Thoughts on Structuring a Nomadic Year

It’s been a muggy and rainy week in Puerto Rico, but it helped me with my regret of not spending more time at the beach.  I did discover some new restaurants, had a bit of wine, a new beach, and I remain surprised at how many interesting things in San Juan there are that I have no idea about.  I’ve been considering doing a more thorough inspection of the city.  Comparing all of the beaches (I’ve only been to a few), good restaurants (so many sitting in my recommendation queue), activities, etc.  At some point I’ll get around to creating an Evernote/Gdoc with good notes.


This past week was highlighted by me still swimming in the currents of market volatility and becoming at peace with it.  One of the parameters in a trading model of mine wasn’t updating like I expected it would (it was updating correctly based on the formula, but the result was different than what I wanted/expected), and it caused some stress when I started trading too much.  It wasn’t hard to fix, but it was annoying.  Outside of putting in the bare minimum amount of maintenance time though, I took the week off from trading activities as much as I could.  No new research, no coding, and disconnecting mentally as often as possible.  I have some major projects to work on, but nothing time sensitive that I couldn’t put on hold a little longer.  As I write this I’m feeling pretty refreshed and looking forward to doing some logistical work tomorrow.


I went to Humidity Athlete Recovery Day Spa in San Juan twice this past week.  I forgot that going to a spa is such a simple mood-boosting hack.  Even though it’s 90 degrees outside the wood and rock smell of the sauna was very relaxing, the cold pool helpful, and the electric air compression leg/arm wraps they had were awesome.  I used to go to Korean and regular spas in LA a decent amount, but I forgot about that after moving.


I started living a nomadic life around 4 years ago (it feels much longer), although I did move to the Bay Area for a year, and I currently live in Puerto Rico.  I still spend about 4-5 months a year abroad though, so I would say I’m still in that world even though I have a “home”.  I often think about what my ideal nomadic life would be like, and I thought I would share it.


There’s the obvious glamour of living in exotic warm countries, in much nicer housing, for a lot less money than you’d pay in the US.  You meet interesting attractive people, and can have as much/little fun as you want.  You also learn a lot about the world and yourself, and get some perspective/appreciation for how lucky we are to be able to live like this.


The downsides of nomad life are large too though, and hard to understand until you experience them first hand.  The three biggest ones I would say are: the loneliness of being far away from your long-term friends/losing your local friends every time you move, it can be expensive if you don’t know how to scour local rental rates/fly too frequently, it’s hard to get any work done when you’re traveling a lot/ in a new place you want to explore.


It’s common for me to meet people who are burnt out living what on paper is an “ideal life” in Thailand, Bali, etc.  Eventually you can’t “out fun” having some structure and meaning in your life, and having people you care about to share everything with.  It’s also stressful constantly finding housing, especially in a country you’ve never been, especially if you don’t want to spend five times the normal rate.


With that said I have a rough idea of my current ideal nomad situation.  I think people would be happiest if they have a place they can call home or home base, for at least 6 months a year.  For me it’s closer to 7-8 months, and San Juan, Puerto Rico is it for me.  I’d be pretty happy in Medellin, Costa Rica, Bali, or Chiang Mai though as well.  San Juan isn’t cheap, but with the tax benefits for Americans it becomes an incredible value, as well as being a beautiful, friendly, well-balanced city with easy access to the eastern US.


The options for having a home base are owning/renting and turning it into a storage unit while you’re gone each year essentially paying double rent (paying for your travel place as well), trying to Airbnb it, or signing 6-8 month contracts, and having to look for places every time you come back.  None of these are great, but it’s a lot less painful than moving every 2-3 months year round.  I think if you find a good deal on a home base in Bali/Thailand it can make sense to sign a year lease at a much cheaper rate, and leave it empty when you’re gone.  It might be cheaper, you can let friends stay while you’re gone, and you don’t have to deal with the hassle of finding something when you’re back.  I have a unique situation in that my apartment in San Juan was an Airbnb managed by a company, and last year they let me leave for a few months while they put it back up on Airbnb, and then I moved back in at the end of my travels.  It feels weird to know that strangers have been living in my apartment while I’m gone, but then I remember that every Airbnb/hotel I stay in that’s the case.


As far as travel I think two places a year (outside of my home base) is great but not overwhelming.  Going for less than 6 weeks is annoying unless you’re staying with friends and know a city.  2 and 2 months, or 1.5/2.5 for me is good.  Summer in San Juan gets really hot and humid, so that’s an ideal time for me to go.  May/June in Europe (Stockholm to see my girlfriend’s family/friends) and July-October in Bali is a great combo.  I’m in each part of the world during the year making it easy to see friends, or for them to visit me somewhere fun.  I also get a few different cultures to keep me stimulated, but I can also have all of the things that I like to each of these locations (training, healthy food, coffee, co-working).  Going to places where you’ve been also helps alleviate research, as well as providing some immediate local friends.


I realize there’s a lot of exceptions and nuances for other people, but I’ll leave it at that as I don’t have the interest to write a digital nomad book.  Some structure makes nomading a lot more enjoyable for me.


I’ll write more about some recent books I enjoyed next week.  I am working through a good and free meditation course online though that I would recommend:


The website is cheesy and comes off as an infomercial where it feels like they are setting you up to extract a lot from your credit card, but the course is genuinely free and good.  I found out about it because I’ve been reading material from Shinzen Young, one of the people involved in it.  He has some interesting takes on different meditation techniques that have been helpful to me lately.


With that I’m back to relaxing before I get back to work tomorrow.  Leaving you uncharacteristically with a picture of me two weeks in a row now, featuring my girlfriend and some of her friends before we went for dinner in San Juan.



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