Looking for a Job Is Tough

In my case, the process became so awful, humiliating, and hostile, I just gave up, and retired, ten years before I had planned. I’m very fortunate, that I could afford it. I now develop software for free, for outfits that can’t afford people like me.

It’s tough, but looking for work after 50, especially when pivoting from management, back to IC, is unbearable. My heart goes out to those without the means to walk away. I think some companies missed out, but I am under no illusion that I’m missed. I doubt they had any regrets in passing me up.

In my case, it was probably the best thing that ever happened to me. I left a lot of money on the table, but I have been happier than I ever dreamed, while working twice as hard as I ever did, when I was getting paid for it.

I suspect we will see startup founders trending older if it isn't already happening. Companies stuck in the old way of thinking that older is slower will probably be disrupted in the next recession.

Anecdotally, I think it already is. Part of it is simply because the younger you are, the less risk you can take with the cost of housing the way that it is. Older people/Millenials often have housing security and can take more risks this way, plus the other factors you raised.

Can't speak to whether that's universally true, but it's something I've been seeing: including people in their late 30s to mid 40s leaving cushy well paying corporate jobs to try founder life: they have big nest eggs from said previous jobs, so why not!