What are the odds?
How to stop guessing and start making smarter bets in everyday life...
Imagine I told you a basketball team was going to outperform their opponent in the following stats:
Field goal percentage
Free throw attempts
Assists
Fewer turnovers
Steals
And then I told you that teams who win all five of those categories in NCAA tournament games are 335–0. Undefeated.
Would you bet on that team to win?
If you said yes—congrats, you picked the statistically obvious favorite.
If you said no—you’d be right… for the first time in history.
What happened? Well, the 336th team to check all five boxes lost. And it reminds us: the improbable isn’t impossible.
Most of us throw around words like “always,” “never,” “probably,” “maybe,” “likely,” without any real sense of what we mean. We speak in probabilities—but we rarely pause to think in them.
That’s why I love this week’s question:
What are the odds?
It’s a way of forcing ourselves to pause, evaluate, and quantify—however roughly—the likelihood of something happening. It’s a gut check, an intellectual honesty alarm, and a decision-making compass all rolled into one.
Annie Duke, former professional poker player and author of How to Decide, talks about how this kind of statistical thinking can help us better navigate uncertainty. In the book, she walks through a simple but powerful decision-making tool using a common dilemma: whether or not to accept a job offer.
First, list out your potential outcomes—not every possible multiverse outcome, but the likely handful that matter.
Then, weigh those options against what you know about yourself:
I hate cold weather
I love working
I’m close with my family
Looking at a job that’s in a cold climate, with long hours and far from home? Well, what are the odds you’ll be happy in Outcome #1? Low. Maybe 10%.
Continue assigning percentages and eventually there will be an option that begins to emerge as the most statistically probable.
You’re not just guessing. You’re being thoughtful. You're putting numbers to your instincts. You're asking: would I bet on this?
That small shift—from vague prediction to calculated wager—changes everything. Because when you ask “What are the odds?” you stop pretending you know and start realizing you’re forecasting. You’re building self-awareness. You’re stress-testing your assumptions.
It’s a question that sits at the intersection of statistics and soul-searching.
So the next time you catch yourself saying “probably,” stop.
And ask: How probable?
Would I bet on it?
And if I wouldn’t… why am I acting like it’s guaranteed?
Because in a world where even the surest bets can lose on the 336th try, the people who make the best decisions aren’t the ones who know—they’re the ones who ask.
And what if after all of this work, you’re still wrong?
"What makes a decision great is not that it has a great outcome. A great decision is the result of a good process."
(Annie Duke, How to Decide)
Did you follow a thoughtful process to arrive at your decision?
Yes? Then congratulations, you can be confident that you made the right choice and this time it just didn’t work out. Refine your process for the next decision and try again!
No? You were guessing. So this was all a matter of chance anyway. Come back next time with the right process.
The next time you’re facing a big decision, don’t just hope and guess.
Ask what the odds are.
And then—keep asking.
Keep Asking,
Kyle