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Rebalancing: Why Selling Winners and Buying Losers Sometimes Makes Sense

Beginner Investing • 5 min

Rebalancing forces a systematic 'sell high, buy low' discipline that deliberately fights your own instincts. Left alone, a portfolio's actual mix drifts over time — if stocks have a great year, they'll naturally grow to be a larger share of the portfolio than originally intended. Rebalancing means periodically trimming what's grown and adding to what's lagged, to return to the original target allocation.

It often feels emotionally uncomfortable — selling a winner and buying a laggard runs against most people's instinct to 'let winners ride.'

Insider Angle: that emotional discomfort is precisely the point. Mechanically buying more of what just underperformed and trimming what just outperformed is a disciplined way of buying low and selling high, without needing to correctly predict anything about the future.
Try This: Imagine a portfolio that started at 60% stocks/40% bonds, and stocks had such a strong year that it's now 75%/25%. What specifically would you need to sell and buy to get back to the original 60/40 split?

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