Strategy and Power

Trade Outside the Box

by Brent Donnelly

22 rips · Deciding under uncertainty · Seeing clearly · Negotiating

Trading and decision-making — veteran FX trader Brent Donnelly borrows from poker, psychology and physics to show how professionals think about what others think, read market tells, size risk and pick games they can win.

Mechanisms (4)

mechanism #1283

Forecasters herd to protect their careers

Economists shade their forecasts toward the consensus, so the range of published estimates is narrower than the range of real outcomes.

"If you put a forecast way above everyone else and the number comes in low, you look stupid. If you submit a forecast just a bit higher than everyone else, then no matter how strong the number is, you look smart!" "Herding around the mean is rational if you want to avoid looking stupid or getting fired, but as a market professional you need to be aware that the data is not clustered the way the forecasts imply."

Why it matters

Economists shade their forecasts toward the consensus, so the range of published estimates is narrower than the range of real outcomes. Actual surprises are bigger and more frequent than the clustered forecasts suggest.

Use when: You're treating a tight consensus of expert forecasts as a measure of real uncertainty.

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mechanism #1286

Watch for the market eating an Oreo

In Rounders, Teddy KGB eats the Oreo only when his hand is strong.

"One of the best tells in markets is a market that fails to react to good or bad news." "More often than not, a market that doesn’t respond to clearly good or bad news is going to trend in the opposite direction for the next 24 to 48 hours."

Why it matters

In Rounders, Teddy KGB eats the Oreo only when his hand is strong. Donnelly's top market tell is a price that ignores the news. It suggests stronger hands are using the headline as cover to exit.

Use when: Something that should have moved the other side didn't, and you're inclined to ignore it.

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mechanism #1287

Find the player on tilt

Emotional players make predictable, oversized mistakes, and that is when the calm player extracts the most.

"In poker, the dream scenario is you run into a player on tilt. They are easy to read, they play loose, and they repeatedly put their chips in with the second or third-best hand."

Why it matters

Emotional players make predictable, oversized mistakes, and that is when the calm player extracts the most. Donnelly asks the same of whole markets: can you tell when the crowd itself is on tilt?

Use when: The other side is visibly emotional and you're tempted to match their energy.

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mechanism #1292

Weight their view by how wide they quote

Donnelly quotes Agustin Lebron's example from The Laws of Trading.

"All other things equal, you should think that Jo only has 40% (0.20/0.50) of the confidence in her fair value as you do in yours."

Why it matters

Donnelly quotes Agustin Lebron's example from The Laws of Trading. Your rival's price is 0.50 wide and yours is 0.20, so blend the two fair values weighted by confidence. You end up with a better estimate than blindly trusting either one.

Use when: The other side's number differs from yours and you have to decide how much to move.

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Arguments (3)

argument #1281

The calmest mind wins, not the biggest brain

Markets keep swinging between fear and greed, and Donnelly no longer believes first-order fundamentals make money.

"The money is made by those who can get outside themselves to combine second-order thinking with ultrarational behavior to forecast and exploit the emotional, irrational, and sometimes predictable behavior of the market hivemind."

Why it matters

Markets keep swinging between fear and greed, and Donnelly no longer believes first-order fundamentals make money. His Principle 10 is that the most rational trader wins. Intelligence and hard work don't protect anyone from the emotions they share with the crowd.

Use when: You're relying on being smarter than the competition in a field driven by crowd emotion.

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argument #1293

Don't let adverse selection paralyze you

Most trades in liquid markets are hedges and routine flows with no hidden information.

"If adverse selection dominated, nobody would ever trade because everyone would be afraid that everyone else has better information than they do." "If you know what you are doing, you will be adversely selecting others much more often than you are adversely selected yourself."

Why it matters

Most trades in liquid markets are hedges and routine flows with no hidden information. The danger is real in thin markets, where the counterparty likely knows more and exiting is expensive. Donnelly says to fear it where it applies and nowhere else.

Use when: You're worried that anyone willing to deal with you must know something you don't.

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argument #1299

Growth is slow and linear

Bank interest compounds.

"There is a meme that says: If you improve by 1% per day, you will be 37.78 times better after one year. It’s a nice thought, but it’s wrong."

Why it matters

Bank interest compounds. Push-ups don't: a 1% daily increase would mean 770 million push-ups in five years. Expecting exponential personal gains sets people up to quit when progress turns out slow and lumpy.

