My hair is my nemesis in some ways.
I have fine, curly hair. Despite hating being a girl as a kid, I never felt like cutting it. So I don't think scissors touched my hair until I was in my 20s, when I realized I should at least trim the split ends. Needless to say, my hair did not always look awesome in those days. It is fine enough that it forms giant tangles if I don't care for it. In retrospect I wish I'd gotten in the habit of cutting it as a small child, but after a while it just felt like cutting my hair would change who I was irrevocably, or something.
But, by high school I'd figured out things like conditioner, avoiding brushing it (vs combing it with conditioner), etc, and it was not a disaster, though I could have been a lot more stylish with a bit of attention to it.
In my 20s I got my first professional haircut, which looked awesome. Though I only got it cut twice. In my 30s I found a hair stylist who was great with curls, and she's also the one who did the undercut. I was really attached to having long hair, but I wanted something edgy, and this was the perfect solution. I wish I'd done it years earlier. That stylist moved to Portland (common story - SF is too expensive for anyone but tech folks these days) and my new one isn't quite as good, so I'm still on the lookout.
I alternate between wearing it down and up in a messy bun. I can tell I need a haircut because just in the past few weeks it's been hard to get the bun right -- too much hair. I cut it every 6 months or so. I can almost imagine cutting it short now, but I don't see any particular need to. Though, they just discontinued my magic detangling conditioner, so I might cut it out of frustration!