May 27th, 2023: May 26th is my annual self-employment anniversary. I can’t believe it’s been six years already! I also hit 25k sales on my book this week which just continues to be mind-blowing. We are heading back to Taiwan for a couple of months this summer and I was reflecting on the decision to move there about five years ago. Hope you enjoy…
#1 GO AND FIND OUT
Six years ago this week, I took the 7 train from midtown Manhattan one stop to my apartment in Long Island City. It was the final commute home from the office. I haven’t done anything like that in 2,190 days since.
When I was making that final trip home I had little to no vision of what might come next. I was running away. I had spent my final year of that last full-time job dealing with the frustrating bureaucracy and failure of grown men to make decisions and my own inability to put up with it. It nearly broke me.
It’s funny how naive I was about what might come next. I had done the tactical things one might do like registering an LLC and creating a website for my consulting brand but I had somehow overlooked the fact that my entire mental model for how the world worked might get burned to the ground and need to be rebuilt.
My writing has been the main tool I’ve used to rebuild. It’s a slow process but each week I learn a bit more. I look back and try to increase the resolution of what happened in the past and then look forward, trying to experiment with new recipes that might enable me to stay energized, creative, and inspired.
The reason I orient around these things is because of a decision I made a year after that final commute. I had just returned from a month-long trip to Asia and I felt a deep force telling me to return. It wasn’t rational. It was a deep feeling in my gut and nothing else. It’s easy to look back and say fate was pulling me to Taiwan but I sense there are 100 alternate scripts of places I might have ended up.
The most important feeling I had was that I needed to go somewhere. It really didn’t matter but the most important thing was that I needed to leave the US.
On September 3rd, 2018 I headed to Taiwan with two carry-on suitcases, and in the first five weeks, I had already met my soon-to-be wife Angie, and found a deeper connection with writing.
That first month was magical and it changed my life.
It was a month of wandering without a plan. For the first time in adulthood starting with the beginning of college, I existed for a month solely as myself. No plans and no identities. Not as a consultant, MBA student, or worker on a successful path. It was just me, hacking a living on a single mattress in a tiny room in Taipei spending less than $30 a day. No one knew anything about me and most lacked the ability to ask.
In that month, I experienced the evaporation of the default scripts in my head. Over the previous year, I had tried to be fully present but could never escape the frenzied-doer mind that is hard to ever quiet while living in the US. You can’t just wander around in the middle of a day on a workday. You should be working.
By living abroad I was experiencing the perspectival shift that people have been writing about for hundreds of years. I had thought that I had changed a lot in that first year after quitting my job when we stay in our own country it is nearly impossible to see how deeply everything is embedded in our being. As Clifton Fadiman pointed out once, “a foreign country is not designed to make you comfortable. It is designed to make its own people comfortable.” But for me, by putting myself in an uncomfortable position, I experienced the paradox of finding more comfort in myself and my life than ever before.
Existing in a state of non-doing and feeling called to write was a powerful transformation. It changed everything. And when I met Angie soon after, she was one of my biggest supporters despite my lacking any sort of story or “plan” for my life.
And this is why I’m so bullish on doing things like living in another country. Not a vacation. Not a “trip".” Just going somewhere to live. It doesn’t matter if you do it later in life or fit in into your 30s like I did. It’s a way of tapping into a deeper and more relaxed state of being that many of us never have time to experience.
You might wander around as I did for a few weeks and notice that the thoughts from back home start to dissolve. For the first time, you will experience a state which feels calm and peaceful. You will walk into a grocery store and be amazed at all the new fruits you’ve never seen. You will start to become curious about the world. You might even spontaneously start crying in a park that has trees from all over the world because you are filled with love and joy. And after a few weeks of this, you might wonder if you are ready to go back to your old grind. You might consider retiring some of the stories and scripts in your head that you grew up with instead.
It’s hard to know though what will really happen…but don’t you want to find out?
#2 Talking Work With Simone Stolzoff
I dropped a podcast this week with my friend Simone Stolzoff. He just published a book The Good Enough Job. Last year, he shared an early draft of the book and I was impressed. Almost all mainstream writing on work centers around an “anti” script, why the current system is broken. But Simone skillfully avoided this and a lot of it was from his own journey with his own relationship with work. This is a tricky thing to pull off but he did it.
The book is a collection of ten different modern stories of people grappling with the modern reality of work. The best parts I think are his own personal journey and the references to historical ideas around work.
We didn’t talk a ton about the book directly but we did go much deeper into his personal story on my podcast. It was a fun conversation
LISTEN: APPLE | SPOTIFY | YOUTUBE
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I visited Taiwan for the first time this past February. My fiancee is Taiwanese, and we went to spend time with her parents and otherwise experience the beautiful island. Even the two weeks we spent there were profound. When Jackie and I got back to Austin, we were inspired to plan for more extended "wandering time" in Asia.
We don't know what it looks like yet, but your writing is certainly nudging us to roam! Thank you!
Happy self-employment anniversary! Always a cool milestone to stop and let soak in. Just passed my 3-year in Feb :)
Also, epic to see the convo with Simone, gonna give that a listen on my afternoon walk today!