I sat down with Annie Duke: former professional poker player and author of the bestseller Thinking in Bets and Quit, to understand how the best decision-makers actually think.
Q: Annie, if you had to say it in one sentence: what’s the biggest mistake people make when thinking about decisions?
Annie: They judge decisions by how things turn out instead of how they were made.
And it sounds harmless, almost logical, but it’s the root of so much bad learning.
Keeping it simple: You can make a brilliant decision and get unlucky. You can make a terrible decision and get lucky.
If you don’t separate the two, you end up reinforcing luck and punishing good thinking.
You teach yourself the exact wrong lessons from your own life.
Q: That’s uncomfortable for people. We want outcomes to tell us whether we were right.
Annie: Of course we do. Outcomes feel concrete.
But imagine judging a poker player by a single hand:
They go all-in with the best odds.
Let’s say they have an 80% chance of winning…. and they lose!
Was it a bad decision?
No. It was a good decision with a bad outcome.
If you made that same play 100 times, you’d win 80 of them. That’s what makes it the right decision.
But people don’t think this way in life. They see one outcome and they judge everything by it.
“I hired this person and it didn’t work out, so I’m bad at hiring.”
Maybe. Or maybe you made a reasonable bet that didn’t work out this time.
Life works the same way as poker. We just pretend it doesn’t because we want the world to be less random than it is.
Q: So if outcomes are unreliable teachers, what should people use instead?
Annie: They should think in probabilities.
Not certainties. Probabilities.
Every decision is a bet on the future. That’s just true, even if we don’t like thinking about it that way.
So the question is never: “Will this work?”
The real question is: “How likely is this to work, and compared to what?”
That framing alone changes how carefully you think.
Because now you can’t just say “I think this will work.” You have to get specific.
“I think there’s a 60% chance this marketing campaign hits our targets.”
“I think there’s a 70% chance this hire works out.”
Suddenly you’re forced to actually examine your reasoning instead of just going with your gut and hoping.
Q: But most people don’t think in probabilities. They think in stories. Why is that?
Annie: Exactly. Humans are natural storytellers.
After something happens, we tell ourselves a clean, causal story (lol):
- “This worked because I’m smart.”
- “This failed because the idea was bad.”
- “This person succeeded because they’re talented.”
But those stories ignore randomness.
They ignore all the things outside your control that contributed to the outcome.
The problem is stories feel satisfying. They give us closure.
Probabilities keep us in uncertainty, which is uncomfortable.
Q: Is that why smart people can stay wrong for so long?
Annie: Yes.
Intelligence doesn’t protect you from bad thinking.
In many cases, it makes it worse.
Because smart people are better at rationalizing.
Better at defending their beliefs.
Better at constructing convincing explanations after the fact.
If you’re intelligent and you believe something, you can build an incredibly sophisticated argument to support it.
You can find evidence. You can dismiss counterarguments. You can make it all sound airtight.
And everyone listening, including you, thinks: “Wow, that’s really well-reasoned.”
But here’s the trap: You’re not trying to find truth. You’re trying to defend the story you already believe.
In a way, Sales is like this. A salesperson is finding the best angle that defends a belief, regardless of whether that’s the best decision for the prospect to make.
Q: So intelligence becomes a tool for self-deception. How do you protect yourself from your own intelligence?
Annie: You build systems that force you to be honest.
Because you can’t trust yourself. Your brain is too good at lying to you in ways that feel like truth.
Here’s what actually works:
Before you make a big decision, write down:
- What you think will happen
- Why you think it will happen
- How confident you are (as a percentage)
- What would prove you wrong
That last one is critical. If you can’t name what would change your mind, you’re not thinking, you’re just attached to being right.
Then, when the outcome arrives, you go back to what you wrote.
You’re not rewriting history based on what happened.
You’re comparing reality to your prior beliefs.
That’s how learning actually happens.
Most people skip this step. They just move on to the next decision, carrying all their biases with them.
Q: So how should people think about uncertainty without becoming passive? Because there’s a difference between humility and paralysis.
Annie: Great question.
Uncertainty doesn’t mean inaction. It means probabilistic action.
You’re never going to have perfect information. Never.
If you wait until you’re certain, you’ll never move.
But here’s the shift: Instead of asking “Am I sure?” you ask “Given the odds and the stakes, is this worth betting on?”
Sometimes a 50/50 bet is worth taking if the upside is huge and the downside is manageable.
Sometimes even a 70% chance isn’t worth it if the downside would destroy you.
The question isn’t “Am I certain?”
The question is “Given what I know, given the probabilities, given what’s at stake, is this a good bet?”
And then you act.
You make the best decision you can with the information you have, knowing you might be wrong, but also knowing that waiting for certainty is itself a decision, and usually not a good one.
Q: Let’s make this practical. How does probabilistic thinking apply to business and sales?
Annie: Let’s take sales since that’s what a lot of your readers do.
Most salespeople think: “Did I close this deal or not?”
Binary. Yes or no. Win or loss.
But probabilistic thinking looks completely different.
Now you’re not trying to close everyone, you’re trying to improve the odds with each interaction.
You start to notice patterns:
- “When I lead with social proof, my close rate goes from 30% to 45%.”
- “When I talk to decision-makers instead of gatekeepers, my odds double.”
- “When I follow up within 24 hours, I’m 20% more likely to close than if I wait three days.”
You’re building a mental model of what actually moves the needle.
And here’s the psychological shift: You stop taking individual losses personally.
You’re playing a probabilistic game, and you’re getting better at the odds with each iteration.
And, by the way:
A sales call can be GREAT, even with a bad outcome.
Again, judge the process being used, not the outcome.
Actually, the best way to assess the quality of salespeople is by seeing their best unsuccessful cases, which also avoids survivorship bias.
Q: That reframe is powerful. But why is “expected value” more important than being right?
Annie: Because life isn’t about maximizing how often you’re right.
It’s about maximizing the value of your outcomes over time.
Let me give you a concrete example that makes this crystal clear:
Option A: 90% chance of making $1,000
Option B: 10% chance of making $100,000
Most people instinctively pick Option A because they want to “be right” and 90% feels safe.
But let’s do the math:
- Option A expected value: 0.9 × $1,000 = $900
- Option B expected value: 0.1 × $100,000 = $10,000
Option B is worth more than 10x as much, even though you’ll “lose” 90% of the time.
This is how the best investors think. How the best entrepreneurs think.
They’re not trying to win every bet. They’re trying to make bets where the expected value is massively in their favor, even if most individual attempts fail.
Venture capitalists know nine out of ten investments will fail. But the one that hits can return 100x.
That’s not lucky. That’s expected value thinking.