Another possibility is we understand the value of compounding, so we let our investments grow while W-2 income meets daily living expenses. After a decade or two, the investments return more than flying and work becomes optional. A work optional WBA or WBB lifestyle isn't a bad place to be. Health benefits, travel benefits and 5 weeks of vacation just for fogging a mirror is a great start to the year. Add on 6-9 days of work for the month and it's easy to see why someone with an 8 figure net worth still comes to work. PIlots like that aren't as rare as you think. I've met plenty over the years.