I put it off as long as possible. By the time I decided it absolutely needed done, I was having to do his hair at least 3 times a day (after each time he slept) in order to have it look kept. Every time we left the house I had to redo it and then just sitting in his carseat messed it all up again. It was becoming a battle.
The problem wasn't really the length. The issue is that he had SO much hair at birth, that when his older baby hair started growing in, he had two definite textures of hair going on at the same time. The top half of each hair was only slightly curly and fought staying curled, while the bottom half was growing in much thicker, courser, and curlier.
So I did it. I thought about taking him to a barber, but decided to try my hand at it first. It really was much easier than I thought it would be. He was less than thrilled with the idea of having to sit still for any length of time, and I ended up having to finish the cut with him standing facing backward on the chair. Next time I will enlist Scott's help with holding him still. Sharp scissors near a wiggly baby makes me nervous.
Here's his before (without me attempting to make it look nice).
And here's the after. I cut about 2-3 inches off! He looks so much more grown up now (and yes, I fixed that random stray piece on the right after I took the picture). You can tell how pleased he was with this whole process.
In the end I'm really glad I finally just did it. Taking care of it is back to being really, really easy. A quick spritz and a little moisturizer every day or two is all it takes to stay looking nice.