A beginner and a chess grandmaster can look at the identical board and see two different games. The beginner spots a move. The grandmaster sees a web of possibilities — not just one future, but dozens, each move branching into further decisions and further branches beyond that.

Same pieces. Same board. What separates them is how many future scenarios each one can hold in their head before committing to a move.

That got me thinking: what if decision-making outside of chess works the same way?

What if some of our worst outcomes aren’t the result of bad choices at all, but of not imagining enough futures before we made the choice?

Business history is full of sharp, capable people who got boxed in by a single version of what was coming. Kodak assumed film would stay king. Blockbuster assumed people would keep driving to a store to rent a movie. Theranos convinced seasoned investors and executives that a blood-testing breakthrough already existed. Anna Delvey convinced bankers, hoteliers, and New York’s social elite that she was a wealthy German heiress.

Different people, different industries — the same underlying failure. At some point, everyone involved stopped asking, “What else might be true here?”

That question might be one of the most useful ones we can keep in our back pocket. Because every meaningful decision is really a bet on a future we’re imagining — and it’s rarely the future itself that traps us. It’s the assumptions we make about it.

Picture being able to preview a handful of possible outcomes before you commit to anything big: one where the plan unfolds exactly as expected, one where your central assumption turns out to be false, one where an unplanned opportunity shows up, and one where quiet costs slowly eat away at the upside.

You still won’t know which future actually arrives. But you’ll walk in better prepared, because you looked at more than one.

After enough surprises, miscalculations, and reminders that life doesn’t move in straight lines, I started handling important decisions differently. I built myself something like a filter.

Not to be pessimistic. Not to force relentless optimism either. And not because every surprise is avoidable — some aren’t.

I do it because I’d rather see clearly before I commit to anything. I ask myself questions designed to push past my first read of a situation, test my assumptions, and consider more than one version of how things could unfold.

Some surprises really are just part of being alive. But others could have been caught earlier — if I’d slowed down, asked sharper questions, or looked from more than one angle. Those are the ones worth trying to catch.

Not by controlling everything. By preparing for more of it.

Before a big decision now, I run what I think of as a multiple-futures check. Instead of asking “what should I do,” I ask: “what futures open up if I choose this path?”

Then I work through questions like:

• What could this look like a year from now?
• What doors open?
• What doors close?
• What costs am I not seeing yet?
• What am I assuming, without realizing I’m assuming it?
• What information am I missing?
• What happens if my central assumption is wrong?
• What would prove me wrong, if I was?
• What could catch me off guard that I haven’t planned for?
• Which risks could I lower starting today?
• Which of these futures would I actually want to live in?

Then I do it again for the next option. And the one after that.

Not to talk myself out of deciding. Not to manufacture fear. Not to catastrophize every path. Just to widen the lens before I lock anything in.

Preparing for multiple outcomes isn’t pessimism, and it isn’t naive optimism either — it’s an honest attempt to stand still for a moment and actually look in more than one direction.

Our lives add up to the choices we make, and every choice is shaped by the future we happened to picture at the time. Maybe the quality of a decision has less to do with finding the “right” answer and more to do with how many futures we were willing to consider before choosing.

Maybe wisdom isn’t about predicting what happens next. Maybe it’s having the humility to admit the future could unfold in ways we haven’t even thought of yet.

So before your next big decision, pause. Trade certainty for curiosity. Trade assumptions for questions.

Look past the future you’re hoping for. Look past the one you’re afraid of. Go looking for the ones you haven’t considered at all — because the future can’t be observed directly, only explored.

And sometimes, the smartest decision starts with a single question: what future haven’t I considered yet?