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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

😍 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

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!

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! 👋👋👋

Why You Should Focus on Enough Instead of More

February 8, 2020

There’s a culture of more going on right now. More money. More social media followers. More customers. More attention. More. More. More. Instead of focusing on more, we’re focusing on enough.

Raise your hand if you’ve recently felt yourself falling into the trappings of more:

  • You’re trying to grow your business, so you’re doing more marketing, more sales, more content creation, maybe even thinking about hiring people
  • You have a big ambitious financial goal and you are pretty far from it right now
  • Your schedule is packed to the brim leaving no white space in your life
  • You constantly feel overwhelmed by all the things you can/want to do, but yet you feel like you’re never actually getting things done

We don’t bring these things up to make you feel bad about yourself or your choices, we bring them up because we’ve fallen prey to these ideals over the years.

Take a moment and ask yourself this simple question:

Are the goals and dreams I’m striving for my own or are they things I’m being told I SHOULD want?

That’s a powerful question to answer honestly, and one we took a really hard look at a few years ago when we found ourselves feeling overworked, overwhelmed, constantly stressed out, and even a tinge of shame for not being as “successful” as our peers.

Oh, hello by the way! We’re Caroline and Jason Zook 👩🏻‍🦰👨🏻‍🦲👋, a husband and wife duo that runs this Wandering Aimfully website. We don’t always introduce ourselves mid-article but this one felt appropriate because this conversation about enough is soooo important to us. We wanted you to know who “us” was.

Jason and Caroline Zook Sunset Beach

(This is a well-posed photo of us doing one of our favorite free activities in the world: staring out into the ocean – even though we don’t live in an ocean-front home because that would cost too much and would compromise our values of “enough.”)


It’s time to stop feeling overwhelmed and stressed out, and that starts by embracing the idea of enough.

The societal pressures are real. The perfect lives we see on social media are consuming our feeds. Taking huge risks and “going for it all” are things that are praised and applauded, even though the true outcomes of what those things lead to are rarely shared.

Let’s slow down and shift from more… to enough.


What Is The “Enough Mindset” And Why Should You Embrace It?

Plain and simple, the way we define the “enough mindset” is:

Clearly defining your own limitations in life and business that YOU feel confident, comfortable, and happy with.

Many years ago, I (Jason) wanted to own a $1,000,000 per year revenue-generating business. While I didn’t actually achieve that goal, I got fairly close ($600k) and it was the worst year of my entrepreneurial life. I had to hire employees. I had to spend every waking hour chasing after more customers. My business expenses went through the roof. I was working 14-16 hour days with zero time allocated for taking care of my physical or mental health. I ended up burned out, in debt, and miserable.

Are you in the same boat I was a few years ago, working yourself to the bone? If you’re reading this article and you feel like you’re burning the candle at both ends then the “enough mindset” is something we believe you need immediately.

Maybe you’re not like I was a few years ago BUT everything you see around you feels like too much? Everyone you follow on social media is going after super-ambitious goals. The people you work with or surround yourself with have huge ostentatious dreams. You feel tired just thinking about what it might take to be “successful.”

We’re not saying you shouldn’t have big dreams or big goals.

The key to the enough mindset is defining your upper limit.

We have big dreams and big goals (we’ll share more of those below) and we want you to have your own bucket list too. The key, though, is to have YOUR big dreams and YOUR big goals.

Just because having a business that makes $1,000,000 sounds cool doesn’t mean it’s right for your life and your situation. Just because living in a beachfront home looks luxurious doesn’t mean it’s a good plan for you and your family. Just because other people want to have a bunch of employees and be doing all the things doesn’t mean you need to follow in their footsteps.

One of the most common dreams we see in the online business space is “making $100,000 per month” or “having a 6-figure launch of a product.” The problem with these types of dreams or goals is that most often they aren’t accompanied by the big fat list of caveats:

  • You will have to hire people to help you. (How do you find good people? How much do you pay them? Can you afford to pay them for years beyond one launch or one amazing month?)
  • You will have to spend money to make money. (Do you have money to invest in the tools it takes to generate more money? Can you afford to spend money on paid ads? Have you looked at how your expenses will grow as revenue grows?)
  • You will have to work more hours than you do now. (How many hours do you work now to make the money you currently make? Do you have enough time for friends and family now?)
  • You will have to learn a lot more than you know now. (Do you like learning new things? Do new technical challenges scare you or excite you? When new things go wrong how do you handle them?)

That list of caveats could go on and on, yet when people sell you the dream of making a lot of money they don’t tell you all of those things; you wouldn’t buy their slick product or service if they did.

Nowadays we use the simple mantra “Grow Slow.” We DO want growth in our business revenue but not at break-neck speed and not at a pace we can’t control.

There's nothing wrong with growing slow

We hope you’re on the same page with us about the problem of more and ready to embrace enough. Let’s break down exactly how to do that…


How To Define Enough For Your Life And Your Business

Let’s get to the good stuff! Let’s dig into how to define your enough because enough is subjective to each and every person. Our enough may be wildly different from your enough, and that’s okay!

We don’t want this article to only focus on money but as well know money is a huge part of our lives. So let’s get the money convo out of the way and then we can move on to other things.

💰 Defining Enough: Start with your MMM Number and then establish your Enough Number

Your MMM Number is your Monthly Minimum Magic Number. This is the bare minimum amount of money you need to make ends meet for your current situation. Too often a baseline isn’t set when it comes to money and that’s why we all chase more, more, more of it. And trust us, we don’t want you to live off the minimum amount of money you need forever, but you have to START with that number.

The MMM Number formula:

  • Minimum monthly living expenses
  • + Minimum monthly business expenses
  • + Paying off debt (monthly payments)
  • + Peace of mind cushion (monthly savings)
  • = Your MMM Number

You should be surprised at how low that number is compared to the bigger numbers you’ve been thinking about. Again, this number is great because it’s setting the minimum you know you need to live your life, provide for your family, pay down debt, etc.

Now that you have your MMM Number it’s time to establish your Enough Number. The super-important key to your Enough Number is to pick a realistic number you want to grow to based on your current MMM number. Think of your Enough Number like the next mountain you want to climb but one that doesn’t have a mountain after it. The second (enough) mountain is your ceiling. It’s your cap. It’s your line in the sand to avoid chasing more more more.

MMM Number and Enough Number

The Enough Number formula:

  • Your MMM Number
  • + Realistic monthly revenue growth in your business
  • + Additional money you want to save/invest each month
  • = Your Enough Number

What is YOUR Enough Number for your current situation? Is it less than you may have been shooting for these past months or years? It should be! And, establishing your Enough Number should feel empowering because it’s a number you can actually achieve based on your true goals and values.

IMPORTANT: If/when you hit your Enough Number, you can stop growing. You can slow way down. You can embrace the fact that you made it to the top of your (enough) mountain and didn’t sacrifice your sanity to get there. This is a beautiful place to be in life and we should all strive to feel this sense of “success.”

🖥 Defining Enough: What level of quality in your work is good enough?

