Lots of diseases can affect your ability to work, as Malcat has said. . I read that roughly 1 million people have long-Covid that is preventing them from holding a job.
Let's frame this though.
It's still VERY different being unexpectedly disabled and financially crunched because of it vs being comfortably retired and having to adapt to a new set of limitations.
I really cannot overstate how radically different the reality of pursuing paid projects is when you don't really need the money any time soon and can invest in support and training if you want to.
If your friends had ample resources, they could invest in interview coaches, head hunters, take networking courses, level up their skills, or fully retrain.
Other than interview coaches, all 3 did some of those activities and certainly at the beginning of the process they did have ample resources.
I think I see the disconnect. For you, "pursuing paid projects, learning new employable skills" is an activity that I think you enjoy. As I said retirement is all about having more time to do stuff I want to do, having the money to pay people to do stuff I hate, and not increasing the amount of time doing I activities I tolerate. For me, pursuing paid projects... falls in the tolerate to hate activity. This is why I'd rather OMY at a a well-paid job that was in the tolerate or above category.
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All of these folks had by MMM standards accumulated enough for a lean retirement, but only Jack was successful in maintaining it. After watching probably a 100 of these stories on PBS, and reading an equal number in WaPo and the WSJ. I can nit pick their money management skills, but in most cases watching their struggles to find a job as unemployed older Americans. I really say there but the grace of god, go I.
Now wait a minute. You can't say "by MMM standards accumulated enough for a lean retirement", you're missing half the equation. If their expenses were higher than 3%-4% of their NW then it doesn't matter if they have $1M, $2M or more, they didn't have enough to successfully RE. They HAD to get a job. Or they needed to make some serious lifestyle changes (like move) and they failed because they didn't do either. I don't think that's "nitpicking their money management skills".
But, to your point, those in the 50+ age bracket often don't fair well after a layoff. 2008 was what brought me to the FIRE movement. I was still early in my career at mega-corp and I saw a bunch of mid-level managers in conference rooms crying. They were laid off. Many of them had large mortgages to worry about, car loans and other debts. Over the next years I would say half of them successfully landed another similar position. Others remained unemployed or underemployed. My DH and I watched this and set a goal to be financial independent by age 50. Just in case.
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My apologies, I wasn't clear. The grace of God comments was not referring to my friends, it was referring to the 100 or so older folks I saw profiled in the media during the Great Recession. IIRC, statistically, around 2/3 of white collar workers over 50 ended up worse and 1/3 better. So similar to your former co-workers This was through 2012. A 50-year getting laid after 2012, I'm sure faired much better due to the great job market.
As far as my friends go, Jack did transition to an early retirement successfully, once he hit 59, the IRA penalties were eliminated. The renter's income was a huge help and so was social security. Social Security provides a majority of income for more than 50% of seniors. It is much less than 1/2 for Jack. He would have preferred working longer at decent pay job to have a bigger cushion and a better lifestyle. He primarily just had bad timing
Jill, mostly made bad investment choices (too much stock market exposure, keeping the house too long and was too generous with her children.
Bill, made one disastrous choice, not diversifying, but other than that lived very frugally