Use when: You're discouraged that skills or results aren't compounding the way the self-help math promised.

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Concepts (4)

concept #1278

Choose the face the judges will choose

Donnelly uses Keynes' contest to explain why buying the cheapest stock on a spreadsheet can lose.

"Keynes asks us to imagine a newspaper which holds a contest where readers are rewarded for choosing which contestant will be chosen by the most other readers." "The task is not to choose the most beautiful woman, but instead to choose the woman others will think is most beautiful."

Why it matters

Donnelly uses Keynes' contest to explain why buying the cheapest stock on a spreadsheet can lose. Prices move on what other participants will believe next, and that is a different question from what's true.

Use when: You're right on the merits and need to predict how a crowd, market or committee will actually decide.

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concept #1288

Falling volatility says the move is tired

Even if prices keep inching up, shrinking swings signal that the forced buying or selling behind the move is done.

"When a market enters a tight trading range after a significant move and volatility begins to contract sharply, it tells you that the order imbalance in the market has been rectified, and a more stable short- term equilibrium has been found."

Why it matters

Even if prices keep inching up, shrinking swings signal that the forced buying or selling behind the move is done. Donnelly reads it as a clue that the trend is nearly exhausted.

Use when: A trend is still going but the swings around it have gone quiet.

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concept #1289

The group average isn't your average

If 100 people play Russian roulette once for $10 million, the group's average is attractive.

"The simple definition of an ergodic system is one where the expected value of an activity performed by a group is the same for an individual carrying out the same activity over time." "Nobody would choose to play this game 100 times in a row because the expected outcome is almost certain death."

Why it matters

If 100 people play Russian roulette once for $10 million, the group's average is attractive. One person playing 100 times dies. Donnelly applies this to all-in betting: a positive average can still ruin the individual who repeats the bet.

Use when: A bet looks good on average and you'll be making it over and over with the same bankroll.

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concept #1296

Count the mental capital a bet consumes

Long, stressful, attention-hungry positions drain focus from everything else.

"Mental capital is an important, underappreciated and finite resource." "This sort of trade could be mathematically positive EV but be so mentally taxing that even when it works, it has cost you more than you earned."

Why it matters

Long, stressful, attention-hungry positions drain focus from everything else. People tend to bail out of them early just to relieve the anxiety. Donnelly counts that drain as a real cost of the position.

Use when: A project looks good on paper and would occupy your head every day for months.

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Evidence (2)

evidence #1279

The Smarties test for adults

A child who has just seen pencils in the Smarties tube assumes a friend will know too.

"Younger children, or those without a fully developed Theory of Mind, will say that James will say: “pencils,” because they are unable to separate their own knowledge from someone else’s perspective." "Adults in financial markets often operate like the children in the Smarties Test. They think that everyone sees the world the way they do."

Why it matters

A child who has just seen pencils in the Smarties tube assumes a friend will know too. Donnelly sees the same error in traders who can't model what others believe. They keep insisting on their own view while the market moves on everyone else's.

Use when: You're sure the other side must see what you see.

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evidence #1290

Starting points decide the reaction

In 2025 the US and UK raised spending and were punished, while Germany did the same and rallied.

"We saw opposite market reactions to identical policy announcements because the market viewed the U.S. and U.K. starting points as fragile, and Germany’s initial conditions as robust."

Why it matters

In 2025 the US and UK raised spending and were punished, while Germany did the same and rallied. Debt was 130%, 100% and about 60% of GDP. The same news means different things depending on where you start.

Use when: You're predicting the effect of a move by copying what happened when someone else made it.

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Questions (1)

question #1284

Am I doing this for fun or for money?

Donnelly says position size should come from a calculation.

"Ask yourself regularly: Am I trading for fun, or to make money?" "If you find yourself putting on the “correct” position size and then 15 minutes later doubling it because you’re bored… You’re trading for excitement, not to make money."

Why it matters

Donnelly says position size should come from a calculation. Doubling it out of boredom signals that excitement is driving the decision. Being honest about the motive is the first step to separating the two.

Use when: You notice yourself raising the stakes on a decision because the safe version feels dull.

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Definitions (1)

definition #1291

Narrative contagion

Stories start near a truth and then morph into caricatures as more people tell their own versions.

"Narrative contagion is the process whereby a story shared by one person or organization prompts others to share their own stories, spreading narrative themes organically through a community." "Markets are social systems, not machines that take in fundamental information and spit out logical prices."

