go so much faster and smoother if you just take your organized first draft and get them into your slides.

Step 4: Design

Finally, add design and branding to your slides! Format all headings and add slide transitions (get those star wipe transitions!) You can add all the design, GIFs, and transitions but remember that the content should be the star of the show.

💡 PRO TIP: If you are someone who tends to dive into design first, try putting together the content first and show it to a trusted friend before you do any design on it. Ask them if the content is helpful and if they give you the thumbs up, then you know it’s time to move on to design.

Some live workshop teaching best practices:

  • Think of the final result you want for your attendee and then reverse engineer your information and sequence based on that final result.
  • Structure things in three or four “acts” so it’s easier for people to follow along (think: Step #1, Step #2, Tip #1, Tip #2, etc).
  • Studies show people retain information better when it’s attached to a story so it might be worthwhile to think of a metaphor that you can use throughout the workshop.

This could be a separate article on its own but…

Let’s talk about basic slide design for your live workshop presentations

We’re not here to teach you how to move from MS Paint 🎨 to the modern era of design tools but we do have some helpful tips we’ve learned from hosting 100+ workshops over the years.

Basic Slide Design 101

  • Bring items in one by one. Do not display everything on a slide all at once, it’s overwhelming. Less is more! Err on more slides with less info.
  • Headings are your friend. Vary your font sizes to create headings and body fonts.
  • Stick to 3 fonts at most. Just because 10,000+ fonts exist doesn’t mean you need to use ‘em.
  • Use photos/illustrations. Services like Unsplash, Over, and Adobe Creative Cloud Express (formerly Adobe Spark) are great for adding visual interest.
  • Do not be afraid to use impact slides. These are simple slides with only one sentence on them and a bold color that breaks up your content.
  • Add some fun! GIFs are your friend! If you’re feeling saucy, you could even add video 😱 (but only if that doesn’t overwhelm you).
  • Be careful with templates. Canva, Envato, Creative Market, etc offer great templates but don’t go overboard!
  • Keep transitions SIMPLE and consistent. Star wipes are wonderful in theory but distracting.

🔥 HOT DESIGN TIP: Keep in mind the design of the page you’re embedding the replay in. For example, if your website has a white background, you might want your presentation to have a different color background or border so when it’s played it doesn’t disappear on the page.

Let’s Recap Part 1:

  • Determine the goal of your workshop.
  • Understand your customer’s pain points.
  • Come up with a workshop topic based on your goal and audience’s pain points.
  • Build out a teaching curriculum that helps bring your audience “relief.”


Part 2: Figuring Out Live Workshop Tech

It is soooooooo easy to get distracted by all the technical bells, whistles, and gear that can help you deliver a great live workshop.

❌ Don’t get distracted! ❌

Your content is the star of your live workshop show; the gear and the tech are the supporting cast.

We love gadgets and goodies as much as the next person, but we’ve also used the bare minimum and still had great results. Be willing to upgrade AFTER you gain more experience (and revenue).

We’ve put together a couple of audio, video, and lighting recs whether you’re on a budget or looking to splurge and invest. Most of them are affiliate links and we make a small commission if you buy using these links.

📹 Best Webcam for Live Workshops

No Budget: Use whatever laptop camera or webcam you already have. Boom, done, congrats to you!

Low Budget: Anivia 1080p HD Webcam ($45). Highly rated and solid price point.

Higher End: Logitech Brio 4K Webcam ($199). This is our webcam of choice these days but we only recently upgraded to this.

Best Webcam for Live Workshops

🎙 Best Microphone for Live Workshops

No Budget: Any headphones with a built-in microphone are better than nothing!

Low Budget: RODE SmartLav+ ($70). Great lavalier microphone that’s also unobtrusive. We used two of these for years!

Higher End: Sennheiser MKE600 mic with Manfrotto Boom Stand ($560). This is what we use but it’s overkill unless you do a lot of video.

Best Microphone for Live Workshops

🕯 Best Lighting for Live Workshops

No Budget: Find natural light in your space and sit in front of it! This is what we do 99% of the time for our workshops 👍👍.

Low Budget: Selvim 6-inch Selfie Ring Light ($33). Has a desk clip as well which is neat.

Higher End: Dazzne Desk Mount Key Light ($199). Lots of color range and a ton of light.

Best Lighting for Live Workshops

⌨️ Misc Gear for Live Workshops

There are so many little items that make workshops easier to run but these are the 3 things that we use MOST often and wanted to recommend:

Wireless Trackpad: This is great for clicking through slides and not having to click keys on your keyboard. We’re on Apple laptops so we use the Magic Trackpad.

Second Screen: Great for keeping up with comments, Q&As, or ensuring you stay live the entire time. We just use one of our iPhones or iPads for this!

Wire-In to the Internet: From years of experience, trust us, if you can hardwire in using an ethernet cable, DO IT. We didn’t know our Apple laptops just needed this USB-C ethernet dongle but now we do.

Misc Gear for Live Workshops

🤓 PRO GEAR TIP: Do a couple live workshops with no budget or low budget items and make sure you even like doing them. There’s absolutely no point in buying a bunch of gear if you find out you don’t even like the experience of hosting live workshops.

