So this is something I get asked on a regular basis! I find it quite amusing if I'm honest, because I always get asked it in relation to things I do nearly daily. A few examples: people see my website and say "you should be proud of yourself...are you?"; I secure a meeting with a politician and people say "I could never do that, are you proud of yourself?"; I give a talk and people say "you're so brave, are you proud of yourself?".
The honest truth is...not really. I have moments where I look at the website and I think "wow, I built this from the ground up, that's pretty damn cool!", but that's about the extent of it.
I guess the only way I can really explain it is that I look at the things I'm going and think "that's good, now, what next?". I don't generally stop to take pride in anything. I feel like I haven't got the time - I only have one lifetime, and that's not very long when you're trying to change the world!
When I tell people that no, I don't feel pride, they seem horrified, even worried. Here's the thing; there's no need to worry about me just because I don't feel proud of the work I'm doing. I feel content! Occasionally frustrated, because sometimes people do make you feel as though you're talking to a brick wall, but most of the time I'm completely content.
About once a month I hit burnout, but because I'm generally pretty good at getting ahead of myself with posts, that's okay! I can take a week off, go out and do stuff like climb mountains or play Cards Against Humanity with a group of strangers.
So it's okay that I don't necessarily feel proud of what I'm achieving. I'm okay. Everything is okay!