2024 was a year of liminality. Our last full year in Austin, not knowing where we’d go afterward or when we’d leave. A year of deepening into fatherhood, finding my creative groove again, and then losing it. A year of supporting Angie’s creative awakening and laying the foundation for what’s next. It was a year of endless laughs, joy, friendship, and love—and a year of frustration, loss, and change.
My “long 2024” was about 16 months from December 2023 when we rented our place in Austin for a year to April 2024 as I sit here about to drive to Houston to fly to Taiwan..
Knowing 2024 might be our last year in Austin, we splurged on a fancy apartment by the water. Given my instinct to bank any cash for future freedom, it felt uncomfortable, but it was a good way to celebrate the unexpected windfall from 2023 book sales and create a nice environment to spend more time at home with Michelle. No regrets.
On the work front, both Angie and I rediscovered our creative grooves after struggling in 2023 to balance it with having a kid.
I started and finished my second book, Good Work, while Angie made real progress on her memoir, finally breaking through years of resistance, and is on the homestretch. She is on track to publish her book in Chinese later this year.
Finally, in March, Angie got U.S. Citizenship, which is incredibly exciting. While it was a moving experience for both of us, it also feels like the 50th procedural hurdle in a plan set into motion in 2018 when we decided to get married. From our marriage to applying for a green card to moving to the U.S., and carefully managing every step to stay within the bounds of what was legally allowed, the last five years have been a meticulous dance with bureaucracy..
We are really excited to be a bit more free in the coming years.
Some highlights from 2024
- Countries Lived In: US
- Countries Visited: Mexico
- Places Visited: Valle de Bravo, Mexico City, Boulder, Healdsburg, Connecticut.
- # of Podcast Episodes Published: 14 new episodes
- # of Newsletter Issues: 32 main issues, 4 guest posts
- # of Books sold: ~14,000 (about 3k of Good Work)
- Revenue in 2024: ~$256k
- Profit in 2024: ~ $129k (53% margin)
Things worth celebrating in 2024
- “Still pathless” for 7+ years, making it work financially and also as a parent (see: seven years self-employed)
- Switched to a new agent for my foreign rights which led to multiple opportunities, including translation deals in India, France, Russia, and China, as well as re-publishing locally in Malaysia and India. Also finally landed one of my only goals for the book in the last couple of years: getting republished in Taiwan.
- I hosted my first real “book launch” event in Austin, with friends. A couple of years ago, I wrote about my struggles celebrating myself. This event
- Co-hosted an event in SF around the launch of my new book with Cissy Hu with 50+ attendees
- Wrote and published my second book
- Successfully brought on a business partner for my StrategyU corporate training work, with her taking over with leading and running the work in 2025
- Started investing in developing a premium hardcover version of The Pathless Path with Otterpine, with it scheduled to be released mid-2025
Writing in 2024
The best thing I wrote this year was my book, Good Work. Outside of this, I’m not all that impressed with the rest of my work, though there were a few notable essays:
- How I sold 50k books: essay and video recapping the crazy journey I’ve been on with The Pathless Path (the video also got shared in Tim Ferriss’ newsletter)
- Seven reflections on seven years of self-employment: A fun riff on working for myself for seven! Years
- A week in the life as a creator & parent: I had meant to do one of these for years. This one will be fun to look back on.
- How I write: 18 reflections on my approach to writing. A good companion to my interview with David Perell on his podcast of the same name
- Escape Shouldlandia: A reflection on escaping a world of “shoulds”
- Laptop Man & New Work Realities: a riff on an emerging new kind of work person
- Popup cities and coliving experiments roundup: worth checking out if you are interested in the growing scene of digital nomad/coliving experiments around the globe
Answering Open Questions From The End of 2023
Where do we want to have a home base for the next 3-4 years?
This question feels less pressing than it did last year. Whenever Angie and I are trying to permanently “solve” this question, we get stressed. I think early on as a parent, I had a sense that picking a permanent home was something I was supposed to be doing.
But as we’ve gotten the hang of parenting and realized that Austin wasn’t going to be the place, Angie and I are open to having less of a home base and are planning on being semi-nomadic, anchored in Taiwan in the coming few years.