⚙️ Best Software for Hosting Live Workshops

👩🏻‍🦰👨🏻‍🦲✅ Our choice: Zoom Webinars ($79/mo). Zoom has the most stable connection, has all the features you need, and seems to have the least amount of outages and issues.

WebinarNinja ($49/mo): Full disclosure, we are friends with the creators of WebinarNinja but that’s not why they get our recommendation. This is a solid, all-in-one platform that is extremely robust and always being improved.

Crowdcast ($29/mo): We used to use Crowdcast a ton. They have fantastic customer service and a really nice user interface. The only problem? We would run into some sort of technical hiccup from time to time. They may have sorted this out over the years as we haven’t used them since 2019.

Best Software for Hosting Live Workshops

💻 Best Program for making Live Workshop Slide Presentations

👩🏻‍🦰👨🏻‍🦲✅ Our choice: Keynote (Mac). We absolutely love Keynote and how flexible and intuitive it is. PLUS, you can record your presentation directly in it for great replays!

Google Slides or Canva: If you can’t use Keynote, Google Slides or Canva are robust free slide presentation tools with many of the same features.

Microsoft Powerpoint: Maybe Powerpoint has gotten better since we last had to login to it almost two decades ago?? We have no idea 😂.

Best Program for making Live Workshop Slide Presentations

🪞 How to create a great recording space in your home

Let’s talk about a few tips to create a visually interesting (read: not-distracting) backdrop for your live workshops…

Move things around: Your plants, furniture, pictures on the wall! Be okay with temporarily decorating a part of your home to ensure your workshop backdrop isn’t too distracting. We do this every month in a corner of our home for our live workshops!

Set a budget: If you are going to buy a few things for your workshop recording area, set a budget and don’t go nuts. You can always upgrade more later on down the road.

Avoid blank walls: Blank walls actually make video backdrops drab and boring. Find a spot where there’s some character behind you. Pro-tip: Do you have a larger painting on a wall somewhere else in your house? Take it down and lean it up against the wall behind you like we do!

Jason Zook and Caroline Zook

Let’s Recap Part 2!

  • Choose your video, audio, and lighting options according to your budget/experience.
  • Decide on the software you’ll use to create your slides and to host your actual workshop itself.
  • Construct a workshop backdrop that’s visually interesting!


Part 3: Preparing To Teach Live and Workshop Replay Tips

Let’s talk about some best practices for delivering an awesome workshop! The biggest tip we can give you while you’re live and presenting…


You’re going to have bullets in a lot of your slides. Remember to stick to those core points and don’t veer off on a 5-minute tangent.

If you’re nervous about hosting a live workshop, we’ve got your back!

This is especially for all you Nervous Nellies! To fend off nervousness during your live workshop:

  1. Just read your bullets. Don’t go off track.
  2. Have some emphasis slides to create impact and break up the bullets.
  3. Practice, practice, practice, so you know your slides really well.
  4. Show your personality but don’t try to deliver a comedy routine if that’s not something that comes naturally to you (be yourself but bring some energy!)
  5. Did we mention sticking to reading the bullets on your slides??

This is where all the work in Part 1, where you wrote and organized your workshop content, comes into play. Make sure you craft your slide bullets in a conversational tone so that when you read them during the live workshop, you won’t sound stiff or like a robot.

💡 PRO-TIP: If you’re hosting your first-ever live workshop, ask a friend to watch a practice version. Tell them you want their honest feedback and wear your feedback-armor when they tell you what needs improving. Additionally, you can do a dry-run of your workshop, record it, and watch it back… what did YOU think needed improvement?

Create a GO LIVE Checklist you can refer to before every workshop

✅ 🔋Are all your devices charged, in Do Not Disturb mode, and ready to go?

✅ 🐹 Are your kids, dogs, cats, okapis, all wrangled-up and away from distracting you?

✅ ☕️ Make sure to have ample fluids available.

✅ 🎵 Queue up your favorite pump-up jam and dance around a bit 10-15 minutes beforehand! (This sounds silly but it’s actually very useful for getting your adrenaline going so you can dive into the workshop pumped up and energetic!)

  • 👩🏻‍🦰 listens to Taylor Swift or Whitney Houston
  • 👨🏻‍🦲 listens to Outkast, Lil Dicky, or Daft Punk

✅ 📝 Have your GOING LIVE Checklist written next to you (what buttons do you need to push, what things need to be recorded and how, is your second screen setup, etc).

Don’t forget to set expectations for your viewers – you’re their guide!

How should people interact during the live workshop? Tell them how to use the chat and really guide them on how they should behave during the workshop. We like to do this in the Hellos & Welcome portion of our workshops. We tell people exactly where the chat is, how they can interact with one another, and that we like to answer questions at the end using the Q&A box.

Tell people when they should get ready to pay attention. When you’re getting into the meat of the teaching portion, tell your viewers to get ready to take notes or get ready to answer live questions from you. Remind them multiple times throughout when you’re making an important point.

Live workshop attendee attention

If there’s a sales pitch, make sure you give people a head’s up! We don’t like to bait and switch our live workshop viewers so we always tell them, in the beginning, there’s a pitch at the end. We also give a head’s up when the pitch is about to start so people can leave if they don’t want to be sold to.

