I was sitting with a VP of Product, working on next year’s roadmap. As he was laying down features one by one on a timeline, I told him that we should treat it differently.

In an attempt to take the conversation to a more strategic place, I suggested looking at it from the future. Where does the company actually need to be a year from now? What business outcomes matter most? What gaps stand in the way? What assumptions are we making about customers, the market, and the product itself?

He stopped for a moment and then said: “I don’t know what the future will be like. So how can I plan for it?”

It’s an honest question. And on the surface, it sounds reasonable. The world keeps changing, markets shift, priorities move, and plans rarely survive first contact with reality. But hidden inside that sentence is an assumption that quietly turns uncertainty into paralysis.

If you’ve ever felt that the future is simply too overwhelming to plan for, this is where the work actually begins.

Unknown, not unbounded

Not knowing how the future will unfold often gets translated into a much stronger claim: that anything might happen. That the space of possibilities is endless.

And in a purely theoretical sense, that’s true. There are infinitely many ways the world could evolve. But we don’t live in theory. In reality, out of all those possible futures, only a very small number are actually plausible.

Markets don’t branch out in every direction at once. Companies have momentum, constraints, and histories. Customers adopt new behaviors gradually, not randomly. Technologies create new options, but they also narrow the field. When you look closely, the future usually resolves into a handful of realistic paths, not an open-ended cloud of maybes.

When you stop asking “what might possibly happen?” and start asking “which few futures are actually worth taking seriously?”, you can start thinking about how to prepare for them, where you want to be strong, and how you plan to win.

That’s when uncertainty stops being overwhelming and starts becoming something you can work with.

The futures that matter most

This is usually the moment where people expect a framework, a matrix, or a prediction exercise. But narrowing the future doesn’t start with tools. It starts with judgment. The question isn’t which future is most likely to happen, but which futures would fundamentally change what you need to do, what you need to be good at, and where you could realistically win.

Some futures are noisy but irrelevant. Others are theoretically possible but wouldn’t meaningfully alter your direction. The futures that matter most are the ones that would force different choices. Different investments. Different tradeoffs. When you name those few futures explicitly, you give yourself something concrete to work with, without pretending to know which one will actually materialize.

If you want a bit more structure, or you find it hard to answer these questions on your own, it can help to look at the future from a few deliberate angles. Not as predictions, but as ways to surface what really matters.

• What are you most afraid of? If that scenario materializes, what would it actually mean for your business and your product?
• What is the best-case scenario you can realistically hope for? What would need to be true for that future to unfold?
• If you could actively shape the future, what would the future of your choice look like?
• And finally, given everything you know today, what do you believe is most likely to happen?

Working with the future

Once the future has been narrowed down to a few options, the real work can begin. Instead of trying to prepare for everything and anything that might happen, you can now work with each future separately. You can look at them one by one and ask a simple but powerful question: if this were the future we were heading into, where would it get us, and what would we do differently starting now?

This kind of thinking opens several useful paths. You can sketch a rough plan for each future, not as a commitment, but as a way to understand what it would demand from you. You can look at how plausible each option really is and decide where a bit of focused research could reduce uncertainty. Sometimes that research is small – a customer conversation, a market signal, a technical constraint – but it can be enough to rule a future in or out.

You can also decide in advance what signals you want to watch as time goes by. What would tell you that a certain future is starting to materialize? What would surprise you? That way, you’re not constantly rethinking everything from scratch; you’re paying attention to the right things.

Finally, you can make deliberate choices about risk. Some futures may be unlikely, but if they happen, everything changes. You might not prepare for them fully, but you may still choose to keep an eye on them. Others are far more likely, and those are the ones you can confidently move forward with, assuming they will happen unless proven otherwise.

This is how uncertainty becomes manageable. Not by pretending you know what will happen, but by deciding how you will respond as reality unfolds.