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Old 12-12-2009, 04:03 PM   #21
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Join Date: Dec 2005
Posts: 1,225
I'm FIRE'd and in a low tax bracket, so this year I did enough sales to eat up all the zero cap gains tax bracket, figuring that will go away soon so I might as well feast while I can.

But I draw the line at intentionally incurring cap gains tax as a speculative move anticipating higher CG tax rates. I figure it's best to defer paying my CG taxes as long as possible. Who knows, maybe in a decade or two things will swing the other way again and CG tax rates will be lower than they are now, and I will also have deferred paying them for a decade or two. Or maybe capital markets will collapse and I'll end up with losses rather than gains decades from now.

I always have flashbacks to the dotcom era when people I knew incurred huge tax bills by exercising their qualified stock options early intending to save a few bucks on tax, and then were caught when their values plumetted and not worth enough to pay their tax bill. I know one guy whose net worth peaked at 2 million, then dropped to $10k after paying his taxes on prematurely exercised options. And I know others who were left with big IRS bills and no way to pay them. It's not really a rational fear because we're talking about doing much less bold moves here, but it's a fear I respect.

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