Remember that in the "old days", computers were very expensive and the selection of operating system and languages was almost always made by business executives

Remember that in the "old days", computers were very expensive and the selection of operating system and languages was almost always made by business executives based on money and trade press. Workers would typically have NO say in what language or systems they would use during their "day job" unless they changed jobs...and in those days, if one changed jobs too often, they were considered a risk. As if that didn't limit one's ability to learn new languages, employers would also only accept workers who were not experienced in their desired language/system during a very limited window, generally just after mass adoption, for example, during FORTRAN to C or Ada, TurboPascal to Delphi to Visual Basic, C to C++, etc.) so, for example, an ace FORTRAN programmer wouldn't get the chance to jump anywhere if they waited until, say 1990, to do so. By the same token, as people age, with more mouths to feed and more bills to pay, they become risk averse and many would avoid such language transitions altogether and in doing so, would render themselves obsolete as their unchosen language died. Still others would bet the farm and change jobs frequently, but wind up with dead-ends (Ada, FoxPro, TurboPascal, etc.) In the world of today, one can buy a computer for $40/mo that runs every language ever written (one way or another), but that just wasn't the case back in the day. When an old Boomer says they did all the right things by learning new languages, they mean they took the risks they were (quite unfairly) expected to take (just to try and preserve their occupation), but in some way, they couldn't always keep up with industry changes. (Combine This with H1B-fraud and C-suite wage theft like https://en.wikipedia.org/wiki/High-Tech_Employee_Antitrust_Litigation https://en.wikipedia.org/wiki/High-Tech_Employee_Antitrust_L... and you have a retirement disaster decades in the making.) To the 65 year old, you're not that old for a non-physical occupation (look at Woz) and when I started in this business 40+ years ago (tho still not yet old enough to qualify for the senior menu at Dennys), it was common to find guys your age around teaching us younglings --I learned a lot from them, miss them and I have sincere pity for the post-Y2K generations that lost that after the elders were forever purged (first to be RIF'ed and all at once as the dot-com bubble crashed demand for tech from 2001-2006). From following some of the elders through all of that, I know you're going to want to avoid head hunters, focus on marketing yourself to small companies and approach future work assignments as a LOYAL AND DEPENDABLE partner not just a body showing up to a "job". Pay attention to your shoes. Not fair that you have to hustle more as you get older, but nobody ever promised you fairness. (Also, I strongly recommend against investing in another line of business at 65, as I've seen that not work out a lot.) Lastly, don't listen to the critical voices on here and similar sites! [ https://youtu.be/fLVN05Jl6wA https://youtu.be/fLVN05Jl6wA ]