When it comes to working, it’s very easy to slip into bad habits of overwork and perfectionism. It’s not uncommon to find yourself still working many hours past what you estimated you’d work. It’s also not uncommon to be toiling away trying to perfect every last piece of what you’re working on, only to realize you’re staying stuck in the details.

We are recovering (and 100% truth: sometimes still) perfectionists. We’ve been known to spend too much time on the smallest, most minute part of a project, then wonder why we missed our own deadlines. Over the years we’ve gotten much better at avoiding perfectionism and overworking by spending our working time in the “enough space” of work. This diagram Caroline created sums this up perfectly:

Defining Your Enough Space

Low quality work won’t cut it. It should be obvious that we’re not advocating to publish/upload/launch/release crappy stuff.

Super high-quality work can be dangerous. Quality is VERY important to us but we also know it’s a slippery slope. One way we’ve learned to combat getting stuck focusing on super high-quality is to publish/upload/launch/release what we’re working on in a “good enough” state of completion. Then, let our customers tell us if we missed the mark somewhere.

It can feel weird to put work out into the world that you know isn’t as perfect as it could be. But, perfection is subjective, and if you’re the type of person that focuses on perfection, your good enough will absolutely get the job done.

⏳ Defining Enough: How much margin do you want in your life?

THIS. This is a very important part of the enough conversation. You can interchange the word “margin” with white space, free time, downtime, etc.

It’s rare that we actually plan for space in our lives. It’s rare that we prioritize having an abundance of time. Yet, isn’t all the time and energy we spend working for a goal of… not working in the future?

We like to ask ourselves this question often: What is it all for anyway?

  • What are the countless working hours for?
  • What is all the stress for?
  • What is striving for some gigantic goal for if it leads you to have zero margins in your life for what actually matters?

Are you the type of person that needs a slower start to your day? Then you need to build morning margins into your schedule.

Are you the type of person that needs more savings? Then you need profit margin and minimizing expenses is huge for you.

Are you the type of person who gets overwhelmed easily and needs frequent breaks? That’s OKAY. That’s not a weakness. It simply means throughout your day you need to prioritize breaks, self-care moments, etc.

Margin and free time should not be luxuries we earn at the end of our lives. They are things we should build into our lives right now.


How We’re Using The Enough Mindset In Our Businesses And Lives

Now that we’ve gone through the idea of enough, our enough mindset, and helped you define what enough might look like in a few major aspects of your life, we want to share some changes we’ve made in our lives.

These enough mindset changes help keep us sane. They help us avoid perfectionism. They are values we hold to avoid the trappings of societal pressures.

We want enough money to live a comfortable life.

We don’t want all the problems that come along with trying to make more money. We don’t want money to control our decisions ever again. We don’t want the pursuit of making more money to be any kind of driving force in our lives again. We don’t want all the additional expenses that come with generating additional income.

We want enough money to know our bills are paid and that we’re building up our savings.

We want enough of an audience we can actually manage.

We’re not interested in being famous or amassing some huge following. I’ve (Jason) had an incredibly small slice of what that feels like, and it’s completely overwhelming. I remember having an insurmountable amount of emails (400-500 per day) to reply to, and it’s not fun—especially when you genuinely care about replying to people.

We don’t want so many social media followers that we can’t keep up with comments and DMs (we love those conversations and cherish them!) We don’t want so many email subscribers that we can’t reply to everyone who takes the time to write to us. We don’t want server-crushing traffic to this website, we want the RIGHT, manageable amount of people coming to our site.

We want to be able to reach enough people that we feel reachable in return to those people.

We want to go on adventures at our own pace.

We love simple adventures. We enjoy a short road trip. We look forward to tropical vacations that take a 2-hour flight and where going through customs is a breeze. We like one or two bigger, more meaningful trips every year that take us to a new destination. But you better believe we’re going to research the heck out of that place!

Zooks go to Iceland

A few years ago we went to Iceland and saw just enough waterfalls. We didn’t try to cram in EVERY spot people told us we should see. We traveled on our own terms and loved (almost – that’s a story for another post) every minute of it!

One of our big goals in life is to live abroad for a year (or more). But, we aren’t going to be the type of travelers who live out of backpacks and are on the move every week. That’s too much for us. It would stress us the heck out. Instead, we’re going to pick one city per month and create a home base. We may take short trips here and there while in that city, but we’re not van-lifers and we’re not trying to become full-time nomads.

We want enough friends, but not too many.

There was a time when the number of friends we had mattered. It was a quantity game. A badge of honor to have so many names in your phone’s address book that multiple finger swipes didn’t even get you through the last name’s that started with “A.”

These days though, we don’t want to have to make tough decisions if two friends are having a momentous life event on the same weekend. We don’t want too many friends pulling us in too many directions, leading us to the guilt of having to say “no” (or worse, showing up for things we don’t actually want to be doing).

We want enough friends that we feel we can make an impact on their lives, and they on ours. We want enough friends that we can actually remember all their birthdays (even though we still forget because being a human is hard).

We want enough time, but not too much.

Our minds can be a swirling mess and we know we have to take breaks from our work. Yet, we know we’re not the type of people who can sit on a beach for two weeks and do nothing. One of us gets completely bored within the first 36 hours 👨🏻‍🦲.

We want enough time to enjoy the limitations of time. We like constraints and limitations on our time because it helps us feel empowered that we only have a certain amount of time to accomplish a task or launch a project. Having just enough time can make the time you have that much sweeter.

We want enough projects to keep our minds busy.

A few years ago we had too many active projects going on. We had too many self-imposed deadlines, customer groups, domains, and all the other things that come along with too much work. We spent six months talking to each other about paring down our projects and combining our separate business and audiences into one entity (Wandering Aimfully).

I (Jason) sold off three separate software projects I was working on. I had fallen into the trappings of more simply by chasing my own ideas and dreams. Our brains have no issues coming up with new ideas but our brains aren’t forward-thinking enough to know the trouble juggling too many projects can get us into. We’ve drawn our line in the sand for this current season of our lives and we’re running two projects only: Wandering Aimfully and Teachery. That’s it.

We still want to be learning and diversifying our skills but we want to do it at a slower pace than most people.

We want enough customers, but not too many that we have to hire people.

Some business owners take pride in immediately outsourcing things or hiring people to handle design, development and customer service. Especially when it comes to customer service, we want people to feel treated exactly how we’d want to be treated. We know the value of connection with our customers and how much it means to them to hear from us (and we like the same thing from the businesses, products, and services we pay for).

We want enough customers that we can always reply to questions. We want enough customers that we have the ability to not get overwhelmed when something goes wrong. We want enough customers so that when our competition keeps playing the game of more, we can stay right in our lane of enough.

We want enough people reading this to understand that when we say, “We’ve made it,” we’re not being arrogant or gloating.

We’ve worked really hard to get where we are in our lives right now. We’ve put in countless hours of hard work, both in business and in our relationship. We’ve dug deep to figure out what we really value in life and how not to get caught up in what society tells us we should value. We’ve had conversations with fellow entrepreneurs who go silent when we tell them, “We’ve made it”—both because we think they’re shocked to hear someone actually say that, and because their version of enough is measured by more, which has no end in sight.

We want enough people reading this to understand our definition of “making it” might be wildly different than yours as long as it is YOUR definition.


