I think the reason you are even able(read afford) to move to Hawaii is because you went through a couple of CTO/VP Eng positions, with traditional increasing stress.
Any American citizen can move to Hawaii anytime they like. It's not terribly hard to do, especially with a high demand skill that lets you find work anywhere, globally, like being a software engineer.
I think the point is that if he kept programming (i.e. doing what he enjoyed) rather than taking the CTO/VP positions he might not have needed a break in Hawaii to de-stress.