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Our 2020 Year-End Review and 2021 Preview

Wandering Aimfully Through Intentional Living

Our 2020 Year-End Review and 2021 Preview

A look back on 2020, what went well, what didn’t go well, and what are we focusing on for 2021.
Jason ZookJason Zook Jason ZookJason Zook

Written by

Jason Zook

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.

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:

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:

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! 👋👋👋

Our 2020 Year-End Review and 2021 Preview

(Big Fat Takeaway)

We enjoy writing these year-end reviews so we can look back on where we've been and look forward to where we hope to go in the future!


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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