We Want You To Focus On Enough

More is a losing sum game. Once you get more, you only continue to want more. We’re pre-wired this way. Human beings instinctively collect more because thousands of years ago we had to if we wanted to survive. The things we have the ability to collect have changed, but our instinctual habits to collect things have not.

👉 It’s time to define your enough.

👉 It’s time to create more margin in your life instead of filling every moment with work.

👉 It’s time to embrace the fact that you may need way less (of everything) than you think you do to be happy.

It’s time to draw your line in the sand and realize you’ve been on a path that isn’t congruent with who you actually are or what you really want in your life.

We hope this article helps you make an important shift in your life, a shift away from constantly striving for more to striving for enough. 

038 – Our Weirdest and Most Helpful Rituals

July 17, 2019

Listen to the audio version

Episode Summary

Rituals That Make Our Lives Better
When it comes to weird rituals, we have a bunch! As weird as some of our daily rituals are, they are also some of the most helpful things we do to stay grounded and productive.

One of Jason’s weird rituals has gone on for over 1,000 (nearly) straight days and it took him from feeling negative throughout each day to creating a ripple effect of positivity as soon as he opened his eyes each morning.

Caroline’s most important rituals have evolved over the past six months as she’s been willing to try any new habits to overcome her bout with anxiety. Her latest morning ritual has been extremely beneficial!

Have a listen as we chat about the rituals we’ve created, the habits we’ve formed, and how we think about making positive changes in our daily lives.

🤔 QUESTION FOR YOU: What are your weirdest or most helpful rituals? Also, do you like the banter of these episodes or the topics we dive into? (Feel free to comment with your answer on YouTube).


👉 New Project Alert! 👈

We’ve cooked up something new called Building A Squarespace Site from Start to Finish or “BASSSF” (as Jason loves to say). You can follow along weekly as we build a brand and website from scratch then sell the entire thing in a unique way. Should be a fun project for the next few weeks!


Want to support us and our show?
Wandering Aimfully Memberships

We recently created a 100% free, no strings attached Test Drive of our Wandering Aimfully Membership. You can kick the tires and see all the goodies we have to offer, along with a hands-on preview of our newest program Build Without Burnout Academy (a 6-month guided program to help client-based business owners transition to digital products).

You’ll also be able to see inside our “Vault,” which contains 30+ courses and workshops to help you grow your business or make big changes in your life. Give the WAIM Test Drive a shot and don’t hesitate to reach out and set up a quick 1-on-1 call with us!

Joining Wandering Aimfully is the best way to help support us on our journey AND help yourself grow your business (or start a business) with intention and on your own terms.

Community Post: 6-Month Goals From Wandering Aimfully Readers

March 17, 2019

One of the things we value most about Wandering Aimfully is the amazing community of creative folks we get to interact with (that’s you!)

However, because we don’t have comments on articles and we aren’t always active on social media, there isn’t a great way for you to meet or hear from your fellow creative peeps.

That’s why we decided to ask in a recent email for our subscribers to reply with the answer to a simple question: What is your biggest business/life goal in the next 6 months?

Our hope in sharing the replies we received that it does a handful of things:

  • 👋 Introduces you to some other Wandering Aimfully peeps
  • 👌🏻 Gives you some context on your own 6-month goals
  • 🤩 Inspires you to take action in your own life
  • 😎 Confirms that you’re in a community with like-minded creatives

Without further ado, we hope you enjoy reading through the goals of other community members…

My business goals for the next 6 months: Have a consistent load of 5-8 coaching clients and have booked 6 workshops (1/month – this is a stretch, but what the hell!)
– Elizabeth Treccase

My business goal for the next six months: FINISH THIS DAMN BOOK REVISION. I’ve been working on it for the last three years, through bouts of (f)unemployment and paralyzing depression (maybe you can relate), but I really believe in this book. It’s fiction, set slightly in the future, and climate change is a major plot point, so it seems especially relevant now. I’m close to done; my immediate task is setting up some consistent, achievable goals to get to the end.
– Jeff Ricker

Figure out how to incorporate my recently acquired full-stack software development skills into offerings for my clients. Now that I can build more sophisticated, data-driven, web projects, how do I put that to use? What needs can I fill for outdoor industry companies while remaining independent?
– Carrie Carter

My goal for the next 6 months is to make $20k to pay for college next year.
– Maya Sparks

The big goal in the next six months is to take the half done things and spin them up. 1. The general explanation of the things I’ve done over the past 15+ years on the internet. 2. Spinning out into a standalone product and making that something I can run marketing against to try and get that to $1K/month recurring. 3. Seeing the initial results from the domain flipping process (went live yesterday) that leverages the NameSpacery technology. If that’s a go, continuing to do flipping but also making further investment in the SaaS model. 4. Taking my ancient Udemy course on social media crisis management, updating it and spinning that up on Teachery to be its own standalone product under the old brand
– Kade Dworkin

Replace my current income from my main marketing client with income 100% from my new coaching business.
– Miles Hanson

My business goal for the next 6 months is to get my life in order. We’ve been lucky enough to see some decent growth in our business but it’s requiring extra time and attention on my end. I am in a season of life where I do not have the ability to work tons of hours like I used to (due to some family things that will not likely change for at least a year or two). I essentially need to work on efficiency, prioritization, issue capture and reflection, todo management, customer expectation management, staying in communication with customers without being resentful of them when they take advantage of access with me (so like finding ways to structure or at least facilitate customer meetings in a manner that allows them to feel like they are getting something out of it without major scope creep). In closing, I am trying to basically become a better all-around person and business person in 3/4 to 1/2 the amount of time I’m used to spending doing less of this stuff 😱. To be realistic and honest I just want to make progress on this, there obviously isn’t a finish line here, just want to chip away and grow (but its also imperative that I do get better or we are going to have some pissed off customers).
– Jeff DeBolt

I am looking to grow my YouTube channel from 19 to 1000 subscribers by September 4, 2019.
– Craig (Coach Gunny) Gunn

My goals for the next 6 months: 1. Finally release Sketchbook Scientist (so many delays!) in March. 2. Get to 500 subscribers on my newsletter (I’m currently at 100+). 3. Remain consistent with my weekly newsletter + weekly content (alternating video and blogposts). I’ve decided not to have a lot of BIG goals because I get so easily overwhelmed. I’ve noticed that I do better by focusing on small goals that I can do easily and quickly (that lead up to a bigger goal).
– Pam Llaguno

My business goal for the next six months is to provide massive value in the form of running a free group every single month and pouring into it as much value as my paid group receives. I want to reframe my business from feeling tons of pressure to sell subscriptions to feeling like I’m providing massive value to people up front and allowing a clear avenue for people who that value resonates with to transition to working with me in a daily manner instead of just once per month. I truly want to love people where they are and honor if they’re not quite ready to take the next step instead of feeling like there is something wrong with how I explained the product or service. That looks like clearing two weekends per month to sharing about this opportunity to generate leads. 1.5 weeks of giving massive value in the group (regardless of actual number of people in it) and 2 weeks of loving & serving my existing clients. I think this will help me find balance between onboarding new members, building trust, & serving those who already trust me without burning out.
– Dr. Lauren Frauenheim