Reminder: Something WILL go wrong during your live workshop 😩. Prepare for this. You’re probably not a pro at live workshops so give yourself permission to mess up!

We’ve hosted enough live workshops over the years (100+) that we can unequivocally tell you unfortunate things WILL happen. Your workshop software craps out. Your dog barks wildly. Your slide presentation won’t load. Just do your best to explain to your viewers what’s going on and they’ll appreciate the honesty and realness.

What about live workshop replays??

🔥 Hot take on live workshop replays: We don’t believe in expiring or limited-time replays.

Someone may have taught you otherwise or you’ve seen this practice in action time and time again. However, we simply don’t believe in expiring replays (“The webinar replay is only available for 48 hours!”)

We get it, people need urgency and scarcity to make a purchase but use the countdown timer to take advantage of a limited-time offer not watching the replay.

Hot take about webinar replays

🔄 There are two main live workshop replay options to choose from:

Option #1: Live Platform Hosting

Let your live workshop software (Zoom, WebinarNinja, Crowdcast, etc) host the recording for you and simply link to it.

  • Pros 👍 Almost zero effort on your end and the replay is probably immediately available.
  • Cons 👎 Harder to add a limited-time offer to the replay “page.” Watching environment usually isn’t great or branded.

This option is HIGHLY recommended if you are A) a beginner at live workshops and/or B) not very technically savvy. It’s not the lesser of the two options, it’s just less customizable.

Option #2: Self-Hosted (this is our choice)

Download the recording from the workshop software, upload it to your video host of choice, and put it on a page on your site you can customize to your liking.

  • Pros 👍 Gives you total control of the replay watching experience and is especially great if you have a limited-time offer to add to the replay page.
  • Cons 👎 Takes longer and requires extra effort and technical know-how.

Options for webinar replays

Let’s Recap Part 3!

  • Stick to your bullets and keep your slides moving.
  • Make sure you write out a checklist ahead of time for exactly what you need to do when you go live.
  • Check-in with your audience periodically during the workshop.
  • Don’t sweat it if something goes wrong!
  • Make sure you have a plan to deliver your replay.


Part 4: How To Use Live Workshops To Sell Your Product or Service

As a friendly reminder, we use “workshop” and “webinar” fairly interchangeably around our household. We’re going to refer to your live workshop as a webinar for this section.

Your webinar: This is the temporary relief you offer your viewer for their pain point. It’s the tip of your iceberg.

Your product or service: This is the CURE to the problem! It’s not just a band-aid/quick fix, it’s the solution and the entire glacier sitting below the water.

How to think about webinars

Your quick, 3-bullet summation of using a webinar to sell a product or service is as follows:

  1. Create a webinar registration page and drive traffic to it.
  2. Teach a few helpful things on your live webinar, then sell your product or service that fully solves the problem.
  3. Have a limited-time offer and sales page + sales email sequence.

Pretty straightforward, however, there are many steps that go into those three bullet points. Don’t worry, wegotchu!

A simple step-by-step process for creating a webinar that actually sells

Steps to running a webinar

Step 1: Create your webinar sign-up page.

The purpose of this page is to get people to sign up for the webinar and get excited to learn something from you.

Here’s a very simple registration page layout we mocked up to show you the main components you need:

Webinar registration page example

Keep it simple: The page needs to be incredibly straightforward (no distractions, no social icons, nothing but the register button!)

Don’t hide the time/date: The time and date of the webinar need to be crystal clear. Bonus points if you want to use a timezone converter to help your registrants.

Post-signup thank you page: There should be a thank you page after registering that tells them to add the date of the webinar to their calendar. If you want to add social sharing icons for the webinar, put them on THIS page.

Reminder emails: Your registration system should send reminder emails about the webinar (most platforms offer this as a built-in feature).

Step 2: Promote sign-ups by driving traffic to your sign-up page.

Use your existing email list and social media accounts to get people to sign-up for the webinar!

Send multiple signup emails: We recommend sending multiple emails, at least 2-3 weeks ahead of time, getting people to sign-up.

Create your social promo content: Create multiple social media posts that promote the webinar, but also give people actionable tips to intrigue them to want to learn more (link in bio!)

Be descriptive and entice people: Whether it’s email or social, don’t just say “sign up for my webinar” − address the pain point you’ll solve and tease people with helpful info.

Here’s an example webinar promotion schedule:

Webinar promotion schedule

Step 3: Create your curriculum/presentation.

Bust out your presentation tool of choice and create an awesome and helpful webinar!

Webinar structure and timing: Follow the structure we outlined in Part 1. Here’s that image again for ya…

Webinar structure and timing

Practice your little buns off: Run through the presentation LIVE with a friend and watch the recording back. Make notes on how you can improve. Practice, practice, practice!

Be proud to sell your product or service: Do NOT skimp on the sales pitch part of the webinar. You did all this work, don’t shortchange yourself and undersell your offering.

Here’s an example of webinar slides we’ve used in the past during the sales portion (these all have bullet by bullet or sentence by sentence slide-builds so it isn’t just one giant slide with too much info on it):

Webinar sales slides example

Step 4: Create your Replay Page.

