Well, really, there is no binary choice "work for money" and "don't work at all", but rather a huge spectrum: "work at a shitty job", "work at an awesome job",

Well, really, there is no binary choice "work for money" and "don't work at all", but rather a huge spectrum: "work at a shitty job", "work at an awesome job", "be a contractor and take sabbaticals every half of a year", "have a small stream of passive income and cool freelance gigs",... Therefore limiting your attention to the final stage which is quite hard to achieve, it's quite unoptimal.