.Cooper.
Silver
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Not a financial advisor. Personal experience only, not advice — do your own research.
START HERE
Buying is easy. Everyone loves buying. Selling is where people actually lose money — either panic-selling too early, or holding way past the point where the original thesis fell apart.
There's no perfect formula here, but there are actual reasons to sell, and there are bad ones. Knowing the difference is most of the battle.
Think of a position you're currently nervous about. Is your nervousness based on something that changed about the company, or just the fact that the price moved? Be honest this is usually the whole answer.
Long Term Investing 1.5 [When To Sell — Or When To Just Hold]
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The Hardest Skill in Trading
Buying is easy. Everyone loves buying. Selling is where people actually lose money — either panic-selling too early, or holding way past the point where the original thesis fell apart.
There's no perfect formula here, but there are actual reasons to sell, and there are bad ones. Knowing the difference is most of the battle.
Real Reasons to Sell
- The thesis you bought on is actually broken. Not "the stock is down," but the specific reason you owned it no longer applies.
- You need the money for something in your actual life. Rent, emergencies, real goals — that's a legitimate reason, not a trading failure.
- Rebalancing, because one position grew so large it's now a risk management problem, not a conviction problem.
- You found a significantly better opportunity and this one is now dead weight by comparison.
Bad Reasons to Sell
- It dropped 15% and it's scary. A drop alone isn't information — the reason behind it is.
- A headline said something dramatic. Refer back to Guide 1.1 — most of it is noise.
- It went up fast and you're scared of "giving back the gains." Selling a winner just because it moved isn't a strategy, it's anxiety.
- Boredom. Wanting to do something isn't a reason to sell something.
When to Just Hold
If nothing about the actual business has changed, the stock price moving isn't new information. Price is what the market feels today. Thesis is what's actually true about the company. Sell based on the second one, not the first.
SYSTEM CHECK
Think of a position you're currently nervous about. Is your nervousness based on something that changed about the company, or just the fact that the price moved? Be honest this is usually the whole answer.