The Tax Rules for Your Personal Investments article in AAII's 2025-2026 Tax Guide, highlights something many of us don't realize until we've been investing for a while: timing can be just as important as the investments themselves.
Between ex-dividend dates, holding-period requirements for long-term capital gains, year-end mutual fund distributions, and the ever-tricky wash-sale window, tax rules often influence when we buy, sell, or harvest losses.
But timing cuts both ways. On one hand, delaying a sale by a few days or avoiding a late-December fund purchase can save real money at tax time. On the other hand, letting taxes drive every decision can conflict with your long-term strategy, risk management, or portfolio rebalance schedule.
So, I'm curious:
How do you personally balance tax timing with sticking to your actual investment plan?
Do you:
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Delay sales to qualify for long-term gains?
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Actively track ex-dividend dates or holding-period requirements?
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Avoid buying mutual funds right before distributions?
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Tax-loss harvest but worry about the wash-sale rules?
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Or do you ignore most timing details and let strategy lead the way?
There's no right approach, just different philosophies. Would love to hear how you think about it. Read the full article here.
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Jenna Brashear
AAII Community Manager
Chicago, IL
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