If you’re going with Replay Option #1 (hosted by the webinar software), make sure to grab that URL and add it to your post-webinar sales email sequence.

💡 PRO-TIP: You’ll get traffic to your webinar registration page well after your live webinar has already happened. Think about updating this page to deliver the replay to someone if they still want to “sign up.”

If you’re going with Replay Option #2 (self-hosted on your website), make sure you:

  • Have your replay page designed and ready to go
  • Have your process in place to download the replay from the webinar software and then upload it to your video host
  • Have your sales section on your replay page with your limited-time offer
  • Have double-checked all links, buy buttons, etc!

And, some additional tips for you if you’re creating a self-hosted replay page:

  • Remind people of the outcomes they will learn by watching the webinar replay (30-40% of replay watchers don’t attend live).
  • Include the slide presentation as a PDF they can download. Use to compress PDFs.
  • Make your call to action (your limited-time offer) VERY CLEAR to get someone to the full sales page for your product or service.
  • Add a countdown timer for the limited-time offer (not the replay). Just remember to remove the limited-time offer buy button on the replay page when the countdown expires.

Webinar replay page example

Step 5: Create your Limited-Time Offer sales page.

If you want to sell using a webinar effectively, you want to create some sort of urgency in your limited-time offer for your product or service.

🚀 Launch offer: If your sales webinar is part of an open/closed launch, cool − there’s your urgency (although you might want to throw in a bonus to sweeten the deal!)

🌱 Evergreen offer: If your sales webinar is for a product or service that’s normally evergreen (available all the time to purchase), think about a bonus you can throw in to really make the offer feel time-sensitive. This does NOT have to be a discount and could be something like a 1-on-1 call, group Q&A, or another product you throw in the mix.

Step 6: Host your webinar.

Use what we already discussed to prepare for your webinar, interact with your audience and nail your sales pitch!

  • Keep in mind the pain point of your attendee − what problem are they seeking solutions to?
  • What is the “band-aid” solution you’re offering in your webinar? Make sure your teaching content delivers on that promise.
  • And what is the “cure” solution your product or service promises? Make sure your pitch communicates that clearly.

Webinar checklist

Step 7: Send your post-webinar sales emails.

For every one that registered for your webinar (attended or not), you want to queue up and send a series of sales emails. You gotta pay your bills!

For example: Let’s say you want to leave the cart open for one week after the webinar…

  1. You’ll send 4-6 sales emails starting the day after the webinar.
  2. Each email should be helpful in some way and not just a pitch to buy. You want to always be delivering value.
  3. Each email should have a very clever call to action to go to the sales page AND mention the deadline to buy.
  4. If you can avoid it, don’t send any “normal” email newsletters to this group during your sales sequence.

This is what your post-webinar email schedule could look like:

Webinar email sales sequence

Step 8: Wrap it up and shut it down!

Shut everything down and make sure any pages that have countdown timers are no longer available for purchase.

  • We like to turn any sales pages into email capture pages after the limited-time offer expires.
  • When doing email capture, make sure to have a Welcome Email that lets them know they’ll get your normal email newsletter moving forward.
  • Take time to decompress, relax, and reflect on how everything went.
  • Think about using your webinar replay as an evergreen marketing bridge in the future!

Let’s Recap Part 4!

  • Make sure your sales workshop topic is the band-aid to your offer’s cure.
  • Know your sales strategy before, during, and after your webinar.
  • Don’t shortchange yourself on the pitch!


Live Workshop Wrap-Up: Let’s Not Forget About Mindset! 🧠

All the tactics and strategies in the world won’t help you if you don’t have the right mindset! Running a live workshop is A LOT of work (as you’ve read) and it’s important to get your head in the game ahead of time 😆.

🧠  Mindset Tip #1: Increase live workshop confidence with practice.

You are going to be nervous if you don’t host live workshops often. That’s normal! We even get nervous and we’ve done 749 live workshops at this point. The more practice you have, the easier it will be to “go live.”

🧠  Mindset Tip #2: Have realistic goals based on YOUR audience size.

Depending on the size of your email list and social media following, you should expect 3-5% of your total audience to sign up for a webinar.

Example: If you have 500 email subscribers and 500 followers on social media, 5% of your audience would be 50 webinar registrants.

🧠  Mindset Tip #3: Something will go wrong.

We’ve done this enough times and almost every single live workshop we do has some sort of hiccup. Mentally prepare yourself for this. It’s not the end of the world. Just roll with the punches and do the best you can.

🧠  Mindset Tip #4: You can always host another live workshop in the future.

If you have a live workshop that flops, especially one where you tried to sell a product or service and didn’t get any sales, don’t give up! We’ve had complete flops and then six months later had a super-successful workshop.

🧠  Mindset Tip #5: Remember your marketing bridges.

Live workshops are just ONE marketing bridge on your journey of getting strangers on the Internet to buy from you. Live workshops may be a bridge to another guidepost on a customer’s journey to find your castle!

Phew, that was a lot to throw at you! We know that live workshops can be intimidating if you’re not used to being on video but trust us, once you’ve gone live again and again, it DOES get easier.