In 6 months, I dream of consistently hitting 10k+ months and streamlining things behind the scenes of my business 💪🏻
– Kelly McElroy

My 6 month goal is to double my freelance income, blog consistently on a weekly basis and grow my email list by 250 subscribers.
– Jess Brown

To be settled on “enough” for our small company, so our family could make the move from driving distance from the beach to walking distance from the beach.
– Russ Cantu

Goal is to replace our current service-based income with digital product income so that we can have more freedom to create fun vlogs, a podcast, and new content for our own business instead of spending all of our time with our clients.
– Lexi Smith

Book $50K in my pipeline within the next six months with new digital products, services, and client work in a balanced and inspiring way that gives me the capacity to head off sailing for half the summer, and hiking and cycling for half the fall. You know, like a boss.
– Chantal Ireland

I’m an illustrator and designer who just switched from client work to products in January. My goal by the end of the year is to have a flea/craft market booth and also sell out of my product. So my goals for the next six months: 1. register for a market, and 2. sell 50% of my current inventory, aka 72 pieces.
– Becky P

Create content consistently + grow my monthly income to my first ‘enough’ number. That means: creating freebies, writing more content for my blog + newsletter fam, [finally] releasing my mini courses + other digital products, and also growing the ongoing services side of my business.
– Rachel Shillcock

Launch my website, consistently create content that makes me laugh, get 100 people on my email list, experience the meaning of life, & disprove the ‘many worlds’ wave/particle quantum theory (because it’s just ridiculous and I for one, believe in accountability).
– Jeremy “Thor” Smith

My goal is to use the WAIM Build without Burnout program to build a productized version of the website design services that I offer, specifically designed for artists.
– Nikki May

Get the website live and offering for sale “Mad-style toast templates” (which were originally suggested to me by a pair of creative entrepreneurs on the west coast 🤠), as well as personal consulting on wedding toasts (I will help you write for $XX offerings).
– Pete Honsberger

Business goal for next 6 months: rebrand and launch as a small team vs freelancer. Secondary goal would be to have 6 months of runway (never had even one month haha).
– Edward Danilyuk

Build up my fun business to the point where I can go down to part time at my “blah” job.
– Chloe Donile

In the next six months I want to grow as a designer and nail some UI/UX/web clients. Furthermore, I want to spend more time creating instead of consuming (which I tend to do too much nowadays). So taking action in my side job to create more, learn more, grow and find web design clients with a cool project that I can do from start to finish using my newly acquired skills (Webflow ftw).
– Mario Moris

Less time working without a dip in revenue. (Ambitious!) How? Finally diversify my income streams. I love my high-end, 1:1 offerings in my service-based business, but with a nearly 4-month old daughter, the desire to work 40-60 hour weeks has quickly weaned. I’d like to continue partnering with 1-2 awesome clients on conversion copy at a time while focusing on leveraging my thought leadership to introduce alternate income streams.
– Sara Frandina

Get out of personal debt.
– Justin Kofoed

1. Publish 300 pieces of media (100 Days of SEO). 100 videos, 100 podcast episodes, and 100 blog posts. 2. Help my course’s founding members (80 of them) become success stories with direct feedback, gather testimonials, and produce at least 3 STRONG case studies from student successes. 3. In month 6, my goal is to launch my course, SEO for the Rest of Us, again. 🙂
– Brendan Hufford

Okay, my business goal for the next month is to start to build an online product that I can sell to replace some client income. I would love to replace $1000 of client income with a product I make to help people. Based on some information gleaned from members of WAIM and people I’ve met in real life, I would love to do a course or email series on discovering and cultivating your personal style to build a wardrobe you love. This is something a ton of people seem to struggle with and I’ve done a lot of work around it to define & build my own perfect style.
– Rachel Lang

Make most of my money from a combination of writing and digital products. (Ambition, whoop whoop!)
– Amelia Eikli

Launch Lights Camera Lawsuit online course.
– Ruth Carter

My goal for the next 6 months is to start and build a podcast that sends an additional 5k unique visitors (minimum) to our site each month without any ad spend.
– Chris Scott

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Why Focusing On Achievement Won’t Lead To Sustained Happiness

August 10, 2018

Below is a little illustration I posted to Instagram, which many of you (as in like… DOZENS of you) commented on with a collective AMEN and I figured that served as an indication to me that this topic might be one worth going deeper on. When I posted this image, I remember the exact state I was in, and maybe it’s one you can relate to it.

Just a few moments before I had realized I was feeling uncharacteristically tired (typically an indicator something is out of sync), so I took a second out of my day to ask WHY? (High five for recognizing my own indicators that something is off; Double five for getting curious about it!)

Without realizing it, over the previous few weeks I had let myself drift back into an exhausting state of “success chasing.”

“Success chasing” is what I call the state where I’m fueled more by my desire for external validation than I am by my satisfaction with internal validation.

How we traditionally define success as a culture

When we think of someone “successful” what attributes immediately spring to mind?

A person who is has name recognition perhaps, whose work is visible on a larger scale than most. Someone who makes good money, maybe has a fancy title, has accumulated accolades or milestones that are recognized as metrics of achievement.

But that’s the thing… all of those attributes have to do with sources of external validation.

External validation vs. Internal validation

External validation is validation that comes from outside of us. It’s a feeling of satisfaction that is dependent upon the opinions of other people. It’s when other people say they like us, or other people offer us accolades and acknowledge them, or when other people see we’re financially well off.

External validation is our default setting because we are humans and we’re wired for belonging. Our culture teaches us that a great way to belong is through traditional paths of success.

But, external validation is a fickle beast. If your happiness or sense of contentment relies on the opinions of other people, you’re entrusting your happiness to someone other than yourself—and that’s a risky move.

Internal validation, on the other hand, puts the control back in your own hands. Internal validation comes from within us. It’s a satisfaction that doesn’t rely on the opinions of other people, only the opinion of ourselves. For me, internal validation comes from recognizing that my actions match my values, plain and simple.

“For me, internal validation comes from recognizing that my actions match my values, plain and simple.”

Therefore, that is my definition of success: making sure my actions are in alignment with my values.

Success based on external validation stems from a place of lacking

External validation is a hole that can never filled. When we reach a milestone and get a pat on the back from our peers, it’s not as though we stop craving that feeling of success. Instead, we keep chasing the next opportunity to feel that way. Hence, “success chasing.”

Success chasing is where the driving force behind our decisions, productivity, and general output comes from wanting to achieve something or be recognized for something rather than the pure satisfaction of creative expression within my core self.

Now the trickiest part of success chasing is that it often disguises itself as motivation. And motivation feels like a very good thing—it fuels us to go after our goals.

The problem, though, is when motivation is coming from a place of lacking—the distance between ourselves and that external validation we crave.

We see what we want. We realize we don’t have it. We work hard to get it. Right? Well unfortunately that particular line of logic also means that our work is stemming from what we don’t have.

The world around us not only feeds us messages reminding us of what we don’t have, but it also makes it pretty clear there are a few traditional things we should have: million dollar businesses, big girlboss-y teams to nurture, and a rapidly growing fan base.

