Since December 2024, we have been living nomadically, traveling with three suitcases, a stroller, and a pack-and-play. We’ve lived in the US, Mexico, Thailand, Hong Kong, Korea, Vietnam, and Taiwan, with multiple trips back and forth to Taiwan throughout that period. We stayed in 22 places for a week or more, with the longest stay in any single apartment being five weeks, and the shortest being two days. We lived in several different cities: Austin, New Braunfels, San Antonio, Dripping Springs, Oaxaca, Taichung, Taipei, Hualien, Hong Kong, Chishang, Da Nang, Hoi An, Koh Samui, Chiang Mai, Busan, and now back in Taipei. We just signed a one-year lease in Taipei and are expecting a second daughter in July.
We have no plans to go anywhere for a while :-)
Depending on who you are, this might sound awesome, or it might sound slightly insane. I welcome all judgments here on the Pathless newsletter, but thought I should at least attempt to jot down some reflections — both for my own sensemaking, and your bemusement.
#1 We had planned to move back to Asia for a while
We definitely enjoyed living in the US over the last three years, especially in Austin, but just felt increasingly pulled back to Taiwan as our daughter started speaking Chinese.
We faced some challenges with the second pregnancy, and because of that, we decided to travel around a bit longer before settling back in Taiwan. So for the last year-plus, we spent one month in Mexico, three months in the US, five months in Thailand, coming back to Taiwan for three months for my Taiwan book launch events and for Angie to finish her book, and then heading out again with 20 other families as part of the traveling village in Vietnam, Taiwan, and then Korea from January to May.
As that was ending, we signed a lease for a mountainside apartment in Taipei, where we’ll be settling for a bit, awaiting the arrival of our second daughter in July.
Someone asked if we are “settled down for good,” and I didn’t quite know how to answer. We are settled for now, and may be here for a few years, but at least for us, the concept of being settled isn’t a worry or goal. It’s actually nice knowing we could be in many locations and figure out a setup that works for us.
#2 Long-term travel is definitely a skill, and you need to rebuild some of those skills when you travel with kids
Having lived in so many places with Angie, we’ve developed a lot of interesting “hacks” to help us be quite satisfied living almost anywhere. This includes minimum travel periods (1 month), budgeting for upgrades in the first few days, and the general capacity to handle things going wrong that comes with, well, things going wrong.
With our daughter, we’ve had to develop even more skills like finding play options for her, finding formula, diapers, and childcare on the go, strategic boarding and flying strategies, and adjusting to different food availability. For the most part, although travel days can be a bit more stressful, traveling with our daughter has not been that hard. In fact, she’s injected quite a bit of joy into going to new places because she gets so excited about new apartments, new places, and trains. We’ve stuck to a pretty regular rhythm of sleep that seems to be the most important thing when having young kids. When she sleeps well, we sleep well, and when we have a rough day, we remind ourselves that we’d be facing the same challenges no matter where we lived.
I’d say the hardest time to fly was the period between 13 months and 17 months because she had just started to walk, but could not understand that you can’t crawl down the aisle during takeoff, and had zero attention span to be distracted by an iPad or literally anything. Outside of that, it was a bit stressful but generally not too bad. Out of fiftyish flights over the past few years, I think we might have had 1-2 rough ones.
#3 The challenges of traveling with a young kid are just the challenges of parenting anywhere
Wherever you go, there you are, as they say.
The biggest challenge with traveling with our daughter was that we continued to take on most of the childcare ourselves, and this just got a bit harder as she got older. One of our best setups was finding a part-time nanny while in Oaxaca for the month. In Koh Samui, we tested out something that was a little more social, as she hadn’t spent much time interacting with others. It was awesome on paper, and she loved the teachers, but she kept asking us to get rid of the other kids from the school.
This led to a change of location and also inspired my father-in-law to offer to join us in Chiang Mai to help watch our daughter through most of the second half of last year. This period was pretty magical, and he seemed to be enjoying spending time with her after retiring from his office job, though I think he was starting to hit his limits toward the end, too. Angie and I got a bit more time to connect, we found a small group of friends in Chiang Mai that we hope to spend time with again, and we both had more time to work on various projects, especially giving Angie the space to finish the final draft of her book.
