I think there's a good chance that you just hate work. Not that you're lazy, not that you hate working or doing work, because that's different. Corporate "work"

I think there's a good chance that you just hate work. Not that you're lazy, not that you hate working or doing work, because that's different. Corporate "work", the institutional nonsense that people have to do to prevent higher-status people from turning off their income, is an awful waste of time and involves very little actual work. It deserves to be hated. I understand the unhappiness of being an IC, especially in midlife. You're not respected in that position; software is manage-or-be-managed, and if you're still in a "be managed" position at maturity, it's not a good look. Still, I think you'd also hate being a middle manager, to be honest. I know I did. You're not actually "mentoring" people as a middle manager (or as a PM; PMs exist to give executives a second management structure so "product" and traditional managers can be pitted against each other). Instead, you're a performance cop who works for even bigger assholes than you did as an IC. You'll have to be the face of awful decisions that hurt people's careers, and you'll have to make some really shitty ideas look like they were yours, so the execs (who asked you to push said shitty ideas) can distance themselves and be loved. You're in the position of transmitting orders, and you can't really protect your people. I also don't think you can assume that you would have made Director just because a less-talented colleague did. Capitalist Party politics is its own game, and the people who are good at it are usually good at literally nothing else. I don't think you should feel stupid for making a career mistake, though. The game is rigged and the Capitalist Party is hopelessly corrupt. If you weren't born into a hereditary upper class, you probably were never presented with any good options--just bad ones that looked good at the time. Your Director-level colleague might be working 70 hours per week and losing his marriage. He might die at his desk of a heart attack at 47. Anything can happen in the corporate world for all bad values of "anything". As for what you should do, I'm in no position to give advice. I don't know you or your circumstances. You certainly aren't alone, though. Corporate capitalism has to pay people with constant expansion--not only do they expect their incomes to go up, but they expect the rate of increase to go up--to get them to overlook its awfulness, and the system can no longer support this. I won't tell you that it's going to get better (it's going to get worse first) but you're not a loser for making bad choices when you probably didn't have any good ones. You shouldn't feel bad about yourself. You're surviving. That's all most people can do right now. Some people, usually through no fault of their own, can't even do that.