I understand how you feel about embarrasement.

But nearly everyone uses something as a crutch to make them feel better. Take women and make up, I've dated some women in the past that would never let me see them without makeup and feel really self conscious about it.

A big part of wearing a wig/hairpiece is faking it, no matter how you feel. Its projecting a f*ck it attitude. Take pride that you are doing something to make YOU feel better, if you look at yourself in the mirror and like seeing yourself bald then be bald. But if you are willing to spend the extra 2 hours a week on maintence to look 100% better, thats being proactive and not being lazy.