At the beginning of the year, we headed to Vietnam to start the traveling village…
#4 The traveling village was awesome, but also challenging, and a lot of that was just the unique demands of our specific daughter being about three
I am so glad we did the traveling village, and with a little time to think over the past few weeks, I’ve been able to put the experience into perspective a bit more.
The positives:
Being around families while traveling who face the weird challenges of living a nomadic life with kids was inspiring and gave us lots to think about
For me, being around many dads who valued spending lots of time with their kids felt great. In Austin, spending 2-3 days a week with my daughter felt a bit lonely and weird. On this trip, with almost all the other dads being incredibly involved (if not the lead parent), I felt much more at home. Many of the fellow dads are in a downshift or break from work to focus on family over the next few years. It was very inspiring and reminded me that not everyone is career-maxxing.
For Angie, being around many moms balancing motherhood, creative work, and personal time was energizing and rewarding in the same ways
Our daughter connected really well with a couple of the twelve-year-olds on the trip who babysat a number of times throughout the trip, and it was the best “it takes a village” experience.
As I reflect on the trip, I realize that the busyness of the trip made it hard to really digest all the really cool experiences we had as a family. I suspect this experience will have many memory dividends in the future.
Kamal, one of the dads on the trip, threw these amazing birthday parties, including one for me, where we played basketball, I got to DJ, and also hung out with all the dads. I’ll always remember my 41st birthday, one of my favorite ones in a long time. These dads’ nights out were a highlight: There’s something special about hanging out with fellow dads putting their family first. Although we were from many different countries with all sorts of different energies, we shared a strong common bond, and I loved the feeling of shared respect in the group.
Also, some challenges:
Our daughter has always been a bit on the shy side (see “get rid of the other kids” above), and so the large group meetups (a “nest” four days per week) were a bit tough. I would be excited to be around the other parents, but I couldn’t quite hang out with them because my daughter would either want to go home or want to play only with me. Toward the end, I found a better balance of doing things with smaller groups and/or staying home from the daytime group hangs.
Angie was going through her book launch, and I was also still doing a bit of work throughout the trip, especially with a project in Taiwan, and we were stretched way too thin during the 2nd stop in Taiwan.
We were a bit shy about opting into more childcare because so many on the trip were devoting almost all their time to their kids, either via planned sabbaticals, being temporarily retired, being FIRE, or having one parent handle childcare during the week. But the system Angie and I had that “worked” for the first two years fell apart as the demands of a three-year-old taxed both of our systems a bit too much while we tried to slot in random work sessions throughout the week.
Reflections/what I’d do differently
It was amazing seeing the older kids thrive on this trip. It seems that kids aged 6-11 really loved being on this trip and would basically play with other kids non-stop when they met up. These parents had a lot more freedom to do other things or even do things with their kids. Ages five and under, I think the value of the “village” is harder to capture, and most of the work still falls on the parents. It did make me optimistic for trying something like this down the road, but I think we’d wait a few years. I’d probably also take a proper sabbatical, not just a kind of not-working but still doing stuff sabbatical.
I’d spend more time doing smaller one-off dinners with families and helping the kids connect much earlier, and I’d likely try to set up a more structured arrangement for help within the village for our daughter.
I’d do whatever I needed to do to find a consistent writing routine. I didn’t take this seriously enough. Lesson learned.
Overall, I’m really happy we went on the trip. It expanded my imagination for what I thought was possible, helped us find some new limits, and revealed some preferences. Mostly, I’m excited to cross paths with many of our new friends across the world in the future!
#5 We decreased our cost of living, and that feels nice
I try not to make decisions based on cost and have a principle that I live where I want to live and worry about the finances later. Despite this, it was very nice being outside of the US, where it felt like costs were accelerating on everything, and even though many people were doing financially well, everyone always seemed upset about how things were going.
