My latest views on the subject of this thread.
1) Stay completely away from big companies with their HR departments.
The policy against hiring older workers is really not all that stupid, even if it is discriminatory and illegal. The problem is cultural fit. Big companies have rigid reporting structures and don't want problems in the chain of command. A person reporting to someone 20 years their junior could be a problem. Also, the broader culture stereotypes older people as being slower and possibly trespassing in a space (a workplace) where they don't belong. Being present in such an environment can be very unpleasant for the older worker.
2) That leaves smaller companies.
This is where an older worker wants to look for a job. It's best to figure out how specifically you can add value and what specifically the company's problem is and what they are looking for. Personally, I've never done this kind of research on a company, but it sounds like a reasonable thing to do.
3) If you get an interview, take a Shark Tank approach to pitching yourself.
Notice how the sharks want proof they will get their money back. "What are your current sales?" is the first question they ask. It proves that a person can service the market they say they can. From there on out in a Shark Tank interview it depends on how the person comes across. Are they enthusiastic? Does the product make sense? Is the person likable?
How would an older, unemployed, older worker prove sales? Well, maybe you can't prove sales if you are unemployed in the sense someone is paying you a salary, but you can prove a user base, even if it's unpaid.
You can do that through web and mobile apps which people are using. Or one might provide useful free information and build a following and then monetize it as this person has done:
http://www.buydonthold.com/category/blog/.
I really like Masonson and believe in his strategy (and have made a little money using it). The general idea is that you look at a list of high-performing ETFs, which he maintains here:
https://www.etfscreen.com/buydonthold/bdh-decision-page.php and then buy and sell them based on an overall market momentum change which is indicated by (I think, currently 3) signals which he tracks.
Masonson published a book about his "Buy, Don't Hold" strategy and then published his blog for free for many years. It's still free, but now he's asking for $20/year for special emailings to subscribers. A service which I readily signed up for.
What stands out in my mind about Masonson is the goodwill he generates. He comes across as someone who is genuinely altruistic. I don't think I'm naive in this regard. As I said, for many years he did a lot of work to publish his blog that *may* help people invest more wisely. I say, *may* because I know that modern portfolio theory generally is against market timing.