But… there is an alternative based on internal validation instead.

Pursuing success based on internal validation

There’s another kind of fuel that actually comes from internal validation instead. It comes from recognizing not what you want to achieve but how you want to feel. Not what you want the outcome to be, but what you want the process to be.

Instead of success chasing, it’s what I call creative satisfaction (satisfaction as in fulfillment, literally the opposite of lacking.) It’s that feeling that you’re designing your life in a way that’s deeply aligned with your values. It’s a fullness; an integration.

And that feeling creates its own kind of fuel, a different kind of propulsion that isn’t rooted in a sense of lacking or deficiency. Instead it’s one that’s rooted in abundance—an overflowing sense of joy, authenticity confidence.

Here’s a little diagram to show you the difference as it sits in my head (I’m a sucker for diagrams!):

Using alignment to redefine the pursuit of success

In our culture, we often label the external validation framework as the one that outlines the path to “success.”

Why? Because it’s the one we can see.

It’s the one that gives us things we can measure like money and followers and best-selling books and website traffic.

The other framework is much more personal and intangible. Oftentimes, the only one who can even identify it or quantify it is the person engaging in it.

But is there any reason that the second diagram shouldn’t still be a perfectly acceptable framework for success?

In fact, most of us would probably agree that out of the two, it’s the only one that’s really sustainable.

Again, in the traditional version, the joke is actually on us because we never actually catch up to that nebulous benchmark of external validation. We experience tiny milestones along the way, but without cultivating a practice of appreciation, we end up staying in that “hungry” state, resulting in an excruciatingly endless hunt.

And the other framework? Well that’s the one I finally came around to with my revised definition of success in that first illustration.

I found my way back to it by reminding myself that every Monday morning I wake up with equal amounts of peace and excitement. No dread, no expectations hanging over my head, no orders to follow. I’ve reached a point in my professional life where I thankfully control every facet of how I run my business, and that includes NOT waking up on Mondays in a frenzy. It also includes making things I love, that I’m proud of, and answering ultimately to my intuition.

As a sensitive and creative soul who values flexibility, that is my ideal. That is living life in alignment with my values.

What could be more successful than carving out a life for yourself that allows you to live your values daily?

“What could be more successful than carving out a life for yourself that allows you to live your values daily?”

When success is framed as alignment, there’s room for us all

Another reason to shift our success metric from achievement to alignment is because it removes the need to constantly compare ourselves to others.

Throughout my career, there have been several times when self-doubt has crept in my head as I’ve seen someone doing something similar to my work and the question has popped into my head:

Is there even ROOM for me here?

Is there even room for one more personal growth blog?
Is there even room for one more acrylic abstract artist?
Is there even room for one more online business in a sea of so many?

Have you asked yourself a version of this too? My guess is you have because this is a cunning way for our Fear to stop us from ever trying or pursuing the projects that call to us. “There’s already so many ____________ out there, why should I even bother.” That’s a convenient way for us to excuse ourselves from making things or taking a risk, isn’t it?

But it’s a question born out of a scarcity mentality about how the world works. What does this idea of ROOM mean anyway? It assumes that there is one Table of Valid Successful People and that there is a finite number of chairs around that table.

But that’s kind of BS, right? Life is not a zero sum game. There is no such table, and there certainly isn’t a finite number of ways for us to become Valid Successful People.

And that’s when you start to ask yourself: What is “success” anyway?

This question of “room” inadvertently defines success based on achievement rather than alignment.

When we ask ourselves “Is there room for me?”, what we are actually asking is “Is there room for me to be successful?” We don’t realize it, but it’s our ego hungering for validation and fearing failure.

One of the most profound shifts I’ve made in my life is changing my definition of success from being achievement-based to being alignment-based.

No longer do I define “success” exclusively in the sense that people buy my products or like the things I make. Those things rely on achieving some form of external validation, and I’ve found that no matter what milestone I hit when pursuing external validation, ultimately it only leads my ego to hunger for more or to aim even higher. In other words, it’s a recipe for dissatisfaction.

On the flip-side of that, however, alignment-based success says that my goal is to design a life and business where I can live out my core values on a daily basis. That is the source of all things good for me: happiness, satisfaction and freedom.

So when I ask “Is there room for me?” and I do so in the context of comparison or self-doubt, I’m slowly allowing myself to drift right back in that old achievement-based success framework, one where something isn’t worth doing unless I can gain financial success and visibility. That’s NOT what I want my life to be about chasing after.

When I shift this framework back to alignment, I can ask the question again, this time with a clarifying addition:

“Is there room for me to do the work my heart is calling me to do?”

When I frame it that way, I’m able to see that the primary goal in pursuing this idea or project in the first place is to express my core self. To follow a hunch or a passion or a curiosity or desire that is stemming from inside the deepest part of me.

And when I frame it that way, I can see much more clearly this definitive answer: YES.

Yes, there is ALWAYS room in this world for people doing the work their hearts call them to do.

“There is ALWAYS room in this world for people doing the work their hearts call them to do.”

There is room for me and there is room for you and there is room for us ALL to make the things we’re called to make. There’s a galaxy’s worth of infinite room where we can all try and learn and experiment and teach and lift each other up as we do so.

The moment we assume that there is one container limiting the expansive potential of each of us, we deprive the world of witnessing the beauty of our collective vibrance.

How Will You Define The Terms of Your Success?

If there’s one thing I want you to take away from this article and my wacky diagrams, it’s this:

You get to DEFINE what success means to you.

Keep in mind though, if you do select Diagram #2—the path of alignment—you WILL have to choose it over and over and over again. Your instinct WILL be to drift back into Diagram#1 and into the chase for external validation. You’ll want the milestone, the public pats on the back, that glorious feeling of being accepted into the tribe of humanity.

Trust me though, all of that will ring hollow compared to the glorious, sustaining satisfaction of being accepted BY YOUR INNER SELF every single day.

Last week I came across an interview of Maria Popova, founder of Brain Pickings, on and this excerpt that speaks to this notion perfectly:

“…I frequently get emails from young people starting out and asking, ‘How do I make a successful website or start my own thing?’ And, very often, it’s tied to some measure of success that’s audience-based or reach-based.’How do you build up to seven million readers a month or two million Facebook fans?’ But the work is not how to get that size of an audience or those numbers. That’s just the byproduct of what Lewis Hyde calls ‘creative labor,’ which is really our inner drive. The real work is how not to hang your self-worth, your sense of success and merits, the fullness of your heart, and the stability of your soul on those numbers—on that constant positive reinforcement and external validation. That’s the only real work, and the irony is that the more “successful” you get, by either your own standards or external standards, the harder it is to decouple all of those inner values from your work. I think we often confuse the doing for the being.”

A few weeks ago I was gifted a Five-Minute Journal and every day the journal has a line for you to write your own “I am” affirmation—a guiding belief that you can repeat every day to yourself. Here’s mine:

“I am ALREADY successful because I have designed a life that I wake up excited to live every day.”

I challenge you to redefine your own idea of success and write your own “I am successful because” statement, one that acknowledges the way(s) that you are already a success—to no one else but YOU.

