Got my mind on my money and my money on my mind...

There's a fine line between being a nice guy and a doormat. I think I'm squarely in doormat territory.

This, of course, the continuation of my saga of non-profit loansharking.

So I was supposed to get my money by Monday. I hadn't heard anything by Thursday, and happened to mention to a coworker who is also a good friend what happened. He instantly offered to call the contracting company that the guy worked for, but I asked him not to. Evidently, he did anyway, because the next day another coworker told me that he had talked to the contracting company and would make sure I got my money back.

So the next day I get a call from the contractor - he can either give me the money over the weekend or Monday during work. I tell him Monday is fine.

Monday I don't hear from him until late afternoon. He says he won't be in my area until after 6. I agree to meet him at the parking lot of my gym at 6:15. So I only do an hour workout instead of my usual 90 minutes, and go outside to meet him. Not there. Check my cell, and he left me a voicemail that he was running late.

He shows up around 7:15. He only has $190. He'll give me the other $87 he owes me next week when he gets paid again. And as he's leaving he tells me "if you have any problems, call me. You have my number, and I don't appreciate getting calls from other people. I apologize, and tell him I had asked my coworker not to call.

And then I got in my truck and drove off... and started wondering why I apologized. Yes, I should have manned up, tracked down his number, and called him myself. And I do feel bad that it probably hasn't helped his career that his contracting company knows he's a deadbeat. But at the same time, I don't appreciate someone borrowing a fairly significant amount of money from me and not paying it back when he said he would. He could have just as well tracked down my number and called me, and, I feel, probably should have.

And I'm annoyed that I'm probably going to have to go through this whole sit in the parking lot routine again next week to get the rest of my money.

I'm starting to think that this whole thing is because of my complete lack of confidence in myself, my general hatred of myself. I loaned him the money in the first place, knowing it was risky, because I didn't have the balls to say no, because even though I would have had very legitimate reasons not to risk my money, I couldn't bring myself to say no. I didn't call because I "don't like conflict", which is another way of saying that I don't have enough confidence to tell people things they don't want to hear, even when I'm completely right. I found myself willing to just let it go, even though that violates every conservative/libertarian property rights principle I believe in, and even though I'm generally hyperfrugal with my money, not spending what I don't have to and looking for every opportunity to make more.

This isn't much different than the reasons I'm single, that I have a very small circle of friends, and what is probably a dead-end job - I don't have a whole lot of confidence in myself, and I can't convince a woman, another person, or bosses that I'm worth anything. It's sort of a spiral of failure - the less confidence I have, the more introverted I get, which gets me nowhere, which makes me feel like even more of a failure. But I don't know how to get that confidence back. I feel what would help is if something good happened to me - relationship, promotion - that convinced me that I was not completely worthless. But those things are unlikely to happen as long as I figure that I'm completely worthless.