I probably shouldn’t necropost, but I thought that the folks who commented on this thread might be interested in an update. In truth, it isn’t a sad tale. The dude in question has been occasionally employed, more typically (as currently) unemployed, but has found a way to manage without cash infusions from me. I talk to him about every 3 months or so, but he seems to have accepted that my teat has run dry. At the same time, he is living exactly the life he wants. He has published a book that will never have significant commercial success, but which was meaningful in its own way, and he has been working on another project. He lives in what I would consider poverty, but he seems ok with that. Very much living in the moment. Makes me wonder sometimes what I am doing still working with a seven figure net worth.
So what is the lesson I have learned as of today? People are pretty resilient? Have a little more remove from people who are trying to manipulate me? Pause and say, “well, I’ll need to think about that?” “I’m not willing to do X, but I will do Y.” Or just that I really shouldn’t think that someone else approaches situations the way I would, at all. Maybe all of the above. As The Doors sang years ago, “people are strange.”