We enjoy incorporating live workshops into our business because it’s an incredibly effective way to grow our audience, deliver amazing value to them, and convert them into happy, paying customers.

Our 2020 Year-End Review and 2021 Preview

December 17, 2020

Well, we certainly don’t have to sugarcoat the fact that 2020 was a rollercoaster of a year.

If this is the first year-end review you’ve read from us, these reviews are as much for you as they are for us. We love reflecting back on the year to see where we’ve just come from so we can make informed decisions on where we want to go.


In years past, these reviews were scribbled in digital docs, cobbled together in random notes/boards, and while they had some structure, it was a bit of a hot mess. But, hot mess no more!

We’ve created a Yearly Planning Template in Notion that you can use 100% fo’ free (and you don’t even have to submit your email or jump through 27 hoops to get it!)

Click here to grab the Notion Template or click the image of the template below. Duplicate the template for yourself and fill it out/answer all the questions at your leisure!

Yearly Planning Notion Template


🎙 Want to listen to the podcast version of this Year-End Review? You can do that using the podcast player below or you can queue this episode up from our What Is It All For? podcast in your podcast player of choice.


What Went Well in 2020?

👩🏻‍🦰👨🏻‍🦲 2020 marked our 10th year together!

It’s hard to believe that one Twitter DM back in 2010 led us to where we are today. This is one our first photos together in 2010 and it couldn’t sum up our relationship any better, 10 years later:

Jason and Caroline Zook 2010

We didn’t quite get to celebrate 10 years together in a way we’d thought we would in 2020 (😷) but we did our best. We got to be together and that’s all that really matters.

Zook Anniversary

If you want to relive some of our best memories and stories of the past 10 years, listen to the 10-year look back podcast episode we recorded!

🙏 Our health and Caroline’s improved relationship with her anxiety

You may have noticed we didn’t write a 2019 Year-End Review. That’s mostly due to the fact that 2019 was a really tough year for us and admittedly the toughest year of Caroline’s life thus far due to her struggle with debilitating anxiety.

Sometimes you have to sit in a dog bed

☝️ This is a photo I (Jason👨🏻‍🦲) took one day when Caroline was having an especially rough go in 2019. I am so grateful we haven’t had moments like in 2020 and most of this year has been filled with smiles and laughter.

Jason and Caroline Zook

If you didn’t hear about Caroline’s struggles with anxiety, we talked about it on this podcast episode and she shared a good amount on her Instagram account @ckelso (just scroll back a bit to 2019 posts).

Toward the end of 2019, Caroline was able to come out of an incredibly difficult year 🙌 and it showed us that her mental health is priority #1 in the Zook-household. We cared about mental health before 2019 but now it’s truly the thing we place above all else.

We also want to mention we feel extremely fortunate and privileged that COVID-19 has not directly impacted our lives too much this past year. We took it very seriously from the beginning and will continue to doing everything we can to avoid getting it (or unknowingly passing it on to someone).

👍 Wandering Aimfully (our un-boring coaching business) finally got its footing!

We started Wandering Aimfully (WAIM) back in August of 2018, which feels like three decades ago thanks to 2020.

  • What started as a $100/month Membership Community,
  • Turned back into our Lifetime Membership (like the previous iteration BuyOurFuture),
  • Then became a 6-month Un-Boring Coaching Program,
  • Has now ultimately become our one offer to rule them all: Our WAIM Unlimited Program which brings everything we do together, with live monthly coaching, and a whole lot more!

From a revenue standpoint, our WAIM business started 2020 at $9,400 MRR (Monthly Recurring Revenue) and ended the year at $20,150 MRR.

Wandering Aimfully 2020 Revenue

This year’s monthly revenue took a fantastic jump and we can attribute this to a couple of things…

We honed-in our messaging, specifically who we are for and how we can help them

This may seem SO OBVIOUS but it’s also one of the hardest things to do when you start a new business. We experimented our way through many offerings and many customer-positionings, finally landing on a program that checked all the boxes for our members AND became much easier to explain and sell.

We learned a hybrid-selling model is best for us

When we started WAIM the entire goal was to get more predictable monthly income. For many years we’ve survived using only a launch model (opening and closing the doors at certain times). This model was okay, but it also put a TON of pressure on our launches. In 2020, we were able to finally start to crack the proverbial nut on bringing in some “evergreen” sales of WAIM as well as doing an open enrollment twice throughout the year. This mix of selling tactics put less pressure on ONE launch to succeed.

Adding affiliates was always the plan but we finally were able to make it happen

Of the 183 new WAIM members we added in 2020, 68 of them came from our existing members! That 👏 is 👏 freakin 👏 awesome! We are so happy to have our members bringing new members in because we can almost guarantee they’re going to be a good fit for our WAIM family!

Wandering Aimfully 2020 New Customers

This year, all things considered, we had a lot more fun running WAIM

We can directly attribute this to our Monthly Un-Boring Coaching sessions. They are the thing we spend the most time creating for our members each month but they are also the most rewarding (and enjoyable!) for us personally. Sometimes in business, you can figure out how to increase revenue, but it’s not work you like doing. We are so grateful to have figured out how to boost our revenue AND have more fun with un-boring coaching sessions.

