There's that old saying: Help is totally unhelpful when it's not requested. That certainly applies to our aging colleagues, neighbors and friends who seem to have decided to just give up on working. They have stopped looking for a job or ways to bring in income running a small business. The big mistake we can make is butting in. I know.
In the senior citizen complex where I live there are a growing number of unemployed professionals and artists who say they want to work. However, their behavior indicates otherwise. Talking about resuming working probably makes them feel better. However, we step on an emotional landmine if we begin to move into that space with recommendations and a pep talk on how they can find employment or new business. The reality is that they are "done." Their careers are over. And that's that.
Once we realize that, we probably don't want to listen to their chatter. Fine. Then we have to figure out a polite way of veering out of that force field. But no longer will we be investing ourselves in something that will wind up frustrating both parties.