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I don't have any clear answers on whether I recommend it, I'm still deciding on that for myself. But I'll give you my thoughts.
The obvious best is getting a way cheaper cost of living. With my middle class American salary, I feel rich in a lot of foreign countries. Like 1/2, 1/4, or even less than what it would be in the US, depending on what you're willing to tolerate. I also really enjoy being able to get away from some of the stuff that's always bugged me about the US- suburban sprawl, health insurance, red-blue politics, enshittified apps for everything, and lack of good nightlife. Those are just my own preferences, but nice thing about digital nomading is you can kind of pick and choose what lifestyle and culture you want. Of course, every place has its downsides, and you start to see those more once your there.
Worst thing is that I can never stay for as long as I want, because of visa issues. Plus being an obvious foreigner with no permanent ties to the community, it makes you feel like weird and adds a lot of hastle to even simple things, like getting mail delivered. It's hard to stick to a regular diet or exercise plan or join clubs. I'm hoping to figure out a way to stay more permanently, but a lot of countries don't have good visa options for that, or only for older people.
Country-wise it depends a lot on which city and neighborhood you're in, but I really enjoyed my time in Mexico, Taiwan, and Japan. All 3 managed to hit the sweet spot for me of feeling comfortable enough to relax, significantly cheaper than the US, and interesting enough to find fun things to do as a random foreign single guy. It also helped a lot being able to speak some Spanish and Japanese. I did not enjoy my time in Southeast Asia where I couldn't understand anything at all, and I thought Western Europe just felt too similar to America to be worth the hassle.
Thanks for the reply! Sounds like overall it's kinda fraught with issues. Once you find a place you actually like a lot, you can't stay for long. And you should know the language before you arrive. I can imagine feeling alienated if you don't understand what anyone is saying. Japan is tempting, even for solo travel, but I would have to either learn some Japanese or be prepared to not be able to communicate with anyone beyond extremely basic words.
I'm not looking to be a perma-nomad or anything, but I do want a place where I can stay for ~3 months per year with a decent climate.
The thing about language learning, especially a non-European language like Japanese, is that it's a never-ending process. It's not like you hit some threshold and suddenly understand everything effortlesslly. It's a continuous grind to learn new words, new grammer, and improve on the basics. You can get by in any country with English, hand gestures, and phone translation, but it's not very comfortable. It's one thing to be able to do simple things like order food in a restaurant or follow transit directions. It's a whole other level to do the things that I want to do when I'm actually living somewhere- take a class, read a book, or keep up with people's jokes. Hardest thing of all is being in a group conversation and trying to understand what multiple people are saying, while also thinking of stuff to say myself. Even if I'm fast enough for the conversation, I might just not know the thing they're talking about, like if they're referencing some random local celebrity.
On the plus side, being an obvious foreigner who speaks English does have some advantages. You'll naturally meet more curious, intellectual type people who want to practice English and learn about other countries, as well as other foreigners travelling. And if you're like me and you tend to over-intellectualize everything, speaking in a foreign language can force you to just be blunt and spit it out in plain, simple words- because that's all I have!
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