Remember, this doesn’t mean that you have to stop striving, stop wanting to be better, or stop trying to create a brighter life. It just means that you take a moment of gratitude for how far you’ve already come.

When you already feel successful, you move forward from a place of abundance, not scarcity.

“When you already feel successful, you move forward from a place of abundance, not scarcity.”

When you are fueled from that place of creative satisfaction, you’re striving from a sense of peace, not poverty; fullness, not famine. From a place of WANT, not from a place of need.

I hope this article has given you the permission you need to redefine success on your own terms. Be careful not to confuse the doing with the being, dear friends.

It’s Okay If You’re Feeling Lost

June 24, 2018

Over the years I’ve dealt with feeling lost on many occasions. Whether it was taking my first step into the world of entrepreneurship (working for myself) or leaving behind a “successful” business (IWearYourShirt).

Feeling lost seems to be part of the human equation. Something we all have to deal with at different times in our lives, whether we like it or not.

I felt the most lost after an amazing weekend in Fargo, North Dakota in 2013 at Misfit Conf.

In May 2013, I attended a small conference in Fargo, North Dakota. I’d never been to Fargo before and the only thing I knew about the conference was that I was a speaker, and it was going to be a small, hand-crafted event put on by my friends AJ and Melissa Leon (of Misfit Inc).

Feeling lost at Misfit Con, Jason Zook and Srinivas Rao

Backing up for a moment, at the time (May 2013) I was running my IWearYourShirt business and things were in a huge state of flux. Actually, let’s just call it like it is: My business was failing completely and I was 100% burnt out.

My IWearYourShirt business had been my life-blood for the previous five years. It changed me as a person. It brought me amazing opportunities in life. It taught me so many lessons about running my own business. It also helped me build my first (awesome) community of friends, followers, and customers. But IWearYourShirt also took over my life, robbed me of all my time, and left me $100,000 in debt and 50 pounds overweight.

When my wife and I boarded the flight from Jacksonville, Florida to Fargo, North Dakota, I knew I was at a breaking point. Something had to give, I just didn’t know it would happen in front of a room full of strangers.


Why Was I Feeling Lost And How Did I Overcome It?

Let’s back up even further for a moment. In 2007 I left the 9-5 corporate world to start my first entrepreneurial venture. I took a huge risk to leave a super comfortable career as a web designer, to start my own design company with a friend. I had my first inkling of feeling lost at my comfortable 9-5 job. I felt out of place sitting in a beige cubicle. I felt incredible resistance to mundane meetings. I certainly didn’t see my work as meaningful, nor was I ever proud to share it with anyone other than my boss (for his approval, so he’d keep paying me).

I felt the least lost when I was in control of my day and my decisions.

As it turned out, working for a corporation or in my own first design company I realized I wasn’t really passionate about web design, websites, finding great clients, or any of that. I found that I liked working for myself and calling all my own shots. I felt the least lost when I was in control of my day and my decisions.

During the year and a half that I ran my own design company with a friend, the idea for IWearYourShirt came to me. I remember that idea giving me an incredible feeling of purpose. It wasn’t even a business yet, heck there wasn’t even a logo for it, but the idea itself gave me hope. It gave me a direction to go in. It gave me something that felt bigger than myself and something truly unique.

The first time I ever got over the feeling of being lost was when I chased a big idea and allowed it to have space in my life.

An emotional meltdown actually helped me deal with feeling lost

Having a mini emotional-meltdown on stage in front of a room of strangers helped me realize I was lost and forced me to start dealing with feelings I’d been internalizing.

Getting back to the beginning of this story, being a speaker at Misfit Conf presented me with a weird opportunity. I wasn’t new to public speaking and sharing my IWearYourShirt story with a room full of strangers, but this was the first time when I felt like I would be a fraud if I pretended everything was okay. If I just stood on stage and spewed the same stories I’d done the previous few years at countless speaking events around the country.

Instead, as I took the stage in front of 100+ people I didn’t know, I decided to admit I was feeling lost.

I remember sitting on a chair and saying out loud, “Normally I’d tell you all the good things I have going on in my life, but I can lie to you or myself any longer. My IWearYourShirt business is failing and I have to be honest about it.”

I don’t remember the next 45 minutes of my talk. That’s the honest truth. All I remember is snapping back into focus, seeing a room full of people with tears in their eyes, standing and clapping, and me feeling an incredible weight lifted off my shoulders.

For the first time in five years, I’d told a group of people that things weren’t going well. Every day prior to that I’d put on a face and a show.

I’d pretended and forced myself to say that life was perfect. I thought if I didn’t do that my community would abandon me and no one would pay me money ever again.

I stepped off the stage to a group of 100+ strangers who welcomed me with open arms. Where I’d been thinking people would ridicule me for admitting things weren’t going well, I was instead met with love and encouragement (truthfully I think Misfit Conf was the best possible place I could have had this emotional meltdown – that group was/is something really special).

When you’re feeling lost, something has to change

I had been dealing with feeling lost for months (maybe even years) leading up to that talk in Fargo, North Dakota. But instead of trying to acknowledge being lost, I suppressed my feelings and didn’t change anything. I tried to strong-arm my way through my problems, not realizing that I was merely putting tiny band-aids on a gaping open wound. When I took the stage, poured my heart and soul out, and was accepted for my failings, it was as if a switch was flipped.

My wife and I boarded our flight back to Florida and we spent the next few hours talking about everything we’d change.

  • Our spending habits
  • We’d get rid of the clutter in our home
  • I’d be more open with my feelings
  • We’d shut down my IWearYourShirt business for good

Let’s be honest with each other: Change is f*cking hard. It just is.

But without change, I realized I’d just keep digging myself further and further into a hole. I’d ignore problems and I’d hurt myself and the people around me that I cared about most.


How To Find Yourself Through Embracing Minimalism

At that same conference, another speaker took the stage and his name was Joshua Fields Millburn. With his beautifully coiffed hair, he spoke about his life and how lost he had been at certain times. His story really resonated with where I was in my life and I was eager to learn how he solved his own issues.

That’s when I learned about minimalism. Not about getting rid of everything you own and only having one chair in your entire home, but looking at everything you own (and choose to spend your time on) and deciding if those things are actually bringing you value.

Decluttering our home helped us combat feeling lost

It may sound silly to say that getting rid of a few household items made me feel empowered, but it’s absolutely true. The stuff we surround ourselves with takes more of a mental toll than we can see. When YOU are the one to remove something from your life that is no longer serving you, it feels great.

My wife and I started with our closet, getting rid of garbage bag after garbage of clothing we no longer wore. Clothing from our time in college. Clothing from when we were another size in our lives (damn you teenage slender years!). Clothing that we bought on a whim because we thought retail therapy would make us feel better about the things we had going wrong in our lives. It may be hard to believe, but my wife and I spent multiple hours in our closet laughing our way through getting rid of mountains of unused items.

Jason Zook and Caroline Zook embracing minimalism

From our closet, we moved on to other rooms in our home. It didn’t happen in one weekend. Our process of decluttering took weeks/months. But then I decided it was time to apply minimalism not only just to the stuff in our home, but also the business we ran out of our home: IWearYourShirt.

