Great question Tyler, I can tell you from my own experience:
1) The faster you take that step to sly the better off you'll be. So many of us agonized for weeks, months, years over our hair loss and the moment we finished shaving it all off we all go -- dang I wish I had done that years ago.
2) Yes you look different. You may experience shock for the first two weeks after shaving your head -- but that will quickly turn to awe. When I walked past the mirror I was in total shock over the change in my look (I wore a hairpiece so I went from a full head of fur to sly).
3) Don't ask people if they like your new look - TELL them how awesome it feels and how much you love it. People's opinions are shaped by how you react.
4) Walk tall, don't slump, don't cower, think Bruce Willis kicking rear in one of his movies. You now have the power -- you are in control. Act like you're in control
5) Look people straight in the eyes - show that you're confident in your new look. Don't act like you're ashamed.
6) Help a brother out. You'll surely see other guys with horseshoes that are eyeing your skullet. Smile and hand them your SBG business card.
7) Look around - you're not alone. On Thursday I was standing in line for lunch and looked around. Of the 10 guys who were in the cafe - four of us were sly.
Its just freakin hair. Hair doesn't define who you are - although fear, agony, depression, and hiding behind your hairloss does! The quicker you take that step the quicker you're going to feel freedom and happiness.
9) Listen to the guys on the forum. We all say the same thing -- its a huge positive change.
10) Pick up a pair of clippers at WalMart, Walgreens, CVS, or elsewhere. Its simple to buzz your hair down with no guard. It takes about 3 minutes to do the job and you're there. Sure you can start with a #3, #2, #1 guard to transition to sly -- but until you take the step to #0 and a blade you won't understand the freedom. So skip the numbers in between and go for the blade.
11) Share your success stories with the guys on the board. The more positive stories the better. Looking back over the past 6 months -- there's only been a couple of "oh no why did I do it" stories and interestingly enough -- those stories tend to be due to someone making a negative comment. See Item 3 above to avert those issues.
12) Ask for help and encouragement. The guys who actively participate here are awesome. If it wasn't for SBG I'd still be shelling out hundreds of dollars a month on a piece of fur - still feeling terrible about myself - agonizing over my "hair". After nearly 4 months of "no hair" I can honestly say that I haven't been happier about my looks since high school. Having a shaved head isn't even something that I think about -- it feels natural, looks natural, and other than women walking up and telling me how hot they think guys with shaved heads look and wanting to rub it - its just normal!
Now -- man up -- grab a blade -- take care of business -- get on with your life.