You lost me a little on this comment.

Regarding transactional point of view, are you suggesting this is a problem? Up until my mid 30's I wasn't this way (religious, turn the other cheek). I have always been the guy that tries hard to make everyone around me a little bit better. I value kindness, empathy, generosity. So much so that it led to enabling systemic bad behavior and high drama. People love talking to me, I'm a good listener, I make them feel interesting (different people are very interesting to me, I used to consider myself a punk). So I've got that down. Problem is I can do that without having to reveal anything of myself, no skin in the game. It's all about hiding in plain sight. Not helping me and my trust situation.

Similar to what you talked about with your wife, there was close to zero meaningful reciprocation in my life, and that led to major problems. I learned I had to start expecting some form of reciprocation from people. I don't think I'm asking for much now (as I said I'm pretty much taken care of for the rest of my life), but I am asking for something. I guess what I'm just asking for in return is having a low drama good time and that my generosity doesn't get taken advantage of? That to me is a good start for building real trust, or am I wrong? So I see learning to expect reciprocity as personal growth on my part, not a problem to overcome. Thoughts?

I do find my friendships valuable, and I sweat their loss. However most of the new ones continue to fail the reciprocity test. For example, I've found the bar/boat crowd to be mostly people that are combinations of liars, cheaters, and alcoholics (and hidden drug use). It's fun at first, and they are all very interesting, but these really aren't the kind of people that I should be building a friendship network from, as the people they've "vetted" aren't any better. So I end up just being the person who takes them out and buys them booze. They call me in the middle of the night when they are drunk and need to be picked up, etc. I don't cut ties quickly enough, and I'm working on cutting ties quicker as you suggested. Are you suggesting I'm seeing this situation all wrong? Are these the people I should be learning to trust and investing in more?

I'm terrible at networking, I've just not needed it. I've just doubled down on independence and hard work and it's always worked out in my career. This is where I got lucky, working for really good people. As they've climbed the ladder they brought me with them. So this is another outside idea that my gut says you're right, I have to give this a try. Not good at it, it's the trust thing, they're all attack vectors. But I'll work on getting better.

As far as "authentically sharing things about myself", most people don't understand where I come from and how I think, so I tend to reach them where they are. I haven't found anyone I can truly be myself around. I mean if you want a female partner in your life you have to find a way to enjoy a certain amount of chick flicks and cooking together. Fewer philosophy discussions, science discussions, technology discussions. It's why I've been focusing on boating so much, I really enjoy the sun/water and it's something that I have in common with a lot of normal people so I figure that increases my odds of building my network. Also I have to be careful around other people who have trauma, most of them haven't learned to manage it, and that's dangerous for someone like me. Like a recovering alcoholic can't be in a relationship with a raging alcoholic, one just brings the other down.

So for me, right now, it's really about learning to say no sooner and take my ball and go home instead of hanging with people that aren't making my life better or helping me build the kind of quality network I think I need.

Really interested in your feedback on this. I'm willing to entertain the idea that I've got reciprocity all wrong. But I can't go back to zero reciprocity. It's too hard/wearisome saying no to people all the time (especially when I came from little and now have so much, just makes me feel guilty). Easier if I just kick 'em out.