On May 6, 2013, I shut the doors to my IWearYourShirt business. As weird as it may sound, posting a status on Facebook about closing down my business felt better than most things had in my life at that time.

We re-painted our office, which was decorated for IWearYourShirt and all the videos I had been filming on a daily basis at that time.

IWearYourShirt Office, 2013

Rolling white paint over years of memories was equal parts sad and exciting. With each stroke, I felt like I moving toward a new life and new direction. Every brushstroke was one move closer to taking control back in my life.

From that day, we’ve continued to embrace minimalism in our lives. We sold everything in our home and kept only what we could fit in our small VW SUV and moved clear across the country to California. We’re proud to call ourselves minimalists, and we have way more than one chair!

Okay, truthfully, we only own three chairs and two stools, but that’s all we need.


Four Ways To Overcome Feeling Lost And How To Find Yourself

In 2014 my wife and I ventured back to Fargo, North Dakota for our second Misfit Conf. We spent the entire previous year rebuilding our lives and businesses. Getting rid of the things we no longer needed, and for me, sharing more of the thoughts and feelings I was keeping pent-up.

We hadn’t fixed everything in our lives, our businesses were still in flux, we learned three valuable lessons after our second weekend in Fargo:

Lesson #1 to avoid feeling lost: Give yourself permission to do the things you want to do

We all have ideas, goals, and dreams, but most often we are the ones limiting ourselves from making those things happen. It’s not money, timing, or any other factor, it’s giving ourselves the permission to just get started.

I wasn’t able to accomplish what I’d accomplished in the previous year because of luck or good timing. I intentionally changed things in my life and “sat in the chair” as Joshua Fields Millburn says. It wasn’t easy for me and it probably won’t be easy for you. The key is to make a commitment to yourself and to not do it alone. As proud of a person as I am, the best thing I did was give myself permission to start asking for help and being open to the change that comes with that help.

My wife Caroline deserves so much credit here. Not only because she was my biggest cheerleader in me giving myself permission to shut down my IWearYourShirt business and do other things, but also because she is so emotionally tuned-in and could help me navigate the thoughts and feelings I was having.

Lesson #2: Stop being so proud

I was too proud to ask for help. I was too proud to think I could figure everything out myself. I was too proud to ask people smarter than me for advice. I was just being too damn proud.

After the second year attending Misfit Conf, I decided to let my guard down a bit in hopes of figuring some things out about myself. I’ll be the first person to admit that I used to shudder at the idea of reading a self-help book or talking to a coach of any kind.

Acknowledging that I was being too proud made me feel like I was at least taking the first step toward working on these things.

I’m not sure where my too proudness stemmed from. I can’t remember a specific story from my childhood, but I’m sure there’s something there. Nevertheless, I remember being stubborn from a young age and I needed to change that. I needed to let go of trying to be in control of everything, especially my emotions.

While I do see pride as a useful tool in certain situations, it can also be a detriment if you have too much of it.

Maybe you’ve been too proud in certain circumstances that led to a fight with a loved one or a bad business decision?

It might be time to admit this to yourself and attempt to make a change.

Lesson #3 in how to find yourself: Stop trying to answer “what do you do”

This may sound dumb, but maybe you can relate. The question “what do you do?” had thrown me for quite a loop since 2009. Explaining IWearYourShirt to a random stranger in an airport who wanted to make idle chit-chat? That was always a hot mess.

I started to really resent the question especially after I shut down my IWearYourShirt business. I didn’t have an easy answer that quickly explained my weird entrepreneurial endeavors and each time I was asked thoughts of doubt and criticism swirled around in my head. I started to wonder why this question was bothering me so much and if there was a way I could fix it?

After multiple conversations with my wife, we both decided I should just accept that I was in a time of flux and experimentation. Sure, I didn’t have an easy answer at a cocktail party that could quickly define who I was and what type of work I was doing, but that started to not matter once I allowed myself to be doing a “floaty dance through life” (as my buddy Ben Rabicoff put it).

Once I came to terms with the fact that I didn’t need a clear definition of what I did for work to give me self-worth, I started to be more accepting of myself.

Lesson #4: Writing is cathartic

I never thought I’d be a writer. Heck, even as I type these words to you, it feels incongruent to the person I pictured I’d be in life. But alas, here I am. A writer. Someone who has typed millions of words, thrown the majority of them away, self-published a book, and written for many major publications. But it didn’t start that way.

Writing became my form of personal therapy.

My journey with writing consistently started with writing little blog posts about life and things that weren’t going so well.

I was incredibly nervous to hit publish and to share the first blog post I ever wrote that was the least bit vulnerable. But guess what happened? People celebrated my honesty. They didn’t critique all the bad grammar and poor sentence structure. They simply appreciated that I was willing to go out on a limb and to share something many people might not.

My writing went from a random blog post here or there from 2012-2013 to a consistent weekly post and email in 2014 to a small group of subscribers (just 400 people). Also in 2014, I self-published my first book, Creativity For Sale.

Writing a book was one of the most cathartic things I’d ever done in my life because I got to finally share so many stories of failure and mistakes that I’d kept bottled up inside.

In 2015 I started writing for Inc Magazine and a few other notable media outlets while continuing to write for my own audience (a group that became known as the Action Army). In 2016 and 2017 I stopped writing for anyone else and only wrote for my own audience on

In just a few short years I went from writing random updates on a Tumblr blog to having over 500,000 people read my writing in 2017. Can you believe that? It’s hard for me to believe!

Maybe writing could be an outlet for you? You don’t have to start by publishing your writing. Maybe it’s just a journal you keep? Or a daily writing practice you do for one hour per day that lives in a Google Doc that only you know about? Give writing a shot, it was instrumental in helping me overcome feeling lost.


Feeling Lost Is Something We All Deal With, Don’t Try To Get Through It Alone

While I do believe some solitary activities can help, like writing, if you’re currently feeling lost you should absolutely reach out to someone. Is there a peer in whatever industry you’re in that has been down a similar path to you? Or maybe finding a therapist in your local area that is highly well reviewed? Therapy has such a negative connotation, but people like my wife swear by it (and we celebrate its effectiveness in our house!).

We all deal with feeling lost at certain points in our life. And I hate to be the bearer of bad news, but even if you overcome a big milestone of feeling lost like I did in 2013, you’ll be met with more bumps along the road.

If you want some book recommendations, I’d highly recommend The Obstacle is the Way and Body of Work. Both of those books were really helpful for me and continue to provide lessons for my life.

I’d also highly recommend giving minimalism (your own flavor of it!) a try. Decluttering your life can lift more weight off your shoulders than you’d ever imagine.

You aren’t on this journey called life alone. There are people around you who want to support and help you. Be willing to open up to them and be willing to ask for help. It was difficult for me, but it was also the best thing I’ve ever done.

The “18not180” Approach to Becoming Your Best Self

January 8, 2018

I talk a lot about becoming your best, brightest self.

Sometimes, though, I fear the way I talk about personal growth makes it seem as though once we discover what actions we want to take to live as our best selves, that seemingly overnight we’re able to simply make those changes and accomplish just that.


