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Tax is unavoidable, but the difference in rates is big enough to be worth some risk, I think. A 10% drop in price is no worse than paying short term instead of long term rates.


but the difference in rates is big enough to be worth some risk

It is, and I won't even try and argue against that. However, short term capital gains are taxed at the same rate as my ordinary income. In the worst case, when I make money my tax situation is no worse than if I made the money working. That's good enough for me to just not spend the CPU cycles. Yeah, yeah, in some situations I'm leaving money on the table. I don't care because I'd rather spend the limited cycles I have for investing in finding the next good pick, not tax avoidance. At the very best, I can save 28% on taxes. Spending my time finding good companies, however, can do much better than that (see: TSLA, AAPL in the 2000s, et. al.). I'm also lazy, and find tax stuff boring in comparison to evaluating whether now is a good time to get into Lending Club.

Another way to look at it is with an eye toward always preserving capital. IOW, if I'm getting taxed I'm making money (and therefore not losing it). However, I could screw around with some tax avoidance scheme and end up losing money. I'd rather break even or slightly below than lose money; live to trade another day. So most of the time I set an 8% trailing stop and call it a day, let the machines worry about it.

This isn't investment advice, and even if it were there are a lot of unspoken assumptions that I haven't outlined. It's probably not even the smartest way to maximize gains. But for me, personally, it's the right combination of not overthinking it, not spending time obsessing over my portfolio, and still making positive returns. And last time I looked it up, I've had two negative years in the last sixteen. So it works for me (though at my age I need to start looking less at the TSLA's and more at those sexy, sexy bonds).




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