Years ago, during one of my earliest periods of going sly, I had 2 different buddies who were losing their hair. One said he'd been considering shaving what was left and asked me a lot of questions about method, feel, maintenance, etc. I answered his questions, told him how awesome it felt being sly and a week later, he showed up shaved clean and said I'd helped him make the choice. The other balding buddy didn't say anything until one day that he and his wife came to a party at my house and my buddy had shaved his head. His wife then told me that she'd been pushing him to do it for awhile, but it wasn't until he saw my shaved head and how good it looked that he finally gave in. So she was grateful to me for leading by example.
I think that really is the best way ... living proudly as whomever you are instills confidence is those who "wannabe" and causes confusion in those who harbor stereotypes.
I've got a co-worker on the fence about it. I think he was impressed by my decision to go sly despite my earlier contention of preferring a full head of grey hair over no hair at all. (That belief is no longer true, btw.) He says his son is sly so, since they look alike, he knows how he'd look himself.