Another update: I just learned what the meeting is for. He wants me to talk with my friend and his boss about my background and their needs. If there is a fit, he'll schedule a technical interview with other people.

I feel like this is a step backwards. Wasn't that what our first conversation was for? Each step forward I take with this, I just become more convinced that it is never going to work and that I should have just said no immediately. I'm looking forward to seeing my friend tomorrow to discuss this.

Also, technical interview, really? I'm already doing technical contract work for you guys!

Re: extended time off: I'm not sure how to really explain it, but, yeah, I just find other stuff to stress about. Interpersonal stuff is a big focus, just like it was when I was at the office. I have fewer work problems to solve and I think I spend that energy fixating on kind of minor stuff. Maybe it will be different when I finally get back to work on something that might lead to self-employment income.

When I mentioned this to my bf a few months ago, that I felt just as unhappy now as I was when I worked, he looked at me with wide eyes and said that I seemed much better. I think if I went back to work, I would quickly remember just how horrible it is to have no time to do anything.

I've also found that tasks just sort of expand to fit the time I have. The busy/have to get this done/not enough time feeling hasn't really gone away. It's been incredibly enlightening to see that these problems I've had at workplaces really come down to the way I cope or don't cope with things. I have more bandwidth to realize this now, I suppose.

I'm really trying to deal with this situation the way a responsible professional would, but I have no idea what that looks like. Which is more responsible - to recognize that this situation is not going to work out or to cultivate a more neutral attitude so this sort of stuff doesn't phase me?

Having a boatload of vacation time and the seniority to use it is great! I'd caution you against selling yourself short by assuming that you can't get another gig like that elsewhere - not that you should leave your company just because your current boss is ineffective. I think we really sell ourselves short when we think that we can't do better. It's such a limiting way to think of our options. I feel like I kind of learned this the hard way, as I always thought that I was doing well, but in hindsight, I was selling myself short.

But it sounds like you are at a good company, just not with a good boss right now. He can't go on doing what he is doing forever... and I'm still keeping my fingers crossed that you hear back from that other woman