Greed does not feel dangerous when you are winning. It feels like you finally understand the market.
Take Buckets From the Ocean
Book windfall profits. It is an ocean. Take a few buckets. If you try to take the whole sea, the tsunami can take you with it.
Greed turns windfalls into oversized bets. The goal is not to catch every dollar of upside. The goal is to book enough profit so compounding can continue.
Book windfall profits by a rule you set before greed arrives, because your judgment is least reliable when the account feels easy.
Story
I wrote this rule to myself in January 2021, near the peak of the meme-stock mania.
Never get carried away. Always book windfall profits. You can make a lot of money as long as the desire is to make decent money. The problem starts when you want to make all the money.
Then I wrote the line that stayed with me:
It is an ocean. Take a few buckets. If you try to take the whole sea, the tsunami can take you with it.
I was not quoting anyone. I was warning myself. My account had moved faster in a few months than it had moved in years of careful work. Some part of me knew the money felt too easy, and easy money has a way of leaving the same way it came.
The strange part is that I knew the rule before I fully obeyed it. I had made windfall gains. I knew I should book more of them. But selling a position that is still going up feels like leaving a party early. The screen keeps rewarding you. The account keeps growing. The mind starts saying, “Why take a bucket when the whole ocean is right there?” That is where the danger begins.
The next year reminded everyone that a bull market is not the same thing as genius. Froth burned off. Hot names broke. Portfolios that looked invincible started giving back gains. My own account gave up enough that rebuilding took years, and the rule I had written became less like advice and more like scar tissue.
The math is what makes the lesson unavoidable. A 20% loss needs a 25% gain to recover. A 33% loss needs about 50%. A 50% loss needs 100%. An 80% loss needs 400%. The deeper the drawdown, the harder the climb back becomes.
That is why windfalls matter. A paper gain is not the same as a booked gain. Until something is booked, it still belongs partly to the market. The market can mark it up. The market can mark it down. The market can take it back faster than it gave it.
I saw the other side too. There was one move where I booked most of a 42% gain in five days. I regretted it immediately. I thought I had sold too early. Then later that same day, my account still hit a fresh all-time high because the booked cash gave me room. I had taken a bucket, and the ocean was still there.
That is the part greed forgets. The market will probably be there next month. There will be another setup, another cycle, another chance. But if one oversized winner turns into a deep drawdown, the compounding machine gets damaged.
There is a saying my family used that captures the whole psychology: once you have been burned by hot milk, you blow on buttermilk before you drink it.
That is not paranoia. That is how survivors are made.
Meaning
Windfall profits are not for worship. They are for managing.
This chapter is really about greed. Not obvious greed, but the quiet kind that sounds like confidence. It tells you to hold just a little longer, size just a little bigger, and wait for just one more push. That voice is most convincing after you have already made money.
Greed does not usually feel like greed at the top. It feels like intelligence.When a position grows quickly, the emotional pressure changes. The investor starts thinking less about process and more about what could have been. The mind anchors to the highest number on the screen and begins treating an unrealized gain as if it already belongs to the investor.
But the market does not care what the account once showed. A gain is only fully yours when you book it. That does not mean selling everything. It means having a rule for trimming oversized winners, reducing risk, and turning some paper profit into protected capital.
The reason is simple: drawdown math is brutal. A 50% loss needs a 100% gain just to get back to even. An 80% loss needs 400%. That is why limiting losses often matters more than maximizing one big win.
Taking buckets from the ocean does not mean thinking small. It means respecting the size of the ocean.
Plain English
A drawdown is how far your account or position falls from its highest point. If your account reaches $100,000 and then falls to $70,000, that is a 30% drawdown.
The trap is that gains and losses are not equal. If you lose 50%, you do not need 50% to recover; you need 100%, because you are climbing back from a smaller base.
Booking a profit means selling part of a winning position so some of the gain becomes real cash instead of a number on the screen. A windfall profit is a gain that comes unusually fast or becomes unusually large. Windfalls feel amazing, but they also make judgment worse because the investor starts expecting the unusual to continue.
Position size means how much of your portfolio is in one trade or investment. If one winner becomes too large, it can quietly become the thing that damages the whole portfolio. The simple rule: when the market gives you an unusually large gain, book some of it by rule, not by emotion.
Framework
Before a position becomes huge, decide how profits will be booked.
- Define a windfall before it happens. Decide what counts as unusual: 25% in a week, 50% in a month, 100% in a cycle, or any gain that makes the position too large.
- Set the trim rule in advance. For example: sell one-quarter, one-third, or enough to recover original capital when the gain crosses your windfall level.
- Respect position size. If one holding grows beyond your comfort limit, trim it back even if the story is still exciting.
- Book profits on a rule, not a feeling. Feelings are loudest near tops. A rule protects you when greed sounds intelligent.
- Remember the recovery math. A 20% loss needs 25% to recover. A 33% loss needs 50%. A 50% loss needs 100%. An 80% loss needs 400%.
- Reset after a winning streak. After a big run, reduce position size back to normal on purpose. Risk grows quietly when confidence grows.
The rule is simple: take buckets from the ocean. You do not need every dollar of upside. You need enough gains kept safely so compounding can continue.