There is noting wrong with the look, it is just another hairstyle choice. Sure, some will question why. But just say it is what you wanted. One guy I work with told the co-workers that he was giving himself a buzz and forgot there was no guard on the clippers until it was too late. But he kept is shaved afterwards, so no accident. As to work, it is a common hairstyle and will not be a problem. Believe me, as a guy that did some hiring in my previous job, I was much more comfortable with employees with shaved head that some of the more edgy hairstyle out there.
Family will be family, just prepare for the questions and disapproval.
BTW, when I first shave, I also had a full head of hair. Nature has since caught up for me. I had some of the same concerns when I shaved. Once I did, and kept at it, I was glad I did. The questions from work and friends only lasted a few days. Family depends on how often you see them. If you keep it shaved, they will stop.