I got into the corporate world right at the ripe old age of 21 (seriously, I was too stupid to have gotten through college and b school, I had NO idea about the real world besides were to buy suits), a few months before 9/11 and then Enron and Arthur Andersen. The company I worked for was court appointed to run Enron, so that was one of my first assignments and we dealt with a ton of the AA restructuring too. It was a cool gig in general, but for a girl from Nashville, who have traveled a decent amount, but not like I was throw into, it was a GREAT learning curve, and terrifying. I remember Smith Barney and I lost Bear and Lehman when they went out. It was a huge part of my book of business (of course) and all the rest of it wasn't doing great either. I remember crying in my boss' office about making up the millions of shortfall in our base when the market was like that and him pretty much telling me it was the end of the world and there wasn't enough business left to make it up. That was scary. I had just gotten my first divorce too. I was at WDW with my folks actually when my dad told me the dow was 6000. It was traumatic. I was in NYC when Lehman's people where streaming out of the building - that was insane.
The point is, 2 years later, business was, and continues to boom, and it can be the same in tech, defense, retail, whatever. The OP's son will find his way, but no matter what you do, there will be crazy bumps.