Source
When this applies
when deciding whether to exit any investment, product line, or committed position after it has moved up or down in price
The takeaway
Base sell decisions on reassessing the original investment thesis and comparing current opportunity cost, not on the emotional discomfort of a price move in either direction.
Why it works
Most people sell to manage regret (fear of losses evaporating or growing) rather than reasoning about fundamentals and opportunity cost, which confuses price action with intrinsic value change and causes systematic premature exits from the rare compounding winners that drive most lifetime returns.
One level up
Avoiding regret is a powerful but largely value-destroying motivator in decision-making; decisions should be reframed around the forward-looking 'unbuy' question instead.
Where it stops holding
This stops working when the position has a capped upside (e.g., most bonds/credit, where you can't get more than 100 cents on the dollar) — in capped-upside assets, taking profits on price strength is more rational.
Detail
rule: Reframe the selling decision as a fresh 'unbuy' decision: would I buy this today at this price, given what I now believe about the future and my opportunity cost?
threshold: If a rare asset can genuinely compound value at a high rate for decades (e.g., ~20%/year), its fair value compounds too, so price appreciation alone (even 'looking overvalued') doesn't justify selling — something fundamental has to change.
rationale: Most people sell because they're up (fear profit will evaporate) or because they're down (fear further loss) — neither reason has anything to do with the business itself.
In their words
My view on selling is consistent with the general way that we talked about the value and sort of growth dichotomy, which is that what matters in investing is really deeply understanding what you own and why you are making the investment and what you're playing for.