I've worked for a few bosses/ceos like this. Far more interested in being seen as someone with a particular title or company and far less interested in what it takes to actually make that worth something.
I reached a point--somewhat older than that--when I didn't have a real job any longer, but nobody seemed in a big hurry to get rid of me, and they were paying me pretty well. I made it through a small layoff though I wouldn't have minded the good severance. I might have hung around in different circumstances but figured I should optimize the payout up to a point and wasn't really interested in heading somewhere new.
Maybe. It's very situational. Beyond the spreadsheets for a given location, there are times in your life when you want to be able to pickup and move fairly easily and there are times when you want to be able to put down roots and be in a pretty stable situation that lets you tailor things.
"Putting down roots" is the wrong way to look at it. You have to ask yourself if you're certain that you will be in one area for a long time. Everyone wants roots in LA or NYC, many of them wash out.
I did "reasonably" well for a couple decades and then I did, if not spectacularly, well for a decade+ that certainly set me up for retirement. And I might have even retired earlier absent COVIVD. Not spectacular sums but certainly reasonable amounts given owning a house and modest travel sums.
The other thing I see is that people nearish retirement age and are comfortable, who might have cruised on for a few years, are pretty much going: now is probably the time. Maybe do some consulting though that's tight right now. So, maybe not optimal, but why stay in a non-ideal situation?
I do know various people who left a job with a former employer because they weren't happy and seemingly landed fine AFAIK. I mostly stuck things out for a bit because I was mostly retiring. Otherwise, I'd probably have done the same even if the end-result was retiring a bit early.
Probably not uncommon. My final year at my last employer post re-organization and other changes was cold-hearted money extraction for (generously) part-time work. I was sort of disappointed I didn't get a package when they laid a fair number of people I worked with off. But I took a hard look at my vacation balances, upcoming holidays, RSU vesting, etc. and decided to coast for about the next year which, as it turned out, was just about the point it would have been difficult to continue on with no real job not that I would have wanted to.
On the other hand, you have to guard against being that person who is in a perpetual state of "Benn there, done that. Didn't work the last 5 times we tried it." Because sometimes the circumstances/market/tech ecosystem genuinely are different.
The key us in understanding why the previous times failed. What constraints existed then, which possibly no longer exist now.
Projects fail for many reasons. Technical, market, capital, time and so on. But things change. Building an add-on for electric cars would likely fail 20 years ago, again 10 years ago. But now? Or 10 years from now?
Only by -really- understanding what caused a project to fail can you determine if that barrier is no longer in place. Which means you can try again, and potentially find the next barrier or success.
I'm a bit hesitant to describe $NEW_CONCEPT/TECH as just $OLD_CONCEPT/TECH. Echoes of older things in a new context can really amount to something different. Yes, VMware didn't create the idea of virtualization and Docker et al didn't create containerization but the results were pretty novel.
I'd rather say that good ideas keep on returning, no matter whether they are remembered or getting reinvented.
It's not that those who reapplied the old concept in new circumstances are not innovators; they are! Much like the guy who rearranged the well known thread, needle, and needle eye and invented the sewing machine, completely transforming the whole industry.
But seeing the old idea resurfacing again (and again) in a new form gives you that feeling of a wheel being reinvented, in a newer and usually better form, but still very recognizable.
