headache when putting hair up

I've had this problem for awhile now. I always get a headache when I put my hair up, whether it's only half-up or actually in a ponytail (I'm not too good at updos, so those don't stay up for long). I'm wondering if anyone had this problem before. My hair is around shoulder length. Maybe I should put it up for short times to let the roots strengthen? What's happening?

I second that. Try making it a little looser.

And it's been over a decade since I had short hair that wasn't long enough to put in a ponytail, but it seems to me that when it was growing out, I had the same problem. Maybe your roots do take some getting used to it.