#1 It’s still far more rewarding than I ever could have expected
For years I had a low-grade dissatisfaction with my work. At the simplest level, I just didn’t like having to go to work every day and I hated having to do tasks that seemed pointless.
It now seems obvious I should have embarked on a path like this much earlier. It suits me. I am a bit sad that I never got to be on this path with my 20s energy. I think it would have been pretty fun.
Generally, self-employment continues to give me a sense of ownership over my life that feels great.
#2 I’ve changed a lot and not so much at the same time
On one level I’m very different than I was ten years ago. I rarely go out, I don’t drink, I don’t spend much time watching sports outside of basketball, my career ambitions are no longer legible, I prefer to spend more time in solitude and reflection, and I am married with a child.
Looking back though, a lot of the changes I went through were not as much about changing who I was but rather shedding a social self and identity I had consciously manufactured in my twenties.
Now, I feel a bit less like some crazy person who threw away a certain kind of life and more like myself.
Many of the things I am drawn to are very much the same: I read a lot, I learn new things, I seek out thoughtful people and conversations, and love helping others succeed.
But if you’re someone who sees people as the sum of their accomplishments and material possessions, then yes, I am certainly quite different than I was at 29.
#3 Alcohol was probably a bigger negative on my life in my twenties than I used to think
In writing my second book, I’ve been reflecting a lot on my twenties. How did I keep doing work I so clearly didn’t care about for the second half of that chapter?
Part of the answer is inertia, another part is lack of imagination, and another part is alcohol. It’s hard to ignore how much alcohol was part of my previous career life. I drank and partied most weekends. I always had plans. But soon after I quit my job, my drinking and going out slowed, and then it dropped out of my life, as I’ve written about before:
I stopped drinking for the second time when I moved to Taiwan. I never planned to quit. It just happened. I went to night markets instead of bars, met my now wife who doesn’t really drink, and slowly the desire disappeared.
I never really had a good explanation for this but through writing and reflection, I think it’s related to my capacity for navigating fear, uncertainty, and discomfort. During my career life, I was constantly busy, either working, socializing, or plotting my next job hop.
I remember panicking if I didn’t have plans for the weekend. I’d text everyone I knew. I’d always find something. I was a “Thank God it’s Friday” guy. A few beers or more with friends and things felt lighter. I never saw it as a big deal because I was a joyous, happy drunk, usually surrounded by friends.
Now I just think back and wonder: how many of us were trying to escape our lives through the buzz of an IPA?
This is obvious now because I’m on a path and in a life I don’t want to escape. It feels nice. It’s impossible to see this from the outside but the experience is vastly different than in my former life.
#4 I’ve gotten less experimental with my work in the last few years
With more success in everything I’m doing, I’ve been more in maintenance and promote mode than tinker and experiment mode. This was amplified last year as I was mostly in family mode. I’m hoping to change this in the next couple of years. I’m probably going to pause the podcast indefinitely, write this newsletter a little less consistently, and look to play a little more in new scenes and spaces.
For me, there is a consistent lag between my initial curiosity about something new and how it shows up in my life as something that I end up doing and also can generate money.
My income declining a bit this year is due to the lack of experiments in the past few years and I know I’ll need to come up with things that might pay the bills 2-3 years from now.
It’s time to tinker.
#5 I still find it hard to fully embrace boldness or risk
I have a base level of optimism that is something like: I feel like I can keep going on this path and will figure out how to make it work, even if I don’t know how.
But that optimism is mostly about my confidence in being able to avoid failure. “Continue making it work,” is not about crushing it or being a seven-figure entrepreneur but about breaking even and not shrinking my net worth.
I have a harder time embracing something like: I am optimistic that if I take bold risks and aim higher, I will not only stay in the game but thrive.
I am friends with people who think like this and I am always amazed. They hire people and spend tons of money, aiming at a bigger future. Their faith in their ability to succeed.
The game I’ve internalized for a long time is one where I optimize my energy, interest, and enthusiasm to keep going. My bet is that most people quit these kinds of paths and since I like what I’m doing, there will likely be unexpected rewards if I can simply stay in the game over a long time and keep improving.
Some of this has come to fruition. 50k copies of The Pathless Path is nuts. I still can’t believe it. It was more or less me executing the strategy of continuing to stay connected to my work above all else.
But is this the right strategy moving forward? If I’m being honest, I’ve benefitted from being early to building things online and the fast growth of the internet economy. With more people playing these games, and doing it with much bigger war chests and boldness, can I continue to hack a living playing a long, slow, stupid, fun game?
With less time after becoming a dad, I’m finding myself a lot more willing to make some bets. I’m currently testing out an operator to come on and run StrategyU and also investing in a high-quality print edition of The Pathless Path. Both will require 5 figure investments but I’m not as scared of making these bets.
Will it suit me or will I be defaulting back into the survive and thrive strategy that’s so far served me so well?
Time will tell.
#6 Writing has become more important over time
I love writing. It continues to be a challenge and playing with words is immensely satisfying. I was feeling a bit bummed about writing my newsletter recently but here I am writing this post and enjoying it once again.
Although writing has been the central activity of my life for seven years, it has only generated more than half of my income in one year so far. This was due to a huge run in sales last year. This year, writing will again be a minority of my income.
But it’s still surprising how much writing has shaped everything I’m working on. I originally started writing about consulting and problem-solving in the early 2010s on Quora, and those ideas have helped me build a pretty interesting side business. And then I started writing about work in 2015 and almost ten years later, I’m about to
In the last five months, as I’ve been heads-down in book-writing mode, I’ve been having so much fun with my work. I also trimmed away most other things I was working on and have been building my weeks only around writing, reading, and family. It’s really nice. I know I definitely want to write one more book and I’m already thinking about how I can structure a workyear to facilitate that on an ongoing basis.
#7 The Next Decade: Parenting & My 40s
The next decade of my life will be intense. It’s probably the end of the “prime” of my creative career and also the “magic years” for my kids.
The big question for me is, “How do I thread the needle of working on the things that matter to me while still being intentional and present with my family?”
For many people in traditional jobs, you can sort of bank on cozy upper-level positions that pay well in big companies and don’t demand too much of you as you age.
For me, I suspect it will look a bit different. By 50, I expect my enthusiasm for hanging out online, starting new projects, and forging new connections will be diminished. So I am feeling a lot of pressure (and excitement) to try to be a bit more pragmatic in making bets in the coming 10 years, seeing it as the final chapter of this creative career.
Will I likely keep doing work that matters to me much longer? Sure. But I just don’t think it’s reasonable to bet on a high level of enthusiasm and energy maintaining itself for a very long time into my 50s and 60s. So I’ve been playing with a question:
How do I fully retire from work I’d rather skip by 50?
Right now, I don’t have a good answer. Angie and I both enjoy our creative work and we’ve found that we’ll likely need some childcare support in the coming years. This means a bit more spending, especially in the US. It seems impossibly hard for me to figure out how to make all this work but I’m also somewhat excited but this question. I love being pushed to be creative with thinking about how to live life and generating new solutions. We’re exploring many things such as moving abroad, exploring things like cohousing, moving near friends, and even moving somewhere cheaper in the US, and I’m enjoying having to think through all of this. And also contemplating if there is a bolder sort of thing I could lead or be a part of. I am not quite sure yet but I will likely be sharing my thinking process here over the coming years.
I’m on this path because I cherish having this responsibility over my life. You may think stable jobs are easier, but for me, that feels like the worst thing on Earth.
Which is a good thing because it means I’m still having fun.
7 years down, 70 more to go.
