> Why is he still working and not in retirement?

This should not be a question. It is none of your business.

How about letting the person asking the question take a stance on that instead of you being offended from the side-line? I think it might be a very important piece of information to figure out a strategy going forward.

I am not offended, not by a long shot but I would be if someone asked me similar question.

He's passionate about engineering and has a lot of energy which is why he's still working and wants to continue. I think his focus is on identity, worked for a few years before this as a support engineer for an enterprise software company which ended up moving to a different state (he liked that job a lot more). But he's had a spotty work history, taking up engineering late in life and starting his own IT company which shut down ~15 years ago.

From what you've told so far, I think he should just simply look for another job. If it says DevOps, SAFe, Agile or something like that in the title or job description, then chances are the company has unfortunately been swindled by these snake oil salesmen and it will be hard to find time for good engineering.

There can't really be a shortage for more support engineers if he likes that, but if he wants to do more core engineering then of course go for that. Most of the big enterprises should have room for him in many different departments and he might be comfortable and safe.

As for concrete advice: Just go looking for jobs and weigh pros and cons. You can do it on his behalf and bring a few to him for discussion.

Don't be pushy if he's not into the idea and just feels like complaining a bit. Sometimes all a person needs is a bit of acknowledgement and not a solution.