You need a break from your social environment, maybe doing it before a long vacation, after changing a job or moving to another city. One day bald next day full head of hair is not good.
Sorry, Mike, I need to disagree with you on this.
Taking a vacation is not a bad idea, grow a beard or mustache if you don't have one, or come back with it trimmed differently, if you do. Some guys even shave (I despise that word), but if you do, you can always start growing it back.
I went from completely shaved to having an NW6 fringe for six months to a full-on 14" Viking Top Knot, with faded sides. I also cut off about half the length of my beard, that was the first thinks people mentioned.
The people I was closest to, I told. The other, nothing. All of the reactions I got, were positive. Now it's a year, many don't even remember me bald.
Old friends who I have not seen in a while, say, wow, you grew out your hair, looks awesome.
Recently I got a new system, with curls. I also opted for a longer style, tousled, and less military. Only one person even saw that I had a new haircut... did not even question how it was now, much longer, overnight.
I am super confident about my hair and don't really give any F***S about what others think, so that also, adds to it.
The idea is that you are doing this for you, and for no one else. If you feel like you are hiding something, you always will, no matter how great it looks.
Steve