A quick final note about WAIM…

We are SO proud to be part of the amazing WAIM Community. It feels supportive, caring, motivating, and all-around just full of lovely and talented people.

😱 We spent nearly all of 2020 rebranding and redesigning the entire interface for our online course software Teachery

Juggling two businesses is no joke, but it’s even harder when you’re partners in life and partners in business (twice over!)

This year definitely challenged us more than we’ve ever been challenged when it comes to collaborating and working on a large project. We’re happy to report this massive test and the amount of stress we put on our relationship was survived! 🥵

Teachery has been around since 2014 and it has never received the branding and design-love to reflect the amazing customers who use it daily. From a technical standpoint, Teachery isn’t nearly as complicated as some other course applications, but that doesn’t mean it didn’t take HEAPS of work to redesign the entire thing.

Our little course platform went from “blah and zero personality” to “energetic and creative!”

Teachery Before and After 2020

We aren’t exaggerating when we say it took us all of 2020 to finish redoing everything with Teachery. The new version of Teachery went live on December 11, 2020, and we couldn’t be happier with the result!

A HUMUNGOUS shoutout to Caroline for her incredible hard work, amazing design talents, and willingness to teach herself how to be a UI designer (and work with developers!) Also, a big shout out to our development team at Effectus Software for making all the visual changes a reality!

👩🏻‍🦰 Caroline manages processes,👨🏻‍🦲Jason manages projects (and we started using Notion!)

We’ve come to learn that Caroline is the Process Manager and I (Jason) am the Project Manager. While there is definitely some overlap, this working relationship in 2020 has proven to be REALLY successful for us.

When you work with a partner, it helps to have defined roles (much different from defined cinnamon rolls!) For us, we’ve always had some delineation to our roles, but 2020 showed us the processes vs projects separation was super helpful! It helped us work through loads of situations where we finally had someone who was “in charge” and could take the lead (as opposed to two people jockeying for one role… or the last bite of a roll 😬).

2020 also introduced us to Notion! Funny aside, we actually found Notion a few years ago and I completely failed at trying to explain to Caroline on video in 2019 so we never started using it (Notion explanation failure starts at 52:20 mark)…

Caroline gets 100% of the credit for being the Notion-champion in our household. After combing through video after video from Marie Poulin and August Bradley, she brought all of our hacked-together sheets, docs, notes, boards, and lists into ONE APP TO RULE THEM ALL!

This is exactly why the Yearly Planning Notion Template we shared at the beginning of this article is so thorough and helpful. It brings everything you need into one place.

It’s safe to say we’ll be using Notion for 2021 and beyond. It’s replaced Asana, Airtable, Google Sheets, Notes, and a few other applications for us (for a fraction of the total price too!) Well done, Notion. Well done.

Jason Zook Action Zone Notion

🍿 We continued our trend of “Classic Movie Night” on Saturday nights

This is absolutely one of the most fun things we do together as a couple. Every Saturday we queue-up two movies we remember from our childhood (or maybe missed out on), pop some fresh popcorn, and curl up on the couch together.

Some of our favorite movies from 2020:

  • Speed (probably our fave of the 100+ movies we’ve watched)
  • Men In Black (just a gem!)
  • Hard Target (yep, JCVD flick)
  • The Day The Earth Stood Still (underrated!)
  • Waterworld (so bad it’s SO GOOD)
  • The Fugitive (one of 👩🏻‍🦰’s all-time faves)
  • Anaconda (also, so bad it’s gooood)
  • Demolition Man (I had to convince Caroline to watch this and she ended up thoroughly enjoying it)
  • Deep Blue Sea 3 (objectively entertaining!)

This tradition will continue for as long as we have movies to watch from the 80s, 90s, and early 2000s.


What Didn’t Go Well In 2020?

Just a heads-up about this section… We didn’t want to leave out some of the tougher things in 2020, so if reading about COVID-19, Black Lives Matter, or us losing our dog could be triggering for you in any way, feel free to scroll past this section of our review.

🦠 Well, COVID-19, obviously.

Oof. We don’t have to tell you how disruptive having a pandemic happen was.

It’s truly so sad to know so many people lost their lives to this virus in 2020. We don’t want to harp on COVID-19 for much of this review, but we had to acknowledge just how sad and awful it has been.

We did our best to find the silver linings in the world’s collective pause, but we also made space to be understanding with ourselves when work productivity was affected by what was happening in the world.

Here’s hoping vaccines roll out smoothly in 2021 and we can all get back to some sense of normalcy 🤞🤞🤞.

😞 We don’t want to skip over the racial injustices that were highlighted in 2020

A pandemic is hard enough, but 2020 really unearthed another virus that’s been rampant in our culture for hundreds of years.

We watched George Floyd’s murder and like so many other people, it flipped a switch in us. No longer could we sit idly by and not take action (both internally and externally).  We came to understand the difference between being non-racist and being truly anti-racist, and we made a commitment to make anti-racist actions a lifelong priority for us.

We are not going to ask for any praise and we are not looking to share all the work we’ve done and continue to do related to learning about systematic and systemic racism. As two very privileged white people, we are simply trying to do our part to educate ourselves, to be part of change, and to make this a part of our daily lives.