The two big things that have been cheaper are housing and healthcare. Last year, we spent 45% less on housing, and this year, our housing costs will be about 30% lower. Even though Taipei is one of the most expensive cities to own property in the world, renting is still reasonable. On top of that, healthcare is essentially free in Taiwan, and they keep passing more and more subsidies for having children, driven by Taiwan being the fastest-growing country economically while having the lowest birth rate in the world. Certainly an interesting place to be.
Our current setup of housing, healthcare, and childcare is about 30-40% of what it would cost in the US, so that feels like a really nice thing to have as we have another kid and will continue to want some optionality to buy freedom.
#6 I found the lower limit of work I’d like to do
Since finishing Good Work in September 2024, I’ve had nothing close to a regular work practice or writing practice. My work days and time have been sporadic and random. I’ve probably averaged about 10-15 hours of focused work per week, with a couple of small stretches where it was closer to 25-30. I was living out the “leave money on the table” chapter in real time.
When I zoom all the way out, I’m happy with the trades I’ve made. I’m mostly trading opportunity and work satisfaction for family time. But over the past year, I’ve found myself a bit too fried and disconnected from myself after sucking it up and opting into more and more childcare. Since we were moving around so much, it was easier for me to just say, “I’ll step up and handle the gaps these two weeks” rather than put myself first and say, “You know what, I need some time for myself.”
I’ve been telling people that the ideal amount of parenting is not 100%, and the ideal amount of work is not 0%. The hard thing is figuring out what the right balance is between those two points for you and noticing when those needs shift. For the first two years, I could handle a lot of parenting and also work deeply on my writing at the same time. Sometime after my daughter turned two, I didn’t have much left to do the creative work, but I failed to admit this to myself. Being a parent has been incredibly humbling. Every month has brought a new little person with updated needs, preferences, interests, skills, and demands. And as she grew, I did too, convinced I could just keep handling more and more.
My curiosity drives a lot of this: What happens if I put family before work? I keep asking that question, and going in one direction always wins out over the other. I am happy about the results too: I’ve become much more resilient, caring, connected, and silly, and the dad that I always wanted to be. I am so much more ready for my second than I ever was with my first, and that feels really good.
But stepping back, I know that I need to put myself first a bit more in the coming years, too. To put my oxygen mask on first so I can go do my good work and come back recharged, rested, and inspired. I think any parent can relate to this challenge.
People always ask me to write a book about parenting, and I always tell them I have no idea what I’m doing.
The most confident parents seem to be the ones without kids, followed by those with 1-year-olds, and so on. The beauty of being a parent is that if you let it, it will break you open over and over again. I’m in the throes of letting that happen to me, and the best part is feeling all the joy that flows when you truly release yourself. I am definitely not going to write a book about parenting unless someone pays me a million dollars, but I can leave you with this: Parenting is a humbling, heartbreaking, and joyous journey, a potentially more direct spiritual path than psychedelics or meditation. It’s a journey that pushes you toward the edge of what you can handle over and over again, and if you let it happen to you, allows you to become more of who you are. I’m still in the throes of it all, and I’m not quite sure what will unfold next. But I am open and ready.
Two weeks in a row, nice. Am I back? Maybe? I think so? Let’s see.
I’ve been doing some form of public writing since 2015. I’ve somehow figured out how to hack a living doing things like writing books and launching premium art editions of my book. If you like what you read here, you’ll probably enjoy my books The Pathless Path and Good Work:
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Some things I endorse:
Readwise is offering 2 months free (I use it for book notes and reviewing highlights). Or two months free on
Readwise Reader, which I use for RSS reading and epub reading
Crowdhealth, an alternative to US health insurance that I’m still using while abroad
Postbridge: A social scheduling app created by a reader without crazy upcharges for more accounts
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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Thanks for this Paul! I loved this line: "My curiosity drives a lot of this: What happens if I put family before work?"
“Settled for now” really landed. I spent much of my twenties moving between cities and countries, including time in Taipei, and I’m still untangling the freedom of it from the way moving made it easy to postpone a consistent work practice. I appreciated your honesty about finding your lower limit for work. Staying put for a while can be an experiment too. Read your book about a year ago - loved it! (Actually quoted you in my round up on reflections on turning 30)