Props to everyone who has made this choice! I can empathize with how difficult the transition can be, even when you have multiple supportive parties telling you that you look great (or will look great). As a early 30s male, I recently made a similar decision when I stopped using an expensive hair product that hid my relatively advanced male pattern baldness. After almost 10 years (I started balding early), I FINALLY bit the bullet and just buzzed my hair super short and I'm so happy that I did. Not only am I saving something like $50-75/month by not buying that product (not to mention being able to cut my own hair), but I even prefer my new look, despite being so afraid to go for it.
Plus I am much happier being able to just be me, not living in terror of bumping my head and creating a bizarre bald spot, never being able to go swimming, etc. And I swear I get more appreciative looks from the ladies than I used to, perhaps just because I carry myself more confidently. My wife certainly loves it, which, of course, is the far more important thing! :)