From one who's been there, if you've got a combover you know you're losing your hair. From that point, if you've inquired about the sly option you're really ready to ditch the flap anyway. But what slows you down are the worries, and inertia--that's a male thing. Men don't change hair styles often--some never. We also don't change barbers or wallets for that matter. This is just hard wired into us. So, in addition to the worries about head shape and reaction of our family and friends, the inertia has to be overcome. Those of us who have gotten to sly somehow overcame it--in my case for some reason when I sat in the chair--already knowing that at some point I had to get real--I just told Louis "Buzz it." From there it was a short eleven day trip to sly. Others it might take longer. In one action I undid two established facts of my life, hair style and barber. Barber since I could buzz myself then and that I only realized after another trip to Louis to take it to a 2 from a 3. I did the 1 myself, and w/ the urging of my cousin who was already sly, I did the deed four days later.
How we get to the guy to make such a basic move is an issue, and it's hard because of our ingrained habits.
By the way, I still have the same wallet--it's at least 10 years old and I have no desire to change it at all and no one could persuade me to do so.