Psychology Trap

Why Do I Always Buy High and Sell Low

Noticed a painful pattern of making decisions at the worst moments

What the Masters Would Say

Buying high and selling low is the single most common pattern in retail investing, and it is not because individual investors are unintelligent. It is because the human brain is wired for survival in ways that are systematically counterproductive in financial markets. Understanding why you do this is the first step toward stopping it.

The cycle works like this: a stock or market rises, generating excitement and media coverage. You see others making money and feel the fear of missing out. You buy near the peak because the momentum makes it feel safe. Then the market declines, and fear replaces greed. You watch your portfolio shrink, and the pain of losses (which research shows is psychologically twice as intense as the pleasure of equivalent gains) eventually becomes unbearable. You sell near the bottom to stop the bleeding. Then the market recovers without you.

Warren Buffett diagnosed this perfectly: "Be fearful when others are greedy, and greedy when others are fearful." This is easy to say and extraordinarily difficult to do because it requires acting against your deepest emotional instincts. When everyone is buying and feeling confident, your brain interprets that social consensus as safety. When everyone is selling and feeling panicked, your brain interprets that as danger. In both cases, your brain is giving you exactly the wrong signal for investing.

Benjamin Graham described the market as "a voting machine in the short run and a weighing machine in the long run." When you buy high, you are participating in a popularity contest. When you sell low, you are letting Mr. Market's temporary depression dictate your decisions. The intelligent investor does the opposite: they use the voting machine's errors as buying opportunities.

Howard Marks observes that superior investing requires "second-level thinking" -- going beyond the obvious consensus to ask "what does the crowd expect, and how might reality differ?" When a stock is at its highs and everyone is bullish, second-level thinking asks: what could go wrong that the consensus has not considered? When a stock is at its lows and everyone is bearish, second-level thinking asks: what could go right?

Here is a practical system to break the buy-high-sell-low cycle:

Your Action Plan

1. Automate your investments with regular monthly contributions regardless of market conditions. Dollar-cost averaging removes the timing decision entirely and naturally leads you to buy more shares when prices are low.
2. Create a written investment policy statement that defines exactly what you will buy, at what valuations, and what would trigger a sale. Make all decisions based on this document, not on how you feel.
3. Implement a mandatory 48-hour waiting period before any trade that is motivated by emotion rather than analysis.
4. Track your emotional state when making investment decisions. If you feel excited about buying, that is often a contrarian sell signal. If you feel terrified about holding, that is often a contrarian buy signal.
5. Study market history. Every panic felt like "this time is different" at the time. None of them were. Understanding this pattern intellectually is the first step toward overriding the emotional response.

The Bottom Line

The goal is not to eliminate emotions -- that is impossible. The goal is to build systems that prevent emotions from driving your investment decisions.

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  • Last Updated: 2026-02-12
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