2021 was an incredible year. Perhaps one of the best of my life. It was a year of writing my book, fully leaning into the opportunities that my path has opened up, preparing and moving to the US with Angie, starting to find more joy in day-to-day life, and the best year financially since being self-employed.
This is the first time I’ve sat down to write an in-depth review of my year. In the past, I’ve only done a quick scan of questions and a surface-level review of my business.
However, inspired by other people who have shared their reviews, I thought I’d do my own.
In this review I’ll cover a few things:
- Three things to celebrate
- Three lifestyle experiments & lessons
- My five favorite places
- Overall Financial Results from 2021
- Business experiments & learnings from 2021
- Pivoting from freelance to “creator” – five year reflection
- Questions and themes I’m thinking about 2022
Before we dive in, some stats:
- Countries Lived In: US, Taiwan, & Mexico
- # Of Accomodations >1 Week: 14 places Puerto Escondido, Mexico City, Taichung, Taipei, Hualien x3, Taitung, Green Island, Orchid Island, Kenting, Taichung, Connecticut, New York City
- Total Accommodation Expenses For 2021: ~$8,500
- Total Estimated Rent for 2022: Much Higher
- # Of Hours Spent on The Book: ~1,500
- # of Vaccines Gotten In Taiwan: 1
- # of vaccines in the US: 1 (15 weeks after the one in Taiwan)
- Published words in a book: 57,500
- # of Green Cards Acquired for the Wang/Millerd Family: 1
Three Things Worth Celebrating
Inspired by Chris Spark’s own beautiful reflection where he details “five celebrations” I decided it would make sense to do the same. With the recent release of my book, I realized that I don’t spend much time celebrating myself. This is partly a good thing – I’ve created a path that isn’t tied to outcomes, status, identities, or things like promotions.
However, as I’ve become comfortable detaching what I’m doing from any sort of extrinsic reward, I think I’ve become a bit too shy about being excited when good things do happen or even stopping to celebrate just because it’s something worth doing.
So here are three things that I’m really happy about with 2021:
- Angie getting the green card!
- Moving to the US and being able to do it with an optimistic and excited attitude
- Finishing and shipping my book and in the process pushing myself beyond what I thought I was capable
#1 Angie getting the green card!
Although we haven’t got the physical card yet, we went through a 13-month process of endless paperwork and Angie was given a green card to be a permanent resident of the US. It’s so great to see this journey through her eyes. She said something a couple of months ago: “I don’t think you know how lucky I am to have this opportunity.” Despite many people being negative about this country, many people abroad still want the chance to live and work here.
I’m excited to see the US through her eyes as we continue to spend more time with my family, make new friends, and travel the country.
#2 Moving to the US and being able to do it with an optimistic and excited attitude
When I left the US in 2018, I was searching for a new way forward in life. I was also a bit lost – I had become disconnected from myself and didn’t know who I wanted to be.
A few years later I can say with a lot of confidence that I’ve found myself – as cliche as it sounds. I’m married to an incredible woman, spend almost every day doing things I am 10/10 excited about and have a great foundation of friends and family across the world to support me.
Yet I was really scared about moving back to the US for most of the year. Angie and I applied for her green card in late 2020 and our plan was to spend most of 2021 in Taiwan waiting for the completion of the process. Due to the incredibly slow speed of the immigration process, this meant I had a year to prepare.
I decided to “practice” optimism.
The first step was remembering. Remembering who I was when I was younger and figuring out how to inject the joy, enthusiasm, and humor that were once such vital and natural parts of how I showed up in the world back into my life. This was hard. I did a number of things like talking to some of my optimistic friends more, writing about my fears and doing things I loved as a kid like Tennis, Basketball, Yo-Yoing. Through all these things, I realized how rigid I had become as an adult and it made it even more clear how important it is to continue to look for ways to inject a playful attitude into my life.
In our first couple of months back in the US we lived with my cousin Brian in New York. This was a great decision because he’s someone that I’d describe as fully alive and engaged with the world. Loves his job, has plenty of things he’s excited about and is constantly getting pumped about what other people are doing. In only a couple of months, I realized that I really had changed a lot in a few years abroad and was able to channel completely different energy than in the past.
Another thing was concerns about money. I realized early on in the year that worries about the skyrocketing cost of living in the US were beside the point. I knew how to make money if I needed it and we have some savings to let us still invest in our life without needing to earn a lot in the next six months. So I decided to commit to not complaining about money whatsoever and instead start with the life, locations, and things we want to do and then worry about making the money for it later.
