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Our 2023 Year-End Review and 2024 Preview

Wandering Aimfully Through Intentional Living

Our 2023 Year-End Review and 2024 Preview

Jason ZookJason Zook Jason ZookJason Zook

Written by

Jason Zook

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:

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:

*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 2023 Year-End Review and 2024 Preview

(Big Fat Takeaway)


This article written by

Jason Zook

I'm all about that Cinnamon Roll life (that just seemed like a "cool" way to say I love baking and eating cinnamon rolls). Also, I co-run this WAIM thing as well as Teachery. Currently, 75ish% completion of Tears of the Kingdom 🧝‍♀️⚔️.

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