[thekevinscott]

I quit my job in 2009 and moved from place-to-place for about three years while freelancing. Spent about 6 months each in Austin, Portland, Chicago, and Buenos Aires, with shorter excursions elsewhere (Santiago, Berlin).

By the end of the three years I'd lost the travel bug and longed to be more settled in one location. With about a decade of hindsight now, I can say:

- Those years traveling were a highlight of my life. I often reflect on them and reference them, in a probably-very-annoying-to-my-friends way.

- Traveling gave me a ridiculous amount of self-confidence. Having to land in a new city, make a whole new set of friends, learn the rhythms, (in some cases) learn enough of a new language to get by, was challenging but immensely empowering. Obviously there were deep, lonely periods as well, but the good and the bad go together.

- In a roundabout way, it was a boon for my career. Moving every 6 months in 2010 basically meant I had to freelance, which forced me to learn a whole new skillset of selling, which in turn led me down a path of entrepreneurship. It also led me down some unexpected paths, whether it was folks I met at a coworking space or learning about the Microconf community.

I wouldn't do it now, but I'm so glad I did it back then.

[supernovae]

I'm Curious what the reasons you wouldn't do it now are? I'm probably older - i'm in mid 40s and kids are of that age they don't care what I do so i'm looking at possibly just going remote and on the road for 4-6 months - still working the job but curious what it is you value/appreciate now that you maybe didn't have while on the road/traveling.

It's always one of those things I don't want to NOT try it, but i'd rather be grounded in the reality vs think its gonna be all roses :)

[thekevinscott]

Well, I suppose I have to directly contradict myself by saying we moved down to the South for the past couple months to escape the winter, and it's been glorious.

The biggest barrier is my partner's job not being very remote-friendly, so outside of pandemic times, long stretches of digital nomad-ism are probably not realistic for us as a unit. I'm also not sure what traveling as a pair, or as a family, would be like -- I imagine one person's paradise could easily be another person's nightmare.

I also got the impression that it's easier to live the "traveler's" lifestyle when you're younger, in that you've got more folks amenable to meeting you, hanging out, having more free time. That may have changed with increasing digital infrastructure, but things like hostels and couch surfing I found to be very geared towards a younger clientele (even as a mid-20s fellow, I sometimes felt too old!)

That all said, if you're in a place where you can do it, I think you should! 4-6 months is not that long and if you're in a position where you can try it, the worst that happens is you can say you tried it and didn't like it.