Put more simply, I found out who I am and now I have a lot of confidence I can show up in the world as I want to, less impacted by the criticism and pessimism of others than I have been in the past.
Feels awesome!
#3 Finishing and shipping my book and in the process pushing myself beyond what I thought I was capable
In my book, I write about the “real work of your life” as finding the things worth doing and then committing to them. The book was the biggest project I’ve committed to on the pathless path and it has been by far and away the most rewarding.
In addition to pushing me well beyond what I thought I was capable of in terms of writing, it also was a learning experience. I had worked on complex projects, but nothing like a book. At almost every stage of the process, I overestimated how quickly things would take and underestimated how much work I would have to do.
I had complete confidence the entire year that I’d be able to write the book I wanted to but I didn’t know how I’d get to the finish line. This is where my experience in consulting, to trust the process amid ambiguity, really helped. I would write for an extended period, take a step back (time off), then restructure and write again. I went through this process four or five times and each time I felt like I was getting a little closer.
It wasn’t until a couple of weeks before leaving Taiwan that I figured out what the book was about. It came to me after being frustrated with writing and Angie suggested I go for a scooter ride around the town. Less than 30 seconds into the ride, everything came to me and I started crying.
A voice in my head was telling me: “these ideas matter and you don’t need to be scared to say that.”
I knew that in order to write a book I needed to unleash the bold side of me that I had kept back in my writing and in my life.
These ideas fucking matter.
I also was able to connect it to seeing my parents struggle and knowing how much more capable they were than what the world was telling them they were allowed to do because they didn’t have degrees.
It was a book for them and the hundreds of people I’ve talked to over the past few years but also the world. And from there, the rest of the book seemed to pour out of me like it had been there the entire time. By mid-December I knew I had the book I was proud of and from there it was just editing and getting the details right.
If you haven’t bought it yet, check it out here.
Lifestyle Experiments & Learnings
I’m living a life far beyond what I thought possible five years ago. Most days I wake up and work on whatever I want to do and have the freedom to go wander, exercise, meet up with friends, or go for a bike ride most days if the opportunity presents itself. At the same time, I’ve found work I love doing – writing, curiosity conversations, mentoring, creating digital products & teaching online.
Despite this optimal existence, I am still fascinated with how motivation shifts based on where I’m living, who I’m surrounded by, and what I’m curious about. This means I’ve continued to experiment and learn about how I like working.
Three key themes stand out from 2021:
#1 Improving my Chinese skills during an intensive class that also aligned with a three-month period of living my “ideal life”
In March, I took an on-campus class in Taipei studying Chinese. I found it incredibly enjoyable. In addition to the 30+ hours of in-class instruction and studying, I was also spending time biking around in the afternoons, writing my book, and still running my StrategyU business.
It made me remember how much I loved learning and that if I can build in similar blocks of intensive learning throughout my life, I will likely be a very happy and engaged person.
Each day, I had class from 9:00-12:00 and then would ride my bike around campus and the city. From there, I might grab lunch with a friend, wander a bit, or do some writing. During this time, I also hosted my first corporate workshop, which helped me develop a corporate offering for my course, which already has its first client in 2022.
I was “working” a lot and there was no clear separation between night, morning, weekday, or weekend, but it was a period of absolute perfection. Everything I was working on was by my own creation and on my own terms. I couldn’t have been happier.
This was also when I started to realize that this is why people struggle to talk about work. They tend to only be talking about “jobs” rather than the work they want to be doing. Most people want to work, we just accept that some or a lot of it are supposed to be a grind. Most of my path has been about running away from that and along the way, I essentially realized what I was doing was “designing for liking work” (h/t Venkatesh Rao for pointing this out to me.)
#2 Inspired by Sean McCabe, I tested, implemented and have committed to a “every 7th week off, no matter what” model for at least 2022.
Inspired by a conversation on our podcast and looking for better ways to structure my work, I implemented Sean’s “take every seventh week off” sabbatical approach.
In our conversation, we both had opposing reasons for doing the experiment. Sean originally did it because of overwork and I wanted to try it because I felt like I had a lovely life, but wasn’t quite going all-in on the projects I was excited about.
Now in each six-week block, I plan on picking one or two priorities work-wise and trying to focus on those. During the past year, it was vital in helping me power through different phases of the book before taking a week off to wander and reflect.
#3 People over work
Coming back to the US I was excited to see some of my friends again! In New York, I decided that I would prioritize meeting up with anyone who asked over any work I might be doing.
This was great at first but I was a bit too ambitious in terms of how much socializing I wanted to be doing after a year of relative solitude in Taiwan.
