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One person wins. The other loses. That's the way it's always been. Capitalism at it's finest.
Who is the "One Person"?
Not sure what you mean by "Zero Sum" . . . Maybe SunTzuSays can shed some light on that one.
However, since most of my retirement is wrapped up in Roth IRA's and some 401K's, I know that the Ira's are somewhat safe, but the 401K's can get blanked out if their portfolio managers screw them up to the point where they lose value to zero then they are gone for good. After 9/11 I moved a lot of my high risk investments to annuities where they are guaranteed to not fall below the original purchase value – that was the safest move to make at that time, I thought . . . Only time will tell.
Zero Sum Games are usually behaviors that involve transactions where nobody benefits without someone else's loss.
That's not how the stock market works. Nor is it how capitalism works at its finest Jared (as usual, you clearly have no idea what a market is).
As far as your investment portfolio… IRAs are not inherently safer than 401ks. Both are merely tax vehicles for saving and it would depend on what you have in either to see how they might be wiped out by poor investment choices or inflation or some other hazard. If the Roth accounts are in "safer" investments, that's another thing entirely. But I've found lots of people seem to believe that simply by virtue of the name change, they're in a safer place. They're not.
Annuities I tend to avoid selling people but with the bond market being as it is because of the reserve rates, it's hard to say that they're a bad buy when you're approaching or in retirement. I find it smarter to get people into other things though which will continue to grow (annuity keeps growing until you tap into it). Suffices to say, I'm not a fan of guaranteed value on annuities because insurance does the same thing cheaper.
I'm also not sure why 9-11 was an important marker there. Perhaps it makes sense to move retirement assets out of high risk investments as one approaches retirement or is in retirement, but I don't see why you'd want to move them just because the stock market goes down (perhaps the stock manager isn't a good one, that'd be a good reason to move them at that time). Volatility of the market is much higher when it drops, meaning there are lots of opportunities for gains. I call large stock drops "sales".