So, if you are out of luck, you postpone that $5M waterfront summer home purchase, go sit on some board for symbolic money, sniff around, and eventually join some hot startup when you and your buddies found another investor cow to milk.
Not having to commit your time to a shitty offer in order to pay your bills right now makes a killing.
This is especially common during a downturn, when there's less money to go around for people who are "inspiring", but can't "roll up their sleeves" or earn the respect of those who do.
Depending on how long you've been in the industry, it might be because your sample size falls within the anomalous period of 2001-2022. Expect to see a bunch of ex-tech directors opening bakeries, breweries, consulting/"life-coaching" practices, etc.
I don't think I'd call it falling downwards, more like surfing tangentially. It's still a pretty comfortable and fulfilling life, but I wouldn't describe it as up, up & away.
[edit] this is pretty hard to disambiguate from the "fuck you money" types described by a sibling commenter, superficially, but there is a wide distribution of net worths in this group.
There's going to be a whole lot of people who peak with some fancy-sounding title at a no-name company. Then they fade into a vaguely-comfortable (but definitely not rich) obscurity where they can't fully retire — but they sort of drift along with occasional consulting gigs, or writing a niche Substack, or getting really into baking sourdough bread, or some other such nihilistic affectations.
In the grand scheme of things, it still beats having to get a real job.
Andrew Fastow, former CFO of Enron, became a document review clerk after serving his jail sentence. But five years later he became something called a "Principal" for an analytics company called KeenCorp.