If you want to read more about our public Social Justice Stance you can do that.

We are hopeful that change will happen more rapidly as we collectively become more aware of the disparities our BIPOC friends have to endure each and every day.

🐶 We had to say goodbye to our beloved fur-kid Plaxico 💔

Definitely got dust in my eyes while typing out this section. After 13.5 amazing years with our lovable little Staffordshire Bull Terrier “Plaxico” (Plax) we had to let him take his trip down the rainbow road.

Plaxico The Dog

It’s so hard to lose a pet and neither of us had done it as adults. I picked Plax up from a small farm in Central Florida wayyyy back in December of 2006. I’ll never forget 8-week old puppy Plax running under a shed with a stick and barking at me. He was so full of personality from the very beginning.

We know we gave him a fantastic life and he got to experience so much of our 👩🏻‍🦰👨🏻‍🦲 10 years together.

We feel extreme gratitude that we were able to give him a peaceful goodbye just two weeks before COVID-19 hit in March. The timing, while never good for such a sad thing, couldn’t have been more fortunate.

We miss him every single day but know he lived a fantastic life atop many pillows, dog beds, couch cushions, and even as a “hat” in our bed each night.

Plaxico as a hat

🤖 Our cheeky marketing project “WAIM Exposed” didn’t quite go to plan

Okay, jumping from 😭😭😭 back to business (sorry!) we decided over the summer to try out a WEIRD marketing idea. We just wanted to do something really different and unique (harkening back to my t-shirt wearing, last name selling, silly antics!)

We had an idea to create an audio coaching experience for our WAIM members. If they needed a jolt of inspiration or some on-demand coaching around a feeling they were experiencing, we could record a bunch of short audio clips for them to listen to whenever they wanted. That led us to the silly way to promote this, which, slightly backfired.

After hours of brainstorming, we leaned into Caroline’s LOVE of crime podcasts, thriller movies, anything relating to some mystery and intrigue. Our idea was to put together a 🕵️‍♂️ Conspiracy Website 🕵️ where someone on the internet would be exposing us for not being actual humans, but in fact, being ROBOTS.

We thought this was hilarious.

The website would be an over the top idea that people would see as a silly joke and then check out the audio coaching idea as it related to our WAIM Program we were selling at the time.

WAIM Exposed

Lesson Learned: When people trust you, they REALLY trust you

We “launched” our WAIM Exposed Conspiracy Website to our email list with a very vague email announcement. We mentioned that we’d stumbled across the site, didn’t know who made it, and that they were alleging we were robots. You know, something really outlandish we thought people would scratch their heads at, click through to, and laugh at us knowing it was a joke.

While about 60% of our audience got the joke right away and knew we were behind it, the other 40% did not. 😬😬😬

Uh oh. Immediately we started getting replies that people were angry on our behalf, they couldn’t believe someone would do this, etc. I remember Caroline coming out of our bedroom from a lovely night of slumber, only to find me looking like I’d seen a ghost. We had some work to do!

In the grand scheme of life, it wasn’t a big deal AT ALL (especially with everything else happening in 2020), but, we definitely felt like we learned a big lesson that when people trust you as much as our audience does, we have to be a bit more direct when something is a joke and shouldn’t be taken seriously.

All-in-all, WAIM Exposed was a fun project to work on, we could’ve just done a better job on the explanation and had a little bit LESS conspiracy to it all. 😂


🔮 2021 Preview (What’s Next?)

🦄 WAIM: Continued monthly un-boring coaching

We’ll be doing monthly un-boring coaching for our WAIM members throughout all of 2021.

We also want to create some fun new things for our members (like we did with the Audio Coaching and the Un-Boring Business Roadmap this year). We have NO IDEA what those things will be in 2021, but we’re carving out space and time for them.

We’d also love to improve our “passive funnel” for selling WAIM along with our bi-annual (Spring and Fall) open enrollments. There isn’t a specific revenue goal, except for keeping up with MRR as current members finish their payments.

🍎 Teachery: The biggest opportunity for growth!

Now that we have a brand new look and feel for Teachery, we’re extremely motivated to work on it. What does that mean exactly? We’re not 100% sure, but we do have a few ideas on our shortlist:

  • A newer, more modern course template
  • More automation and upselling features
  • Some fun marketing efforts (which we’ve never done for Teachery before as it’s grown 100% because of word-of-mouth)
  • Customer interviews and conversations
  • Trial membership tweaks and improvements
  • Robust in-app education

From a revenue standpoint, Teachery currently makes ~$10,000 MRR and we believe we can double that number in 2021 without overworking ourselves. We shall see!

🤔 A passive income project around Squarespace?

We’ve been trying for years to create a truly passive income project and we have a solid idea for one but we simply need the time to work on it.

If we can make it happen (without added stress), we hope to share this journey with you as we want to start completely from SCRATCH. No audience. No email list. Just an idea and our Un-Boring Business Roadmap to help lead the way.

More on this in 2021, hopefully!

🙅✈️ We were going to move to Europe in 2021, that’s most likely 2022

It’s been on our life bucket list for many years to move to Europe for a year. That was supposed to kick off in Spring 2021 but for obvious reasons (🦠) that’s not happening.

