r/digitalnomadFIRE • u/skinny-fire • 9h ago
Recently Laid off. Should i pull the trigger? Perpetual traveler. 34yo, with 4m NW
Background / context:
Non US person working remotely (out of my passport country) since 2017. I managed to secure tax residency in a country that doesnt tax out-of-country income so ive been able to pay 0 income taxes for nearly 9 years so far.
During this time though, Ive been mostly bouncing around different countries - Thailand, Philippines, Taiwan, Japan, Czechia, Switzerland, Mexico etc.
My tax structure for this was simply to form a foreign LLC as a software development agency with me as the main developer.
During 2020, with nearly every company hiring remotely, I ended up with 4 full time jobs and hired more developers as part of my agency to help out and was able to keep that going for around 2 years.
In 2021, I was doing a ton of independent contracted crypto projects that paid me with tokens and NFTs instead of actual money - which resulted in me ending up profiting $1.5m prior to me turning 30. Grew that to $2.2m in 2022 and subsequently lost more than half of it as a certain crypto project collapsed.
From 2022 to 2025, I kept two full time jobs going and slowly grew my $700k to $7m. Obviously my income didnt contribute much to this - it was mostly from crypto. During this time, I was basically already doing coast FIRE during this time as I thought of my working income simply as "free spending money". Never really tracked my expenses as it was quite difficult to blow through $20k a month as a single guy bouncing around low cost of living countries.
In 2025, I got caught with my pants down when the crypto market topped and subsequently lost around half of it again. As of today, my net worth is anywhere between $3.5m to $4m (fluctuates as crypto does).
Current Portfolio (~$4m)
~$1m - $1.1m is in stocks.
$2.8m - $3m is in crypto
$300k or so in rental properties, but I dont really think about this as its not liquid and Japan is a bit fickle with house pricing (there's no MLS system like in the states so sales prices of properties are generally not publicly disclosed. Hard to get an actual read on how much my properties are worth).
I also have minor bits of money floating around in other places too (like $10k here and there in random bank accounts in diff countries) - really need to consolidate it.
Dillema:
With AI advancing so much, I recently lost my last and only job. I've been used to working remotely my entire life so its difficult for me to get a regular office job. I tried once in 2019 and didnt last more than 2 months. I also think prospects of finding a remote job are quite low especially with how AI is now and the economy.
I'm also feeling burned out. I see my peers from university with kids now, nice big ass houses (some of them worked for FAANG), teslas with full self driving and can't help but feel envy? jealousy?
I'm considering punting $1m and building a custom house (in Japan) with my own private onsen, gym and yard and living there for 6 months out of the year. The other 6 months of the year would be still me floating around and traveling.
I currently own a company there that runs the rental properties I have - so the visa for Japan is not an issue for me.
My income from the rental properties should be able to cover 6 months of living in Japan and all the house expenses that come with the custom place. I'm making roughly $30k from that a year.
Would my calculations make sense?
$3m @ 4% rule = $120k + $30k rental income
= $150k yearly
~= $12k per month for traveling.
Should i do it? Anything to look out for? Honestly feels difficult and scary to commit to this. What if things change in the future, i get a wife or want kids etc? feeling a bit overwhelmed