10 Things, 2020 (incl. Health, Travel, Money & Special Announcement) | Boundless #122

10-part recap on pandemic, writing, financial + special announcement

January 1st, 2021: Greetings from Puerto Escondido and welcome to 100+ subscribers in the last few weeks including Steven, Peter and Ted who became paid supporters (special 🎁 for subscribers at the bottom). What follows is a 10-part recap on 2020, some reflections on the places we’ve been, update on financials and my work and goals for 2021 (or lack thereof)


1. Our pandemic started in January

I started the year in Taiwan. For us, the pandemic started during the week before Chinese New Year in January. News of the pandemic in China was everywhere and given how the SARS pandemic had spread through East Asia in the early 2000s people were both scared and prepared. I left my apartment sometime around January 20th and walked onto the streets of Taipei. I noticed that 100% of people had masks on. Shame sent me back up to my room to grab a mask (most people had masks on hand already and expect this will be a new norm everywhere).

I tried to make sense of what was emerging online. It seemed as if Taiwan had acted in time and was keeping the virus under control though almost everyone was thinking it might only be time until East Asia was going to be a hotspot. It was my assumption that given more time to prepare, places in Europe and the US would be able to fare even better.

I was wrong.

2. Leaving Taiwan

We had already decided to spend the next couple of years traveling around the world and our mental model was that this pandemic would follow the course of the original SARS pandemic. So we thought it made sense to get out of Asia ASAP. We decided to skip our first stop in Vietnam and head directly to the canary islands in Spain.

As soon as we arrived wearing masks we realized that almost no one else had had been living in our reality plus most of the Chinese-Spaniards had scooped up the masks to send back to their families. It was weird seeing crowded events and bars and wondering what might happen. Our anxiety caused us to skip several of the carnaval events in Tenerife that were later linked to the initial outbreak in the Canary Islands.

The canaries ended up being a great place to be locked down as it was 72 and sunny every day and we got to share a beautiful coliving house with 5 other nomads. By the time the canaries came out of lockdown there were almost no cases on the island so we had an opportunity to explore for a month or so.

3. Health Challenges

I’m writing this in week 3 of fighting some god awful parasite or infection here in Mexico. If I had any job at all this year it was powering through long stretches of health uncertainty. I spent about four months in Spain and the US dealing with nerve damage and extreme fatigue from a tooth extraction. It was hell, but I benefited from having my wife by my side and my past experience fighting a two-year chronic illness that helped me know that deep down, things usually get better.

Somehow I think of the moments in Spain fondly despite the health issues. I seem to be lucky to have a brain that tends to turn almost any circumstance into a worthwhile one upon reflection.

However, I write this under duress and am a bit exhausted from going day to day not knowing how I’ll feel. Hopefully next years reflection doesn’t have much on my health.

4. Spending Time At Home

We flew out of Spain in July on a plane with 12 other people and exited JFK in under 10 minutes. We spent two weeks quarantining and then got to spend eight weeks with my family in Connecticut, including quality time with my Nana.

It was a fascinating experience spending so much time with only my family with multiple cousins working remotely and getting a taste of what I’ve experienced over the past few years. It seemed with this experience that people were starting to realize what I have been aiming for - more flexibility to spend extended stretches of time with family.

It’s been a tough year for her as she has been a lone a lot in her assisted living facility. She’s 91 and gets the vaccine next week. I can’t wait for that.

5. Road Trip

At the end of the summer my health was starting to turn the corner and me and Angie had the idea (along with every other millennial) to drive across the US. We had not spent much time out of our hometown in the US so it was a nice opportunity to explore the country together and even think about where we might live if we end up returning to the US.

The best (or maybe worst) thing about a road trip is that you will cement about 10 songs deep into the recesses of your brain . Here’s a sampling of our very pop-oriented playlist.

6. Online Energy & Existential Crises

Starting in April I had a flood of people reach out with mini-existential crises they were facing with their relationship to work. The pandemic seemed to be a wakeup call for many making them realize it was time to move, time to make a leap, time to have kids or time to re-assess their relationship with work.

Although I’ve been writing about these topics since 2017 it was encouraging to see the world move in my direction a little. More importantly, it was cool to make new friends who had many of the same questions I’ve been writing about.

Twitter was a great place to connect with these people and a lightweight way for me to share some of my questions when I was battling brain fog. I had a few tweet threads that seemed to connect with people that you can peruse here.

