Here's the story of how I made the decision to cut my hair short and just let go of the combed back hair on top.
I had been losing my hair over the years starting when I was 20. I had settled into the comb back style a la Jack Nickelson. You've got to do something with that hair on top as it thins, so slick back it was.
When my D was little we were at the swimming pool one day. As I was watching D swimming around in the pool, I noticed one of the other dads swimming around in there too. He had the dreaded comb over style of attempting to hide his baldness. The reason I noticed him is because every time he he would come out of the water he would have this awful lock of hair hanging down to his shoulder. That wasn't even the worst of it. To reposition his comb-over he would give his head a quick snap and like a whip his hair would slap back on the top of his head (shlaap!). I was really funny to watch.
That was the day I went home and cut my hair short. I didn't want to be a spectacle at the swimming pool or in high wind. That was about 12 years ago and it looks a feels much better this way. My wife likes it better this way too.