Why it matters

Stories start near a truth and then morph into caricatures as more people tell their own versions. Donnelly's example is GameStop, which began with a few Reddit posts. The spread drives sentiment and price. His advice is to watch dispassionately while the crowd goes mad.

Use when: A story about your industry or company is spreading faster than the facts behind it.

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Passages (1)

passage #1282

Worry about what you're doing

Tom Brady wanted to leave Michigan because he barely got practice reps.

"“Brady, I want you to stop worrying about what all the other players on our team are doing. All you do is worry about what the starter is doing, what the second guy is doing, what everyone else is doing. You don’t worry about what you’re doing.”"

Why it matters

Tom Brady wanted to leave Michigan because he barely got practice reps. His coach pointed his attention back to the one thing he controlled. Donnelly uses the story for his Serenity Prayer principle: separate what you can change from what you can't.

Use when: You're frustrated by others getting the opportunities and have stopped working on your own game.

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Rules (6)

rule #1280

Early is the same as wrong, and so is late

Being right too soon burns money, attention and credibility while you wait.

"There is a market aphorism that says: Early is the same thing as wrong." "You underperform as you wait for your dream trade to come true and eventually get fired three weeks before it finally works. Then again, it’s important to remember that late is the same thing as wrong."

Why it matters

Being right too soon burns money, attention and credibility while you wait. Donnelly says "it's come too far, too fast" is a poor reason to bet against a move. You need a specific reason the trend will turn now.

Use when: You're about to bet against a trend just because it has gone a long way.

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rule #1285

Avoid ruin first, maximize returns second

Getting stopped out on a trade that later works is a cost of staying in the game.

"Principle 14: Avoid risk of ruin first. Maximize returns second. If you blow up, there will be no returns."

Why it matters

Getting stopped out on a trade that later works is a cost of staying in the game. Donnelly treats it as luck that evens out. A loss that ends the game never evens out, so survival constraints come before upside.

Use when: A high-return plan carries a small chance of wiping you out.

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rule #1294

The too-hard pile

Donnelly learned just enough short-term interest rate trading to read central bank expectations and skipped the rest.

"I don’t shy away from hard topics, but if the answer to the following three questions is yes, I put the topic in the too hard pile. 1. Not particularly interesting. 2. Not critical to developing an edge in my business. 3. Complex and time consuming to learn."

Why it matters

Donnelly learned just enough short-term interest rate trading to read central bank expectations and skipped the rest. Years spent mastering it would barely have moved his career. A deliberate skip list frees time for what builds an edge.

Use when: You feel you should master everything adjacent to your work.

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rule #1295

Match the analysis to the time horizon

Donnelly's early write-ups paired analysis suited to a month or a year with trades that could be stopped out in about a day.

"I would write a big piece about Australian Terms of Trade and the employment situation in Australia and so on... And then go long AUDUSD with a stop loss 1% away." "When trading (and investing), your time horizon must match your analysis."

Why it matters

Donnelly's early write-ups paired analysis suited to a month or a year with trades that could be stopped out in about a day. Slow fundamentals can't protect a fast position, so the timeframe of the plan and of the evidence must line up.

Use when: Your argument is about the long run and your commitment can be shaken out next week.

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rule #1297

Stack new edges before the old one dies

Donnelly's fast lead/lag correlation trades in FX were steady money in the 2000s.

"The more profitable my strategy, the more likely someone else will discover it. Keep stacking new ideas on top of old ones. When the old ones stop working, the new ones will pay the bills."

Why it matters

Donnelly's fast lead/lag correlation trades in FX were steady money in the 2000s. Then algorithms and other traders caught on and the trade disappeared. Profitable methods attract competition and get arbitraged away, so the next one has to be built while the current one still pays.

Use when: Your current advantage is working well and you've stopped developing a replacement.

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rule #1298

Your reputation is a teacup

Donnelly opens with Ben Hunt's line and notes how old connections keep resurfacing.

"“Your reputation is like a teacup. Once it’s broken, it’s almost impossible to put back together.”" "All your actions accumulate in the long run. Be nice to the person who sweeps the floors in your office."

Why it matters

Donnelly opens with Ben Hunt's line and notes how old connections keep resurfacing. He says people remember how you treated them decades later. His rules: treat PAs and brokers the way you treat managing directors, and volunteer for the holiday shift. Small acts compound into a reputation.

Use when: Cutting a corner or snubbing someone junior looks free in the short run.

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