If you're interested in doing something like this, you could join the Vic Maui race: https://www.vicmaui.org/
https://arachnoid.com/sailbook/index.html
I read it years ago and still think of it from time to time. It's a great read.
HN submission:
https://news.ycombinator.com/item?id=901072
His site never gets much love from HN:
https://news.ycombinator.com/from?site=arachnoid.com
If you're interested in doing something like this, you could join the Vic Maui race: https://www.vicmaui.org/