Probably not that big a deal to any of you, but it sure was to me. When I was 22, I got my long hair cut towards the end of first year in University only to realize that I was losing my hair. It had progressed quite a lot, but my long hair had been masking it. With the shorter hair there was no hiding it so I wore a had for the final few months literally at all times, although it was pretty obvious to everyone why.
Over the summer break I drove myself crazy worrying about it, until I stumbled upon a video of Patrick Stewart describing his struggle with early hair loss (he went as bald as he is now by 19) and it inspired me to face it head on.
I spent that summer hitting the gym and cycling, got in good shape, shaved my head and went back to University. But on the morning of the first day, I put my old hat in my bag just in case.
My moment of facing my fear was when I threw it off a bridge on the way, so there was no chickening out, and walked my freshly shaved head right in the front door looking an absolute threat.
That video really reached me, and if I ever meet Patrick Stewart it'll be the first thing I tell him :)