Permission to Travel | #305
August 12th, 2025: Greetings from Chiang Mai! I’ve been leaning into the “most weeks” promise of this newsletter this summer, but felt called to write this morning. Enjoy.
Shoutout to Vinamrata Singal and a few others in my community who are creating After Moonrise, a short film about grief and healing between mothers and daughters. Her goal is to tell stories that help families move toward each other as we grow up and start seeing our parents as whole, imperfect people. While they’ve hit their funding goal already, you can still support here or learn more about the project here. We live in an age when this kind of thing is more possible than ever, and I love being able to shout out people doing stuff like this on their own.
#1 At Home
“Travel won’t fix you.”
“Everywhere you go, there you are.”
People love to repeat these clichés as a way to dunk on people who seek transformation through travel.
Alas, I don’t resonate with them. Moving abroad and living in different countries has been a very positive experience for me. Immersing myself in other cultures, like Taiwan, has helped me loosen the grip of the American cultural scripts in my head. Living in places like Spain, Thailand, and Mexico has helped me meet people living differently and valuing things like family above work. Living in so many different places doesn’t make me feel unsettled; I feel grounded in a deep sense of possibility and wonder for the world.
Everywhere I go, I feel a bit different, and that’s kind of nice.
I sometimes wish this weren’t true. It would be easier to be in one place and live life like everyone else. But the longer I’ve been on an indie path, I’ve gotten more and more sensitive to where I live. This seems to be something many others on indie paths experience, too. I’ve heard from so many people that they can’t handle the chaos and noise of a busy city anymore. Many people have left places like NYC to go to a tier-two city and then smaller and smaller places until they find the place that feels right.
In different parts of the U.S., I feel different pressures. In New England, I feel pressure to fit in. In Texas, I am drawn to freedom. In California, it seems like I should have a lot more money, be involved in twelve different startups, and be friends with more weird rich people who could fund my work. When I’m in Asia, I find solitude from the buzz of American media and politics and feel like it makes sense to put my family above everything, including money and work.
When I’m by the mountains, I’m drawn to contemplation. By the beach, I feel gratitude. Near the roar of cars on the highway, I feel frustrated. Wandering through a night market, I feel like a kid again. Close to a plaza, I want to sit and yap. In a suburb where no people are around, I am desperate for others. By a lake, I feel at peace, and in a park where my daughter wants to go down the slide one hundred times, I feel complete.
When I’m in a city of millions of people, I feel immobilized, not wanting to go through the trouble of a long trip to meet people. When I’m in a smaller village, I want to meet and connect with everyone. When I have to drive, I tend to stay home. When I can easily bike somewhere, I find myself looking for any excuse to be outside.
No place is perfect, but we have found many great-for-now places. Taipei was one, and then Austin, and now Chiang Mai too. In 2021, before we moved back to the U.S., Angie and I tried to answer the question of where to live once and for all. After toiling for about a week, Angie suggested that we don’t need to find a perfect answer; we could just keep asking the question.
A lot of anxiety can disappear if you stop trying to solve things once and for all and just accept that some questions are meant to be asked.
When I think about where to live, I remember: There is no perfect place. There is no arrival. There is only here, right now, and life itself.
For most of my twenties, however, I wanted an answer for my life. I hopped from job to job trying to find the perfect solution for work. When I quit, it was the first time I stopped trying to find an answer in the world of the employed.
When I moved abroad fifteen months later, it was the first time I realized how much of the pressure I felt to have answers for life might have been because of the places I had lived.
Wandering around Taipei was the first time I thought to myself: I don’t have to know where I’m going.
And somehow, that’s the first time I started to feel at home.
#2 Podcasts!
I published a few podcasts over the last month:
The Inner Game of Work With Pranab Sachi
A conversation with a friend, Pranab, who is experimenting with a new kind of coaching to help people work through blocks they have while working. I think he’s onto something pretty interesting, sort of an applied IFS for work.
Building A Global Schooling System for a World With Remote Work
I chatted with Rekha Magon, the co-founder of Boundless Life, about her journey with work and also her experience running an international school in almost 10 locations around the world. I have multiple friends who have participated in these cohorts and have great things to say!
Money Beliefs & How They Shape Our Reality
I enjoy Nick Maggiulli’s writing. He always brings nuanced data to a hot-take world. He recently put out a 2nd book, and I used the opportunity to have him on my podcast and chat about all things money and unconventional paths that I’m thinking about as I’m working on a book on the topic. We had some friendly debates around freedom (I think people can easily obtain it with less money, he seems a little more fixated on getting rich first).
Thanks for indulging my explorations
I’ve been doing some form of public writing since 2015. I’ve somehow figured out how to hack a living doing things like exploring random seapunk rabbit holes for eight years now. I’m amazed myself, don’t worry.
If you like what you read here, you’ll probably enjoy my books The Pathless Path and Good Work:
If you’d like to meet others on “pathless paths”, you can join The Pathless Path Community.
Some things I endorse: Readwise for book notes and reviewing highlights; Readwise Reader for my attempts at re-creating RSS readers (2 months free for each. Crowdhealth, an alternative to US health insurance that I’m still using while abroad; Kindred, a home-sharing app; Collective for handling your S-Corp accounting needs; and Nat Eliason’s Build Your Own AI Apps course
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I love this. Something that really helped me shift my perspective: while I was living in London I decided to study a masters degree at a kind of hippie college in Wales. I was so used to the career driven culture of London. But while studying I met fellow students, young and old, living interesting and unconventional lives. Lots of them did seasonal outdoor work. Many were activists, grew food, were involved in community projects. Few had a conventionally 'comfortable' life but they seemed happy in their own ways. It totally opened the window of possibility for me to ditch corporate work and forge my own path.
"A lot of anxiety can disappear if you stop trying to solve things once and for all and just accept that some questions are meant to be asked." Love this perspective, great essay, Paul!