Almost two decades ago, while I was in a bit of a funk about the not-very-interesting, heavily corporatized thing the software industry has become [2] I read th

Almost two decades ago, while I was in a bit of a funk about the not-very-interesting, heavily corporatized thing the software industry has become [2] I read the book "Vagabounding" [1]. It talks about doing exactly what you're describing and it sounds great, but then, if you're like me, you start worrying about your long term, and, for example, eventual medical costs and so on. Like many things, it sounds great until you consider downside risk. [1] https://www.goodreads.com/book/show/100247.Vagabonding https://www.goodreads.com/book/show/100247.Vagabonding [2] Essentially, I was very, very familiar with the 1970s and especially the 1980s Valley since parts of my extended family were directly involved, and I'd been looking forward to it and all of the excitement around it. The 2000s+ experience of the valley is far, far from that era for people who love technology, building things, excitement, etc.