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Yep. Another way to look at it is this: I don't invest in way that maximizes my expected portfolio size when I retire; I invest in a way that minimizes my chances of falling short of what I need. These are two very different goals.

Indeed! The scenario that prompted my OP was to spend 10s of thousands of dollars now to convert an IRA to a Roth in order to save in taxes later, though I still think more would be lost to taxes.

Once you've paid the taxes for a conversion, the money is now out of your hands. If the investment goes down in value, you've not only lost the value, but also the taxes you paid.

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