scoreandmore parent
I met a youngster on Boca del Toro island in Panama a decade or so ago. I was about to be fired from my FAANG job so I used up years and years of vacation for one big trip before I was let go. We hung out for a few days while I was there (I don’t recommend the place at all btw). He cashed out from early twitter and was setting up surf schools all of the world. All he did was travel, surf, drink, and fuck. I’m still angry that laughed at all the dumb startups in the late 2000s instead of joining them. But this guy did what you’re suggesting, and I think there are many more unknown techbros who did it too.
Setting up an international chain of surf schools actually sounds quite ambitious and stressful, though.
I imagine stress is relative to risk. I’d hope someone who has retirement on lock wouldn’t risk that for a side project.
Though for me the risk of the shops failing and people being out of a job would still stress me heh