Playing the market is indeed a chump's game,
if we're talking about trying to make big money by constant trading.
But to be fair, as a long-term investment it's held up pretty well. I'd have no problem with younger people putting money into stocks, particularly using dollar cost averaging.
If you have lots of money, investing in real estate (cash-generating investments, not "flipping") is good.
Being debt-free is a lot easier if you're in a steadier business, and not putting two kids through college. :)