I can appreciate the story - it's a paean to a lost world when we didn't need to be competitive. The thing is, money provides more power for the fisherman, which he would need if his environment changed:
-rebuilding after an earthquake
-fleeing if the local government goes bad
-dealing with a crash in tuna price
We all still live in a competitive environment. Hunter-gatherers were replaced by massively-reproducing (but probably unhappy & unhealthy) farmers. In the example, fishing represents pure surplus value, produced from nothing - and in economic situations like that, producing less than others means you'll eventually be out-competed and replaced.
In reality the same tragedy of the commons applies to fishing, and we haven't solved it there either.
Until competition is restrained, we've gotta compete. Individuals can opt out but they're just removing their traces from the future - those left will still be struggling until we have a way to globally eliminate environments which force people to be maximizers. And in a big universe, it's uncertain whether we can ever really control enough to be able to relax. It may even be computationally impossible to really stop the continuous evolution of competition in how we live life
While I don't have access to Dillon's finances, his personal site http://www.backplane.com gives some hints:
BEST Internet was an incredible successs successs [sic]
These days most of my attention is focused on the The DragonFly Project
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He isn't the only one, many open source developers contribute because they want to do it and not expecting any monetary compensation.
Matthew Dillon doesn't need to work but keeps working on DragonFlyBSD.
Also it is possible to live and work as in retirement http://www.noogenesis.com/pineapple/fisherman.html