I will be bald starting a week from Friday. I have decided to go for it. Comments from newyawka and Rob were especially helpful and all you guys have been a great help.
So I'm saying goodbye to the 'corporate' haircut in my photo when I say goodbye to my corporate job next week. I'll start my new blue collar job as a bald man.
............
Congrats on the new job and your new start on life. You're in the right position now, especially to shave it smooth. Think of it as a whole new beginning. I can really relate to you Tim because I went through the same type of thing as you're going through, three years ago just this past month. A total life change.
I can only encourage you to go with it, remember you're making a fresh path in your life, practically starting over. What better way to do it than go out there and try something you know you want to do?
I think you're going to be fine. Hang in there and face it proudly, feel the confidence that will come over you when you do the things you want to do. Put it out there.
........Good luck! 
So, I've decided to go through with it. I have an appointment with the clippers next Friday after my last day at my current job.

I told my barber I would rather start with a buzz and he said "Forget it. Just get it all shaved off at once. If you're going to do it, then do it right! "
For twelve years this man has been cutting my hair and asking me if he 'took too much off'. Now he is looking forward to shaving it all off! My hair is very thick on top and in the back but he said it would only take a few minutes and I'm done.
He said he would leave a great shine on my scalp.

That will be a new one for me.
The barber is going to take before-and-after photos. We talked about my new blue collar life that I'll be starting - as you say, a whole new start in most ways.
It will be more than a head shave - it will be part of a transformation that I hope will be a good transition into something new. The old image has to go - all of it.
So I'm going to bring my coveralls and work boots with me to change into before the head shave so I can 'shed' (good word

) and be free of the useless, expensive, fancy symbols that I have used to create the executive persona that used to mean so much to me : the Armani pinstriped suit, the necktie, the starched shirt, the Italian captoe shoes, the black Brooks Brothers socks, the cufflinks and the briefcase
along with my corporate haircut that goes with them. It's all part of the same fake package. For some it is exactly right. But it no longer fits me.
I guess I will really look like a new man when I leave the shop. But WHAT I will look like - well, I will soon know!
How will people respond differently? I don't know. I wil have to see. They are used to one "Timothy". Now there will be a new one.
I will be shorn of my image along with my hair. I have shown that to the world for years. I don't know what the new image will be. But that's for the future.