Having bounced around from job to job during my adult life, I've spent a fair amount of time thinking about 401(k)s and other retirement tools and bemoaning their weaknesses. The big problems seem to be that they don't really work for the self-employed, vesting schedules make employer matches meaningless (they're supposed to promote staying at your job but there's no such incentive for a company not to fire you), and actually getting real money out of your plan is a crapshoot that the market is high when you retire.
This Time article is a bit inflammatory, but raises these points and more:
But retire rich? Don't bet on it. The average 401(k) has a balance of $45,519. That's not retirement. That's two years of college. Even worse, 46% of all 401(k) accounts have less than $10,000. Today, just 21% of all U.S. workers are covered by traditional pensions, and the number shrinks every year
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It'll be interesting to see where mine ends up in 30 years, but I don't have a lot of confidence that I'll be living the high life...
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