We decide we need to be more self-disciplined so we wake up the next day able to stay focused and on-task, and suddenly we’re living our best life.

We decide we need to rest and take better care of ourselves, so from then on we no longer overwork ourselves and burn out and, ta-da, we’ve changed!

But that’s NEVER how it actually works, is it?

It took me so long to learn this. For so long I tried this strategy: I’d find myself in a moment of “I know I’d be so much happier and brighter if I just did better with xyz.” I knew what needed to change, and maybe I even made better choices for a while, but a month or two later when I went back to my old ways, I felt like a failure.  I would judge myself for sliding backward, not making that change.

That awful feeling of letting yourself down… I’ve realized that’s often the most powerful force that holds us back from real growth. We judge ourselves for “failing” and the next time we don’t even try to do better because we’re tired of feeling the guilt and disappointment of not being able to suddenly wake up and do a 180.

But last year I tried something new. I realized I needed to stop making the goal to do a complete 180-degree change in whatever area of my life I was focusing on.

Instead I started asking myself: What if I just focused on trying to get 10% better at whatever I wanted to change? 

What if I just focused on trying to get 10% better at whatever I wanted to change?

What if I drank more water 10% of the time? What if I was better about reaching out to friends just 10% more? What if I managed my daily schedule better just 10% of the time?

By changing the goalpost to something so seemingly manageable, I stopped finding myself in the dreaded loop of self-judgement.

Lasting change and living your brightest life ultimately comes down to tiny micro choices. In any given moment, you can choose what feels easy and comfortable OR you can choose what that best version of yourself would choose.

Imagine you are a dial or compass pointed in one direction. Most of us view change as a complete 180 degree rotation to get ourselves pointed in a new direction. Instead, this new philosophy has me viewing change as the sum of tiny 10 degree turns toward whatever that “best” version of you looks like.

Jason calls this 10% better strategy “18 not 180” (which, coincidentally, feels especially appropriate for the year 2018).

So my challenge for you this week is to think of the one or two most pressing areas of your life or habits that you are trying to change, and I want you to try getting just 10% better.

Try rotating those measly 18 degrees, not a full 180. See if it feels easier and more doable to slowly drift toward your brightest life, rather than feeling guilty or disappointed for not being able get there overnight.

#18not180. I’m making it a thing. A gentle reminder. A mantra. A cheat code. Whatever you want to call it, I hope it helps you make 2018 your best year yet.

Thanks for reading!

Embrace Change By Letting Go Of The Past

October 23, 2017

Anything that drops in and shakes up almost every facet of your day-to-day routines is what I like to call Big Change.

It could be moving across the country or starting a new job or ending a serious relationship or deciding to start a family.

In general, Big Change can be quite terrifying, mostly because the uncertainty that it brings about is overwhelming. It’s not like you’re swapping out one tiny piece of the puzzle; it feels like you’re busting up the whole dang thing, mixing up the pieces, and starting over again.

That alone is enough to get someone’s anxiety going. But what makes Big Change even scarier is when it’s brought about by something that is not your choice.

Maybe it’s a relocation because of your job that you didn’t see coming, or a landlord deciding to sell your rental property ?, or being broken up with out of the blue, or even a family crisis that completely turns your world upside down. Whatever the circumstances, this kind of Big Change curveball can send you down an especially stressful spiral because on top of the overwhelm there is a lack of control.

I don’t know about you, but uncertainty mixed with lack of control is the recipe for my ultimate cocktail of stress (aka Anxiety On The Rocks… I do not recommend it.)

When we humans start feeling a lack of control, our natural instinct is to reassert it in any way we can. That’s why, when confronted with Big Change, you’ll likely find yourself tightening your grip on whatever reality you feel you’re about to lose. 

Your mind will become preoccupied with all the parts of your day or life that will no longer be the same. Things you never paid any attention to will suddenly feel like precious treasures. (During a break-up:) We’ll never brush our teeth together in the morning again… (Or a move:) That barking dog next door is so cute, I’ll really miss him… (Or a shake-up at work:) I know I always complained about that project, but I’m going to miss complaining with Rhonda after our status meetings…

These are not the things we’re actually grieving the loss of, though. We’re actually just grieving the loss of familiarity, of comfort, of certainty. 

In our case, this move wasn’t our idea. It was brought about by something completely outside of our control. Our initial reaction to that was exactly what I described above — clinging as tightly as possible to the home and life we’ve assembled over the past year and a half.

My mind became obsessed with all that we’d no longer have around us: the ocean view from our bedroom ?(#firstworldproblems), our perfect walking loop to take Plax on twice a day, our amazing neighbors that are just a few feet away.

The more I focused on these things, the sadder I became for our impending move because it was beginning to feel like a big loss.

What I started to realize though was that while those things aren’t necessarily trivial, they’re not the real source of my sense of loss. It’s not about the ocean— it’s more about losing the certainty that we’ll have a way to connect to nature every day. It’s not about our walking loop—it’s about losing the sense of comfort in a daily routine with Plax. It’s not about moving farther away from our friends—it’s about not knowing for sure that we’ll make the time to hang out and maintain our sense of community.

Once you recognize that the discomfort isn’t necessarily coming from losing the elements of your life themselves but just the overall loss of certainty, then you can work on solving that.

First, find ways to make the uncertainty of the future more concrete. List out all the positive things you know this change will bring.

With Big Change, there’s always something you’re losing but there’s also always something you’re gaining. 

The secret to embracing Big Change and minimizing the discomfort of uncertainty is to shift your attention to what you’re gaining.

For us, that’s embracing the awesome new neighborhood and location our new place is in. I’m looking forward to having an entirely new environment to set up my art studio in and my workspace — those kind of changes often leave me feeling renewed and refreshed.

We can also start replacing those “losses” I listed above with new interpretations. Our daily dose of nature becomes the park just up the road. I can start envisioning our new walking route with Plax, and look forward to the patch of grass we have in our new backyard so he can roll around. I can make a goal to host a dinner with our former neighbors at least once a month.

Bringing these new puzzle pieces together might help you feel energized by the changes before you rather than terrified by them.

Once you start to bring your focus to the future and find things to get excited about, the final step is to release that death grip you have on the past.

It makes us feel more comfortable and in control to think about what’s right in front of us, but clinging tightly to a reality that’s expiring only makes moving forward more painful. It leaves us with one foot in one reality and one foot in a new reality. I’ve seen enough science fiction shows to know that’s a recipe for being torn right in half.

So your challenge this week (whether you’re in the midst of Big Change or any kind of change) is to: 

Let go of what WAS in order to embrace what IS.

“Let go of what WAS in order to embrace what IS.”

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If you’re the type of person that has trouble embracing change or relinquishing control, I know these strategies aren’t the easiest thing in the world.

But I also know that life never stands still for long. The more we can learn to embrace the never-ending process of evolution, the more we can continue to live as our brightest selves, whatever curveballs may come our way. 

If you’re not in the midst of change right now, I hope this week’s letter encourages you to take a moment of gratitude for the chapter you’re in. What are those things that you’d miss if you were moving away? Try finding a way to enjoy them today as you would if you were moving soon.