How to Decide When You Can't Know the Outcome

Every decision would be easy if you knew how it would turn out. Take the job that leads to fulfillment. Invest in the stock that goes up. Date the person you'll be happy with forever.

But you never know. That's not a bug in decision-making—it's the fundamental condition of it.

The question isn't how to eliminate uncertainty. It's how to make good decisions despite it.

The Illusion of Certainty

We crave certainty so much that we often pretend we have it. We research endlessly, as if enough information will reveal the "right" answer. We seek predictions from experts, as if they can see the future. We delay decisions, hoping clarity will arrive.

None of this eliminates uncertainty. It just masks it. The job might not work out. The relationship might end. The investment might tank. No amount of analysis changes that.

Accepting uncertainty isn't pessimism. It's realism. And it's strangely liberating.

Process Over Outcomes

Since you can't control outcomes, focus on what you can control: your decision process.

A good process means:

• Clearly defining what you're trying to achieve
• Generating multiple options, not just the obvious ones
• Gathering relevant information without endless research
• Weighing factors against your actual values
• Making a choice and committing to it

A good process can lead to bad outcomes. That's okay. Over many decisions, a good process wins. And even when it doesn't, you can stand behind choices made thoughtfully.

Thinking in Probabilities

Instead of asking "will this work?", ask "what's the probability this works, and what are the consequences if it doesn't?"

A 70% chance of success with manageable downside is different from a 70% chance with catastrophic downside. Both are uncertain, but they warrant different levels of caution.

Most people are either too risk-averse (they treat every risk as catastrophic) or too risk-seeking (they ignore downside entirely). Thinking in probabilities helps you calibrate.

The Reversibility Filter

Not all uncertain decisions deserve equal deliberation.

For reversible decisions, bias toward action. If you can undo it or course-correct, the cost of being wrong is low. Take the chance. Learn from the outcome.

For irreversible decisions, slow down. These warrant more research, more consultation, more sitting with the choice. The cost of being wrong is high.

Most decisions are more reversible than they feel in the moment.

Embracing Regret Minimization

Jeff Bezos asks: "When I'm 80, will I regret not trying this?"

This question cuts through a lot of noise. Short-term uncertainty feels overwhelming. Long-term regret is often about what we didn't do, not what we did.

If the worst case is survivable and the upside is meaningful, uncertainty often favors action.

After the Decision

Once you've chosen, stop second-guessing. You made the best decision you could with the information you had. New information doesn't mean the original decision was wrong—it means circumstances changed.

Learn from outcomes, but don't torture yourself over them. A bad result doesn't always mean a bad decision. Sometimes you just get unlucky.

The Deeper Acceptance

Here's the uncomfortable truth: you will make some decisions that don't work out. Some of them will be painful.

That's not failure. That's participation in life. The alternative—never deciding, never risking, never acting—is its own kind of loss.

Uncertainty isn't going away. Make friends with it.