I agree. Contracting is great, and no one cares about your age, just what you can do. I've been paid and paid thousands of dollars without ever actually meeting someone in-person.

He should absolutely check his employment agreement, though, and make sure he doesn't:

* use company equipment

* do any work for a competitor

* work on company time

Contracting also is helpful because it is something he can dip his toe into without a large time commitment (as opposed to a job). I'd suggest he reach out to people he has worked with in the past that have left the company (LinkedIn is good, but Facebook might work well too). My go-to phrasing is:

"Hiya, hope you are doing well. <Anecdote, like 'remember when we shipped project X? Guess what, it's still running today'.>

I'm reaching out because I'm looking to do more contracting and to expand my network. In particular, I want to do <the type of work he wants to do>. I'd prefer to do it off hours, about <X hours a week>.

Do you know anyone who is looking for a hand? If you do, or think of anyone, I'd sure appreciate an intro."

This phrasing is far less direct than "Do you need help" but conveys the same message.

He should also think about a rate that he'd work for, as that will likely be one of the first questions any possible client will have.