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When does it make sense to sell and reinvest?

T
Apr 24, 2026 · 18:01

Let's say I own a stock with some gains. Is there a mathematical formula to determine if it would be more profitable to sell now, pay LTCG and reinvest at some later date with a slightly lower entry price vs. just holding and paying LTCG in 10 years? Or in other words, is there a specific drawdown % required to offset the immediate taxes and loss of associated compounding in the long run?

I understand taxes shouldn't drive investment strategy, timing the market is bad, etc. I'm just curious from a mathematical standpoint.