I used "picky" in another reply and I apologize since this is obviously a sensitive subject and you're right that it's not the most generous word choice.
That said, I think you do need to find a balance. Using your CTO example: if you only interview a single person, you're certainly not selective enough. But if you spend over a year and interview 100+ qualified candidates and still haven't found a mutual fit, then yeah maybe you're being too selective, or just not realistic about how you stack up against the competition.
There's a saying in hiring that you might have heard that says "hire for strength, not lack of weakness". That might apply well in your case too as a way to kind of mentally smooth over accepting someone that maybe doesn't meet all your standards. Like maybe they're well below your physical attractiveness standards or not well spoken, but they're incredibly kind or funny or interesting to talk to.
If you're pursuing a guy that you would have also been interested in when you were 28 and in your physical prime, well, that probably means you've got a lot of competition that will be tough to overcome. Perhaps a weird way to think about it, but it's better if there's something faintly eww about him from your 28 year old self's perspective, that you're now willing to look past.
Anyway, I really wish you luck. You seem like a great person and it's a shame that simply by the mistake of waiting a bit too long in the biological game, you're in a tough spot. While men have their own set of challenges, we don't have to deal with a deadline on figuring these things out.
You don't have to apologize for the word picky, I can easily say words like that with friends without them being triggered, similarly to the word ,,taken'' in another thread.
It's an expression that has been used for a long time, and I don't even see that much difference between the word picky and selective (maybe because I'm not native English speaker, but in my language they are translated the same).
It's really hard and vulnerable to put yourself out there like this. I think it's good to be as kind and generous as possible in these kinds of conversations even (or especially) if there's some brutal honesty involved.
That said, I think you do need to find a balance. Using your CTO example: if you only interview a single person, you're certainly not selective enough. But if you spend over a year and interview 100+ qualified candidates and still haven't found a mutual fit, then yeah maybe you're being too selective, or just not realistic about how you stack up against the competition.
There's a saying in hiring that you might have heard that says "hire for strength, not lack of weakness". That might apply well in your case too as a way to kind of mentally smooth over accepting someone that maybe doesn't meet all your standards. Like maybe they're well below your physical attractiveness standards or not well spoken, but they're incredibly kind or funny or interesting to talk to.
If you're pursuing a guy that you would have also been interested in when you were 28 and in your physical prime, well, that probably means you've got a lot of competition that will be tough to overcome. Perhaps a weird way to think about it, but it's better if there's something faintly eww about him from your 28 year old self's perspective, that you're now willing to look past.
Anyway, I really wish you luck. You seem like a great person and it's a shame that simply by the mistake of waiting a bit too long in the biological game, you're in a tough spot. While men have their own set of challenges, we don't have to deal with a deadline on figuring these things out.