Make a Bet to Reveal Your True Confidence

intermediate6 min readbusiness · psychology · decision_theory

Imagine placing a bet on a belief, with a clear outcome and something you value at stake. The exercise can expose a gap between a claim you readily make and a judgment you would rely on when being wrong has a cost.

THE IDEA

A BET CAN REVEAL HOW SURE YOU REALLY ARE

Imagine you’re talking with a friend who’s struggling to get her new catering business off the ground. You reassure her, “You’re amazing at this stuff! The only reason business is slow is because you’re just starting out. Everyone has trouble getting clients at first!”

She replies, “Thanks! I’m so glad you feel that way. Could you recommend me to your coworkers?”

Suddenly you feel hesitant. You recall her telling you about backing out of a job at the last minute . . . and you realize that you’ve never actually tasted her cooking . . . and you can’t help but ask yourself, “How sure am I, really, that she’ll do a decent job?”

When you were reassuring your friend a moment earlier, you weren’t lying. You just weren’t thinking about what you actually believed, because it didn’t seem to matter. But once there are actual stakes, and your reputation could take a hit if you guess wrong about your friend’s catering skill, your brain switches over from the goal “be supportive” to the goal “actually try to get the right answer.”

Evolutionary psychologist Robert Kurzban has an analogy for these two modes.11 In a company, there’s a board of directors whose role is to make the crucial decisions for the company—how to spend its budget, which risks to take, when to change strategies, and so on. Then there’s a press secretary whose role is to give statements about the company’s values, its mission, and the reasoning behind its decisions.

If a competitor starts gaining market share, the company’s press secretary might assure the public, “We’re not worried. Our brand has been America’s favorite for thirty years, and that’s not going to change.” However, if you were to sit in on a board meeting, you might find that behind the scenes, the board is taking the risk seriously and looking for ways to cut costs.

Imagine that the company sells toothpaste. The press secretary might assert confidently, “Our toothpaste whitens teeth better than any other brand on the market.” But suppose the board is approached by a dental school professor who says, “I’d like to do a study. I’ll assign groups of people to use one of the leading brands of toothpaste, without telling them which brand it is, and then I’ll measure how much whiter their teeth are. I’ll publish whatever results I get.”

If the board was truly confident that their toothpaste worked best, they would say, “Great—a chance to prove to the public that we’re the best!” But despite the press secretary’s assurances, the board might decide that they’re not confident enough they would win such a contest, and it’s not worth risking the embarrassment of losing.

The press secretary isn’t thinking about what’s true. He’s thinking about what he can get away with saying, what will present the company in the best light while still being at least sort of plausible. But the board is incentivized to form their best guess about the truth, because the company will thrive if they guess right and suffer if they’re wrong. The press secretary makes claims; the board makes bets.

The word bet might conjure up horse races and blackjack tables, but its meaning is far more general. A bet is any decision in which you stand to gain or lose something of value, based on the outcome. That could include money, health, time—or reputation, as in the case of your catering friend who wants your endorsement. So when you’re thinking about how sure you are, your answer will be more honest if you switch from thinking in terms of “What can I get away with claiming to myself?” to “How would I bet, if there was something at stake?”

Sometimes a project I’m working on seems hopeless. For example—just to pull a random, hypothetical situation out of thin air: “The book I’m writing is terrible and I should give up.” But how sure am I that I’m not just in a temporary funk? I’m 100% sure, my press secretary insists—but let’s ignore him, and pose a question to the board instead: “Suppose you would win $1,000 for correctly guessing whether you will still feel this way about your book a week from now. How would you bet?”

Now that there’s money on the line, I hesitate. I recall that I have felt pessimistic about my book, or some other project, many times in the past, and the dark cloud usually goes away in a day or two. It feels like a better bet to pick “Yes, I probably will feel better.” Going through that exercise doesn’t magically get rid of my bad mood, but it does take the edge off it. It’s useful to have proven to myself that I wouldn’t be willing to bet on this mood lasting, even though it feels like it will last forever.

A tip when you’re imagining betting on your beliefs: You may need to get more concrete about what you believe by coming up with a hypothetical test that could be performed to prove you right or wrong. For example, if you believe “Our computer servers are highly secure,” a hypothetical test might be something like this: Suppose you were to hire a hacker to try to break in to your systems. If they succeed, you lose one month’s salary. How confident do you feel that you would win that bet?

If you believe “I was being reasonable in that fight with my partner, and he was being unreasonable,” a hypothetical test might go something like this: Suppose another person, an objective third party, is given all of the relevant details about the fight, and is asked to judge which of you two is being more reasonable. If he judges in your favor, you win $1,000; if not, you lose $1,000. How confident do you feel that you would win that bet?

When to use it

Evaluating whether to endorse a product or person based on your true confidence.
Making major business decisions by replacing vague optimism with a bet scenario (e.g., security investments, marketing claims).
Assessing personal doubts by asking what you would bet on the outcome, to separate temporary emotions from genuine beliefs.
In a disagreement, specify what an impartial reviewer would examine and ask how you would bet on their judgment. Use any hesitation to identify facts or assumptions worth revisiting.

FROM THEORY TO EVERYDAY LIFE

In practice

Recommending a Friend’s Catering Business

You reassure a friend about her catering business, then hesitate when she asks you to recommend it to coworkers. Putting your reputation at stake prompts questions you had skipped: have you tasted her food, and can she reliably deliver?

Toothpaste Brand Claim

A company’s press secretary claims their toothpaste is best, but the board would hesitate to bet on a blind test, showing the gap between public claims and private beliefs.

Writer’s Doubt About a Book

The author feels their book is terrible, but a $1,000 bet on whether they’ll still feel that way next week reveals they don’t actually believe the feeling will last.

Server Security Assessment

Instead of simply saying the servers are secure, imagine losing a month’s salary if a hired hacker breaks in. What attack would count as a successful test, and what evidence supports your confidence?

Argument with Partner

Imagine an impartial person reviewing the details of an argument: you win $1,000 if they judge you more reasonable and lose $1,000 otherwise. Does your confidence change when you have to predict that judgment?

✳

A MOMENT TO REFLECT

Put it to work.

Think of a strong belief you hold. What would you be willing to wager on it, and what does that say about your actual confidence?
Identify a situation where you made a confident claim to others. How would your assessment change if your reputation or money were on the line?
When you feel a negative emotion (e.g., frustration, hopelessness) about a situation, imagine a bet on whether that feeling will persist. What does the exercise reveal?