For now, our tentative plan is Spring 2022 for our year in Europe. However, if vaccines roll out smoothly and we feel safe enough, we could move that timeline up to the end of 2021. We’ll just have to see how it goes.

We’re not asking for any sympathy that our Europe plans got derailed. We know we’re in an incredibly privileged place to even be able to make that dream come true. If it happens for us, we’re super excited. If not, we’ll be just fine and we can travel later in life when it’s safe 🤗.

👫 We hope to continue the daily laughter, love, and enjoying life together

It’s easy to only share the highlight reel of a relationship in emails, social media, and articles like this. But, just know we have a fair share of disagreements and skirmishes (especially when redesigning a software application 😂🤪).

But, we are always working on our relationship together. We’re always trying to be better for each other and to support one another.

2021 will be no different in that regard, we just hope we can do an even better job of listening to one another, caring for each other, and laughing at all the silly antics we get into.


Let’s Wrap It Up! How Are We Framing 2021?

Each year we pick a word that helps us frame the next year. The word becomes a mantra and we’ve done this since 2015 (it’s super helpful!)

Caroline’s word for 2021: Spark

Since all of my health struggles in 2019, I feel like my focus has really been on my internal world. I’ve worked hard on my mindset, healing traumas, reprogramming negative thought patterns, and trying to stay in the present moment. But inside all that reflection, I haven’t done that much creating. At least, not in the way I used to. I feel ready to welcome expression, creativity and exploration back into my life now that I feel safer and more at home in my own skin. I don’t know what that will look like yet, but I want to remind myself to follow that “spark” of inspiration and look for it in all that I do. I want to encourage myself to invite in that sense of vitality and energy and curiosity when I can.

Jason’s word for 2021: Optimism

I feel like I do a pretty good job of being optimistic when it comes to our businesses, but just about everything else in life I tend to lean toward pessimism. 2020 has given me lots of opportunities to learn how to lead with optimism, yet I know I certainly didn’t think that way. I’d like to focus on being more optimistic next year and (possibly) think kinder thoughts before jumping toward negative conclusions.

Are you writing a “Year-End Review”? We’d love to read it!

If you decide to write your own Year-End Review post feel free to send it to us via email (head to our contact page).

We hope you enjoyed reading our review! 👋👋👋

050 – We Scrapped Part Of Our Big Launch, The Uncertain Times – Ep 10

May 28, 2020

Listen to the audio version

Episode Summary

Whenever you’re doing a launch for a product you typically have multiple ideas and plans. For us, we had ONE specific plan that involved something way more hands-on and a ton of extra effort (YouTube Live, promotion, etc). We decided to completely scrap 🙅🏻‍♀️🙅🏻‍♂️ that part of our launch plan to keep our sanity.

If you run your own business or are selling anything, it IS important to make money to be sustainable but *not at all costs.* This is why you put a plan in place well ahead of time and you can adjust on the fly as needed – like we did this week!

We spent some time talking about 👀SALES FUNNELS 👀 and how we’re rethinking these for our own businesses. The subtle reframing to 🌉MARKETING BRIDGES 🌉should help us not get bogged down with negative thoughts about selling, as that even happens to us. Sales funnels/marketing bridges ARE essential to running efficient online businesses and they don’t have to feel gross or sleazy.

We also shouted out more of our new WAIM Coaching members and even included some silly made-up facts about them. #fakeshoutouts

🗣 Leave a comment on YouTube: Are you a “🌺 delicate flower sleeper” or a “🤖 robot sleeper?”



If you’re looking for (un-boring) business coaching to help you grow your business, gain more free time, and have more fun, join our 6-Month Group Coaching program. You can get your first month for 50% OFF if you use the code casper at checkout!

Joining Wandering Aimfully is the best way to help support us on our journey AND help yourself grow your business with intention and on your own terms.

049 – If You’re Not Enjoying Your Business, Switch It Up – The Uncertain Times – Ep 9

May 21, 2020

Listen to the audio version

Episode Summary

One of the things we wish more online business owners understood was how important experimentation is AND how long it can take until you find your footing.

Yes, we ALLLL want success to come to us faster but it doesn’t happen just because you dream about it. For our own Wandering Aimfully business, we’ve tried tons of stuff in the past two years. If you want to read about all our experiments, what’s worked, what hasn’t, and how we’ve dealt with all the bumps along the road, go here.

If you’re feeling in a bit of a rut or you haven’t seen much movement with your biz lately, maybe it’s time to SWITCH 👀 IT 👀 UP 👀. Doing something new can reinvigorate you and whatever part of your business you’re working on (as we shared with a WAIMer Michelle!)

Big shoutout to the new WAIM members joining us during our final enrollment period of our Un-Boring Group Coaching program this month! We’re stoked to have so many new faces! 😍

🗣 Leave a comment on YouTube: What routines, content strategies, habits, etc, do you need to switch up with your biz after watching this episode?



If you’re looking for (un-boring) business coaching to help you grow your business, gain more free time, and have more fun, join our 6-Month Group Coaching program. You can get your first month for 50% OFF if you use the code casper at checkout!

Joining Wandering Aimfully is the best way to help support us on our journey AND help yourself grow your business with intention and on your own terms.