Nothing is better than getting paid to do something that you would do anyway. There aren’t many professions that you can say that about, but I think that’s still true of IT. IT lives in a junction of logical thought and creative expression that stretches and challenges your mind like few other things can.
Yes, IT is under attack from outsourcing, foreign competition and a poor economy. But what isn’t? And while outsourcing support looks good on the bottom line, it’s often more of a cost shift than a savings - fine when shifting costs to your customers but not so good when shifting costs to your business units.
So I think that it would be a mistake for Tim Bray to guide his son away from this profession. He should make sure that he has exposure to other careers. But if the kid has the knack (he certainly has the genes), then I wouldn’t fight it.