In Austin, I’m finding a good balance again and am also excited to have a home base for at least five months where I can get back into a solid routine.
Five Favorite Places of the Year
Mirador de Tortugas: An amazing sunset spot Angie and I found in our last month in Puerto Escondido. After finding it, we proceeded to design our day around making it there for sunset each night
Dulan in Taitung, Taiwan: If there is any place that has more of a hippie nomad energy in Taiwan, this is it. Situated right on the cliffs on the southeastern shore of Taiwan, this is a much quieter place in Taiwan that attracts a lot of young and international people.
Fuli District In Hualien, Taiwan: Between an epic bike ride through the greenest rice fields I’ve ever seen and the beautiful golden needle flowers, this place was magical
Green Island and Orchid Island, Taiwan: We spent a week on each of these islands in September and both were unique experiences. Orchid island feels like a completely different country than Taiwan while on Green Island, I found another place filled with beautiful views.
Austin, Texas: I’ve only been here for three weeks but I am blown away by how much we’ve enjoyed the energy of the city, how relaxed and friendly everyone seems to be, and how nice the weather is (half of each week at least)
Business Results, Experiments & Learnings
Overall this was my best year since becoming self-employed. I say this from a completely holistic perspective. It was both my best year financially and my best year personally. In addition, the amount of work I did that was based on me needing to join specific meetings or be available at certain times of the day was less than 20 hours for the entire year.
A win for async work!
Overall Financial Results
Overall here’s where I ended up according to my accounting software
- Revenue: $102, 567
- Net Profit: $72,257
- Self-Employed Taxes: $16,195
- Net Income after Self-Employed Taxes: $56,062
Of course, these are only estimates – actual US taxes paid and potential rebates are yet to be determined.
Here are breakdowns of earnings and costs by source (costs are assigned on a % basis according to revenue). All earnings are after transaction fees.
Results By Business Focus
StrategyU: $87,510
Developed a clear advertising strategy. Created, piloted, and won first client for $15k corporate virtual workshop program. Ran for BFCM deal using Brennan Dunn’s playbook => $13k in Black Friday sales
- Think Like a Strategy Consultant: $74,531
- Corporate Workshops / Training: $10,897
- Digital Products: $2,082
Costs: ~$24,209 (majority contract labor + advertising spend)
Profit Margin (pre-tax): 72%
Boundless: $8,905
Focused on writing consistently (newsletter & book) – 72 subs for Boundless. Launched Freelance Skills Course (~3k in Sales) – an opportunity for marketing in 2022. Does not include $5k investment in Book
- Newsletter: $3,906
- Courses + Digital Products: $3,787
- Book Pre-Sales: $1,212
Profit Margin (pre-tax): 90-93% (estimated)
“Passive” Income: $8,905:
YouTube revenue saw some decline throughout the year, but peaks in Aug-Sep
- YouTube: $2,148
- Other: $2,713 (includes bounties from AppSumo, affiliate deals from Teachable, Podia, Convertkit, courses and payments from Skillshare, Amazon, and Medium)
Profit Margin (pre-tax): 90-93% (estimated)
Coaching: $4,025
This is from 1-on-1 coaching earlier in the year and group coaching kicking off in December.
Profit Margin (pre-tax): 90-93% (estimated)
Five Biggest Experiments & Lessons
#1 – Think Like a Strategy Consultant had its best year – Traffic continued to increase on my website and Youtube with very little effort to add additional content. I hired two ads people in Croatia who have helped me implement an effective advertising program. It hasn’t gone as well as I would have hoped, but I definitely see more potent
#2 – Prototyping, launching & selling a Corporate Virtual Workshop – Last spring, a data analytics company in the US wanted to train their team with my self-paced online course. I decided I would develop a corporate workshop for them and sold it to them at a discount to help me prototype it. It went far better than I expected and I ended up developing a clear “signature offer” for my course to pitch to companies.
#3 Productizing other stuff on StrategyU – Inspired by this post on Austin Church’s site, I decided I needed to take some of my own advice and develop “packages” for some of the work I liked doing. One reason was to make it simpler for the increasing number of corporate types who were stumbling upon my page and also to create easy on-ramps to working with me.
Here’s an example on the coaching front. I make it cheap and easy (but still have a cost) to talk with me but also signal that I do higher-end work (with high price signaling). Using this I’m already working with two senior executives in 2022 to help them with Board presentations (which I love doing!)
Here’s an example of the corporate workshop. It clearly signals that I am only working with serious companies that are willing to pay my fee. If they aren’t they can self-select out and I save the time I might spend on a phone call.
