What the Masters Would Say
Holding a losing stock creates immense psychological pressure that clouds your judgment. The sunk cost fallacy -- the feeling that you have already invested too much to walk away -- makes you think "I have already lost this much, I cannot sell now." But here is the uncomfortable truth: the stock does not know what you paid for it, and your purchase price is completely irrelevant to its future prospects.
Peter Lynch captured this perfectly: holding your losers while selling your winners is like watering the weeds and pulling the flowers. It is the opposite of what a rational gardener would do, but it is exactly what most investors do because losses hurt approximately twice as much as equivalent gains feel good. This psychological asymmetry -- known as loss aversion -- pushes you to avoid crystallizing losses, even when holding guarantees worse outcomes.
Warren Buffett's advice is characteristically direct: when you find yourself in a hole, stop digging. If a stock is underperforming because the business is deteriorating, holding it and hoping for a recovery is not a strategy -- it is wishful thinking. Hope is not an investment thesis.
Charlie Munger adds a critical nuance: one good reason mixed with several bad reasons for holding a position still makes it a bad investment. You need to be brutally honest about whether your reasons for holding are based on analysis or on emotion. The most common emotional reasons are: "I will sell when I get back to break-even" (anchoring bias), "the stock has to go up eventually" (mean reversion fallacy), and "I have already lost so much, what is a little more" (sunk cost fallacy).
Howard Marks teaches that the willingness to accept losses is one of the key differentiators between great investors and mediocre ones. Great investors cut losing positions quickly and reallocate capital to better opportunities. Mediocre investors hold losers indefinitely, hoping for a miracle while their capital is locked up and unproductive.
Here is a framework that removes emotion from the decision:
Your Action Plan
2. Write down the original reason you bought the stock. If that thesis is no longer valid -- the competitive advantage has eroded, management has failed, or the industry has changed -- the position should not be in your portfolio.
3. Set a clear rule: if a company misses your expectations three consecutive times -- on earnings, revenue growth, or management execution -- sell automatically.
4. Accept that the loss already occurred the moment the business deteriorated, whether you realize it on paper or not. Selling does not create the loss -- it acknowledges it.
5. Redirect the proceeds to your highest-conviction current idea.
The Bottom Line
Cut your losses with discipline, or they will cut your returns for years.
Citation Traceability
- Canonical URL: https://keeprule.com/en/scenarios/should-i-sell-losing-stock-or-hold
- Language Served: en (requested: en)
- Last Updated: 2026-02-12
Want Deeper Analysis?
Copy this scenario as an AI prompt. Paste it into ChatGPT, Claude, or Gemini for personalized analysis
Principles That Apply
"Should you find yourself in a chronically leaking boat, energy devoted to changing vessels is likely to be more productive than energy devoted to patching leaks."Read Full Principle →
"Sell when the story changes."Read Full Principle →
"It is remarkable how much long-term advantage people like us have gotten by trying to be consistently not stupid."Read Full Principle →
Explore More Scenarios
Browse all 30 investing dilemmas and discover what legendary investors would do in each situation.
View All Scenarios