Is he shy or introverted? Both? I’m actually both. When I was younger (very young) I started out as being extremely shy. The older I got, however, I also became more introverted just because it’s my dominant personality trait. Very hard to deal with growing up because I never felt normal. Still don’t, but I love myself now because I am different.
Working definitely helps with the shyness factor, though. I hated it when I started my first job, because I was so shy I couldn’t talk to anyone. And I felt like an idiot whenever I did cash transactions with customers. I had a fear that I was too slow, would give them the wrong change, or simply forget something. But, the more I did it, the easier it got. It forces you to be a little less socially awkward, because you kinda don’t want to get fired. It’d be humiliating. And humiliation is exactly what shy people try to avoid.
I do suggest letting him pick where he works though, as long as it’s a job that requires him to deal with people in one way or another. I say let him choose because if he is introverted or generally anti-social, it could be for a number of reasons. And it’s not necessarily a bad thing. Trying to force an introverted person to be extroverted is actually flat-out wrong. No one would ever ask someone extroverted to turn into an introvert – and that’s good. People are different and that’s all there is to it.
Besides, if he is introverted, working will give him the chance to get to know people he actually feels are worthwhile, other than having to conform and be like everyone else, and just being friends with the first person that comes along.