#4 Shipped my freelance course – In June after being locked down in Taiwan after a local outbreak, I decided to create a freelance course that had been existing in my head as a future potential creation for more than a year.
I think it’s a pretty badass course on helping people become strategic partners to senior-level business leaders. It walks through the nitty-gritty of everything from proposals, to documents, to pricing, to what to say in conversations. I am still not sure if I should integrate this with StrategyU or keep it separate but I’m guessing the answer will emerge this year as I plan to put a bit more effort behind this in 2022.
#5 Group Coaching – Throughout 2022, I had more people asking questions about finding other people following similar paths. Inspired by Tim Ferriss’ question, “what if this were easy?” I decided to create a survey gauging interest in group coaching. I got 30 responses and from this, I created a landing page, some stripe payment links, and sent out an announcement about doing cohorts starting in December. I’m currently running an “early career” one and a “mid-career” one and both are going really well! I think group settings are much better for the work stuff than 1-on-1 because I only have so much experience. I’m not sure what I’ll do next with these but I’ll likely scale up to something more interesting
Reflecting on the past five years
On the business front, I seem to be nearing successful completion of a pivot I originally made about 9 months into self-employment when I realized I didn’t want to spend the rest of my life as a freelancer. At that time, I was also realizing I wanted to optimize for non-work time over almost everything else. This led to a dramatic decrease in earnings (2017 was only 7 months!) and a shift to a different way of thinking about work. You can see the transformation here in these two charts:
In this first one, we see that for 2018 and 2019 I wasn’t making much money (which was fine at the time, I wasn’t too focused on making money)
What I was focused on instead was developing skills, experimenting with creating online (which I found I really loved), and finding new income streams beyond freelancing. For most of 2021, I had >10 income streams with 3-5 earning me more than $200 a month:
The biggest driver behind this shift was the slow but steady growth of my course Think Like a Strategy Consultant. The course has generated more than $172,000 in revenue over the last three years, far exceeding anything I could have ever imagined.
Through the course, I’ve had a ton of inbound requests to work with me and because I only wanted to work on things I liked doing, I’ve purposely only accepted things I want to test and then potentially turn into an offering.
Over the past two years, I’ve now developed a pretty robust corporate offering, a coaching offering and am even turning this experience into freelance strategy work with corporate strategy groups and boutique consulting firms. I’m pretty excited about most of this because it’s work I like doing, am good at, and it doesn’t take too much time.
You can see this shift in the following chart:
Luckily, this has given me a lot of time and space to continue to write and explore my curiosity around work. While the course has provided most of the income, most of my time has been devoted to writing for more than three years.
For 2022, here are five questions and themes themes I’m thinking about for both work and life:
#1 How do I use my happiness, optimism & energy to support others?
I’ve found my footing as a self-employed creator/solopreneur/whatever you want to call me. I’ve also reclaimed some of my childhood excitement towards life. The question I’m asking this year: how do I broaden the sphere and support others with this energy?
#2 How do I level up the ambition in ways that are exciting and sustainable?
My fear five years ago: creating a job for myself. I now am quite confident that’s not going to happen. I know what drives me, how to fire up my curiosity, and I know when to say no. With this, I’m thinking about ways to be a little more ambitious with what I’m doing. I’ve been comfortable tweaking and making 1% improvements over time. I don’t have any interest in 10x-ing anything but am interested in potentially doubling the scale of the things I’m doing and looking for other ways to help people beyond my comfort zone.
#3 How do I help Angie succeed?
My wife is amazing – smart, curious, and creative. How do I continue to make sure she is able to do the things that bring her alive while also having the resources to take chances and risks in order to grow. I think about this a lot but it’s worth writing down here as a gentle reminder.
#4 What are the business or personal things I’m not thinking about (yet)?
Angie and I are always asking some form of this question. It’s an easy way to keep dreaming and imagining new possibilities. It’s very easy to know what the default next steps are, especially in the US. Everyone in my age cohort seems obsessed with owning a home. It all seems a bit too frenzied for me right now not to mention it’s just not my goal. However, that means we often need something to aim for. Right now seems incredibly open after finishing my book. I don’t need to have an answer but I’m listening for clues.
#5 What are the experiments I can do to continue to grow?
This year is all about play, experimenting, having fun, joy, and trying to remain optimistic. To do this I plan to continue to do things like play sports, Yo-Yo, hosting events, and then try new things. Some things on my list: tap dancing, DJ lessons, and hosting a party using Nick Gray’s new book. In addition, I want to write more essays, create more YouTube videos, do some deeper writing for StrategyU, potentially do a meditation retreat, and much more.
