Stop expecting certainty from a probabilistic world
We love copying what works for other people.
Someone’s fitness routine. Someone’s diet. Someone’s “winning” strategy. Industry best practices. The formula your old company used. The approach you swear by because it worked once before.
It feels safer than facing a blank page. Than having to go through all the mistakes on your own not even sure if you'll end up in the right place.
In a world of infinite possibilities, uncertainty is heavy. A proven playbook lightens the load.
But this often backfires.
We mistake someone else’s map for our terrain.
We forget that strategy lives or dies by context - your personality, resources, constraints, other people, timing, mood, health, environment, energy, opportunities, partners, mindsets and beliefs we don't see. When context shifts, the old strategy quietly stops working… and we often don’t notice until pain of failure makes it obvious. (And even then we are often stubborn enough to continue)
This failing rigidity is the cost of outsourcing our thinking.
But there's a way to combine the best of both worlds - having a better chance of success with proven strategies, and a better system for flexible application that sees the context as well, and considers multiple options.
THINKING IN PROBABILITIES (As poker players would🃏)
A better way is defining success upfront, defining early signs of being on the right/wrong track, and learning to think in probabilities.
Annie Duke (world's poker champion) teaches a simple process that I'm coming back to again and again in business and when coaching clients:
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List all the possible outcomes (not only the ones you want).
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Clarify your preferences based on values and goals.
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Estimate the likelihood on a 1–5 scale (1 = nearly impossible; 5 = almost a guarantee).
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Identify the possible payoffs, positive and negative for each option.
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Compare.
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Decide.
No fantasy guarantees. Just probabilities, payoffs and preferences.
And with tools like ChatGPT, you can interrogate your assumptions even further, reduce bias, and get a third-person viewpoint when your emotions get in the way.
I used this with a client this week, helping them navigate a difficult negotiation.
I suggested to consider:
“What’s the worst possible outcome here?
And if it happens, what’s your plan?”
Once he answered that, he relaxed. Because he realized: he already had a path even in the worst-case scenario. His brain stopped catastrophizing. He could think clearly again about how to make better outcomes more likely to happen.
It's like preparing soil and all the conditions for your crop to thrive, knowing in advance, that the weather isn't a guarantee.
Different things happen.
When you prepare for the worst, and design around it, you give yourself the freedom to aim for the best.
It’s the same logic behind healthy meal prep. You don’t wait for willpower. You set up conditions. You remove friction. You skew the odds. And on the worst day you end up chewing broccoli because that's what you prepped for🥦
Most meaningful decisions in life aren’t certainties. They’re bets.
The question isn’t “Will it work?”
The question is:
“What can I do today to tilt the probabilities in my favor?”
