I'm pretty much convinced that the inflection point is "Director" at a FAANG or "VP" at a smaller company. Once you get to that point, it's pretty much impossible to fail downward. Worker bees rise up in level when they succeed (or the economy is good) and fall down in level when they fail (or the economy is bad). But, I've never heard of a Director or VP or anyone from the "executive class" getting a downgrade when moving jobs, regardless of performance and regardless of the economic environment. Once you pass that singularity, it's up, up, and away.
It's more about having the "fuck you" money. Once you reach this level, you typically have about $3-5M in various assets, so you don't have to work in order to keep paying your bills. You may want to work to buy that next supercar or yacht, but you don't have to.
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.
Importantly, having fuck you money means you can take outsized risk when you leap. To your point, your tolerance for worker bee work means you're not getting out of bed except for possible home runs. You're not going anywhere you're turning over Jira tickets, you're looking for the next score.
There are many people who reach the director level and then transition careers outside of tech, because they can no longer get hired at that level.
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.
I think another part of it is that there are many "bootlickers" that will do whatever it takes to keep that director floating, because they think or feel that director will get them promoted, give them a bonus, etc. The moment that director walks in, they are prepared.
I think this is mainly because such people are very career focused (and politically savvy to get to that point) and careful not to take a role that could even signal a step back. That and they typically will have enough financial security that they don't need to rush anything. "Lower level" folks are less likely to have both of these be true.
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.
I've worked with Surojit; he was an absolute superstar. He rose through the ranks on the basis of mountains of backbreaking and incredibly impactful work.
He also had a terrible reputation of being an arrogant prick. People hated working for him (or so I've been told). I've heard he made grown people cry.
None of that is true, so far as I know. I remember him as kind and considerate. That doesn't mean he wasn't demanding, but he was quite fair, and sensitive to the impact of his words and actions.
He was sr director when he left google first time, so more like 800k+
He was probably making > 1.5M in his second stint at google.
His big break was heading up mobile search ad revenue task force at the time mobile traffic was growing like crazy. Big oppty and he was up to the task.
It's hard to say he really succeeded at flipkart, google shopping, and coinbase. Each of those were 2 year or less stints.
BS in CS at Kharagput, something like a US T2 university
MS in CS at Buffalo, something like a T2 univeristy,
Spend some years at IBM and Oracle as a developer/senior developer 200k/year ?
MIT Sloan MBA T1 world class
PM/Senior PM at Symantec for a year 200-300k/year?
Head of Payment products India at Google, 8 years rising though the ranks 300-500k/year?, did an externship of 2 years at flipkart as SVP
Then back to google as a VP 500-1.5MM/year?
CPO at coinbase made 150 million.
It looks like he moved around, leveraging his title to get senior roles between start-up and well-established companies:
PM at small company to PM at big company,
Head of product at big company to SVP at startup
SVP at startup to VP at big company
VP of big company to C-suite at startup pre-IPO
Most of all, he got in on the crypto gravy train right in time for his options to balloon