I've known any number of people in Massachusetts who have made the entirely rational decision to just hit the beach for a year rather than trying to deal with the potential consequences of a non-compete. And as someone who worked for a small company in an other state, we basically wouldn't even try to deal with a potential hire who might be covered by a non-compete--enforceable or not.

I can't speak for Massachussetts, but in Washington state non-competes have to be narrowly tailored resulting in them being relatively hard to enforce.