"It's only hair, right? It will grow back." That's the one thing to remember when deciding on if/when/how to spruce up your look via your hair.
I had such a conversation with myself a few weeks ago while in Denver. My friend and I were minding our Ps and Qs taking her dog for a walk when we ran into her hairstylist. He'd just given her a new fierce look and we started chatting. I wouldn't say I'd been previously married to my 'fro, but I was pretty comfortable with it. However, I was open for a change. What to next do with my hair had been on my mind for awhile and before I knew it me and her stylist, Stevie of Studio Stylists, started talking about different styles for my hair. He showed me a picture of Pink and suggested something along those lines. As I was open for a change and was on my own Rocky Mountain High (due to the warm temps, folks, not the other high...), I was an easy sell. Soon enough I was in his chair undergoing a Tall T transformation.
It's amazing what a new 'do can do! I have gotten more compliments than I can remember, the most notable being from a 50s REI-clad woman on the subway. (That one just really touched me for some reason.)
Sometimes you just have to jump in and do something you otherwise wouldn't do. I'm not advocating for you to shave your head after a five minute deliberation, but it is important to shake things up on occasion to remind yourself that you're alive and to LIVE! It keeps things interesting. That's what we are here for: to be in the moment and live.