This is the first time in five years that we have not had to legally live somewhere due to visa or immigration reasons, and we are enjoying this freedom.
How am I blocking myself right now?
In 2023, I was creatively constipated. I didn’t produce enough, and it made me grumpy. Coming into 2024, I was determined to change this. This meant questioning all previous approaches to work, including my “write whenever it feels good” approach that was the foundation of my work life from 2018 to 2022. Writing Good Work I forced myself to find a new working rhythm, which meant working outside the house for the first time in years and committing to a weekly writing cadence, writing Monday, Wednesday, and Friday mornings no matter what.
This was hard. I had to pause, slow down, or stop several things I’ve been doing for years, like my podcast, newsletter, social posting, and general tinkering/experimentation. In my book, I called these activities “supporting activities” – they are the ones that fuel my energy, give me ideas, and are fun – but are not my “good work.” The balance of these, as I proposed in my book, is a constant “puzzle” that I must solve over and over again. I’m excited to continue tweaking and trying to find a balance over time, but my gut is telling me that I should be spending a little more time in “play mode” with my work, including reviving the podcast.
How can I spend more me-time this year?
At the beginning of the year, Angie encouraged me to take a solo trip to Boulder to visit my friend Jonny. The trip was rejuvenating and was the first break I took for myself after the first eleven months of being a parent. Taking solo trips was something Angie had always done but I never felt called to do. I had always found enough time for myself throughout with my minimal work schedule. But now with Michelle, I just wasn’t finding the time to slow down, using any time I had for fitness and work.
I had about 7-8 days by myself during a work trip in LA, the Boulder trip, a book launch party in SF, and visiting Edge Esmerelda in California. While most of these had some sort of “work” component, I was still able to slow down and take time for myself during each. They were helpful anchors to a year that seemed to fly by.
My natural tendency is to put others first and to sacrifice my own well-being but these trips have made me realize in order to show up at my best, I need time for myself too. I’ll likely be looking to be even more deliberate about this in the future, perhaps even doing my first meditation retreat or something along those lines.
Can a three-day workweek work?
I wrote a bit about my intention to do this in February. While the beginning of the year was focused on executing two major projects for StrategyU clients, I shifted toward writing in March and for six months was able to commit to a weekly writing routine. Every Monday, Wednesday, and Friday, I focused on writing for three hours. It was delightful and was how I found my way “back” to a good relationship with writing again.
As I finished the book in September, I pretty much stopped this schedule, working even less and taking more of a lead role with parenting as Angie finished her 2nd draft of her book. This latter part of the year was pretty intense. I was doing wakeups most mornings and also watching Michelle solo 3+ days per week.
I have no regrets, but I did have to come to terms with the fact that I did miss a lot of the work things I’ve done in the past, especially the random rabbit holes and side quests that made up a lot of my “work” time. While it makes sense in my head to prioritize and “claim” time for writing, I’ve had a hard time scheduling and following through on spending time on random things like reading, tinkering, and experimentation – things that don’t seem productive but tend to be the seeds of future opportunities on thai kind of path.
Angie and I are plotting a different approach to things in 2025 and beyond that likely will be a bit more sustainable, but given how much I’ve enjoyed spending time with Michelle in her first two years, I really want Is do I work more or do I lean even more into parenting?
How do I get people to come to me?
The goal with the bigger apartment was to have more friends over for dinner parties and coworking days. While coworking was impossible once my daughter started walking, we did host many dinner parties. This was a great way to continue learning how to cook while also getting to spend quality time with friends on our schedule. Despite being busy, we never regretted having people over, and it’s a reminder to keep doing this. People rarely care how clean your place is or what you serve. People just want to spend quality time with each other.
On the work front, I intentionally tried to co-work with other writers outside of the house, and this was a great success. It was great to spend time with other serious writers. This helped both confirm how much I enjoy writing and to take my future ambitions with writing more seriously.