I also had curiosity conversations with 100+ people from around the world. My conversations with strangers every Wednesday continue to be an absolute delight and I’m glad that many have turned into ongoing penpals and sometimes in-person friends. I hope to meet many of you over the years to come and if you haven’t set up a call yet, grab some time here.

7. Helping others

One of the coolest “projects” I worked on this year was helping a local chef here in Puerto Escondido with pictures, a promo video, a website and some business cards so that he could start putting himself out there. He had the hard part down - creating damn good food - but didn’t know where to start in terms of getting his name out there. If you’re curious or ever headed to Puerto Escondido, check out his site here.

This is the most fun part of having a flexible schedule. If you are looking for any help launching creative endeavors in 2021 let me know how I can help!

8. Funding & Reinventing The Journey

I went into this year without any clear goals for my businesses but my StrategyU YouTube channel exploded randomly at the beginning of year and I was able to start monetizing. My following grew from 1,000 followers to almost 9,000 as of this e-mail. This led to earning “YouTube" money” which was not something I aimed towards nor realized was a thing at all until it happened.

I’m trying not to get too distracted by YouTube. I did level up my video skills this year but its not the thing I really enjoy doing. However, it did signal to me that there is a larger demand for the stuff I’m creating with StrategyU than I realized and I invested in building a lot of the infrastructure for my course.

My course, Think Like A Strategy Consultant really took off in April and May, likely fueled by excess cash, an increase in online learning and working from home. I shifted away from a cohort-based model and towards a two-tiered self-paced or hands-on coaching model. This also led to the realization that I was both very good at and enjoyed 1-on-1 presentation coaching with executives. After successful small projects with a CEO, a startup pitch deck, a tech executive, and a small team on data analysis it will likely become the sole focus of my consulting work moving forward.

This continues a shift away from consulting work (essentially the kind where I do long-term projects with one company) and more towards working with individuals through my course and an interestingly growing pie of content revenue over the last 4 years:

And by month:

Enabling this was a 14 month period (months 17-31 approximately) in which I purposefully oriented my life away from work and money as the center and avoiding saying yes to freelance projects. This was kind of a crazy thing to do at the time since I was just getting the swing of freelancing but a deeper pull towards this path kept grabbing my sttention. I had saved up some money before I quit my job and after 9 months I had more or less broken even. At this point I decided I would try to break even or even spend some savings for the next year or so and in 2018 and 2019 I earned about $20-$30k each year. I wrote about this shift and an embrace of non-doing on my blog earlier this week.

As you can see I just had my best month in December. 2020 will likely be 2.5x the income I earned in 2019 which is pretty mind blowing considering how out of it I was for half of the year.

I honestly have no idea what to expect for 2021 but its all part of the journey and I’m glad to say that in year four, I’m definitely doing the work I want to keep doing. Which to me is the only point of going off the default path…

9. Lots of fun writing this year

This is the year in which I feel like I hit a stride with the newsletter and am still having a ton of fun sitting down every week to write. It’s kind of crazy that the newsletter almost tripled going from 1,200 people to 3,076 people and with 50 people choosing to support me as paid contributors.

If you are new here it might be worth exploring some of the older issues or some highlights from this year:

On my site I published a few pieces which were either extensions of newsletter musings or deep longform explorations. Here are the ones I enjoyed writing the most:

It’s kind of crazy looking back on this and how many good things I wrote over the last year. Last year I realized upon reflection that writing had become one of the things I enjoyed most and I tried to design my life such that I had space to think and write.

10. Aims for 2021

We are headed back to Taiwan in a few weeks and will likely be there until vaccinations reach a critical threshold. My one explicit goal for the year is to improve my Chinese and I’ve already enrolled in a semester long class at NTU from March-May.

In terms of work goals, when I reflected on 2021, StrategyU kept emerging as something to focus on but I couldn’t find a reason other than “make more money.” Given that I have enough right now, that really isn’t a good reason and generally I’ve found that when I go against the default options, interesting things happen.

The thing that does keeps emerging is writing, so my intention for 2021 is simple:

Try to write, most days.

That’s it. And to raise the stakes, I’m announcing a a scary goal, a book. If you’re interested in grabbing a pre-order you can do so here or if you are a paying Patreon or Substack patron, grab your free code here.

📚 Grab a Pre-Order of The Book


That’s all for now. Onward to a fulfilling and healthier 2021!

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