Work Reflections:
Spent more money on work stuff than ever before
In 2023, I talked about investing more money in my work. I set a goal of investing $20k into my work and various businesses and came up short. This year, I made a bunch of investments and passed that mark.
- Hired a community manager to help with the pathless path community
- Hired a part-time operator for StragegyU on a trial basis and then brought her on as a partner for my corporate training business under a revenue share agreement. I’ve already paid out multiple payments.
- Starting the process of creating a high-end collector’s version of The Pathless Path with OtterPine, a project that will likely cost about $25,000 and another $20,000 for print costs (if anyone wants to potentially sponsor some of this, let me know!)
Found an Operator for my StrategyU Training Business
As mentioned above, I found someone who was leaving McKinsey and looking for an alternative to formal employment. After a three-month test run, she decided to join as a partner on a revenue share basis for my Stra
This is pretty exciting as it’s the first attempt to build beyond myself.
Turned down an acquisition offer for StrategyU
Through my efforts to find a potential operator for StrategyU, I ended up finding another person that had experience in digital education and was interested in acquiring the business.
At the end of 2024, he offered to acquire most of the business. It was exciting to have someone interested in acquiring something I’ve spent years building, but it required me to stay involved in the business for another four years. While I still would have retained some upside in the business. in an agreement where I’d earn back equity and still have a share in the profits of the business. I realized that without owning the business, I’d likely lose motivation quickly (even if there was a massive upside).
Shifted The Pathless Path Community to a one-time fee
The admin work required to sync monthly payments between Substack and Circle was far too much. I shifted back to a one-time payment, which I’ve used in most parts of my work, and immediately knew it was the right move.
Instead of having a steady number of people in the community, this has led to growth in the community, leading it to have a little more energy beyond me providing it.
This year, I’m exploring doing some group projects with the community as part of a collective.
Open Questions
Should I work more or work less?
An interesting reflection I’ve had on the last couple of years is that it’s been frustrating to work less, especially on the things I care about, but if I had to do it again, I 100% would.
Even though parenting is draining, the time I spend with Michelle feels immensely satisfying when I look back.
But at the same time, the creative side of me gets extremely antsy when I’m not creating.
Sell StrategyU or not?
When I think about the next year, the big question for me is: should I move on from Strategy U or not?
The business has been great and has helped fund this journey. Now, I’ve found an operator to run the consulting business. But the question that I keep coming back to is: Am I just delaying the inevitable? What’s on the other side of letting that go?
It feels like part of me from a past life that I’m still clinging to, and the amount of energy I need to whip up to work on stuff from the business continues to inch higher. I don’t really know what the right answer is, but sometimes, staying with the status quo is a good answer, too, or at least delaying the decision. I sense something will emerge as I’ve put some things in motion that are unfolding right now.
Future Writing Projects?
I spent some time in early 2025 tinkering with LLM writing tools, and it’s having me rethink everything from the ground up about how I approach my journey and path as a writer. I think, on one hand, I’m going to be able to be far more prolific and productive in writing. On the other hand, I can sense that perhaps things that I might have wanted to write in the past may not be as satisfying if an LLM can just whip these things up. I want to at least publish something in 2025 that is not my hardcover reprint. One project I’ve kicked off is working on a magazine with the Pathless Path community, and that should be fun. Let’s see where that goes.
Future income streams?
As I approach the eight-year mark, I realize that I’m on my third iteration of how I make money. The first phase was making money from consulting, and then I started making money from Strategy U and my online course. From there, it was through workshops that were attached to that course, and then in 2023, it was from my book. As book sales start to diminish, I am thinking through what the next opportunity looks like for making money. I notice I spend a lot of time maintaining past ventures, and that may not be the best use of time for generating the income that will help fund the next 10 years of our lives. I will probably do some experiments this year to see if there are any ways of making money that feel good and are in the flow of what people might be looking for.
Host events?
One of the things I keep thinking about that still feels exciting is wanting to host writing retreats or events for Pathless Path people somewhere in the world. With my move back to Asia, I think it will be a lot easier on the cost side to host something. I plan to do at least one event in 2025, and we’ll see if that leads to something else.
Some More Photos From The Year
