Strategic Living

Decision Making Under Uncertainty

Most major decisions are not easy to make. Oftentimes, the information you need doesn’t exist yet, only revealed in hindsight after the fact. Yet you still have to choose now, not later. You want clarity before acting, but clarity only comes from action. You want certainty before committing, but commitment is what generates outcomes to be certain about. The fog only lifts after the decision is made.

As a result, there will never be a way to eliminate uncertainty. But there are ways to decide and act despite it.

Absent Clarity

There’s a myth that good decisions come from complete information. That if you just research enough, analyze thoroughly enough, wait long enough, the right choice will become obvious. But most consequential decisions involve variables you can’t measure, outcomes you can’t predict, and information that only exists in the future. You’re choosing between options without knowing which will suit you, what unexpected consequences they will have, or how much risk is truly involved. The stakes are real but unclear. The consequences appear in ways you can’t predict.

Besides, perfect information wouldn’t even solve the problem. Even if you somehow knew every outcome, you still wouldn’t know which outcome you’d prefer until you experienced it. Your future self, shaped by the very decision you’re making, will have different values, different priorities, and different tolerances for what matters to you now.

Because we have free will, uncertainty is part of how the world works. The clarity you’re waiting for isn’t coming.

Strategies

When facing uncertainty, people reach for strategies, such as:

Gather more information. But research has diminishing returns. Past a certain point, you begin collecting information for its own sake instead of using it to help you make the decision. Beyond that, you’re mostly finding contradictory opinions and reasons to second guess yourself. Information gathering becomes procrastination disguised as diligence.

Trust your gut. But intuition is pattern recognition and pattern misrecognition. Your gut might be detecting genuine warning signs, or it might just be conflating novelty with danger, or familiarity with safety. Gut feelings alone are not reliable enough to follow blindly.

Imagine future regret. But people are terrible at predicting what they’ll regret. Things that seem catastrophic now often become “thank God that didn’t work out” stories. Choices that felt safe can calcify into years of dissatisfaction you didn’t see coming. The brain rationalizes the circumstances it is given, making it impossible to accurately predict how you will feel after any decision. You’re guessing what a different version of you will feel.

Run experiments. But not all decisions are capable of being tested. And even when experiments are possible, they’re imperfect. The novelty of a trial run doesn’t predict the reality of sustained commitment. You can’t fully feel the affects of a choice unless you actually go through with it.

Make it reversible. But treating everything as reversible prevents you from committing. Some opportunities only reveal their value when you commit beyond the point of easy exit. And even “reversible” choices have hidden costs that accumulate. Besides, some choices can’t be made reversible without significant consequence, making them impractical.

None of these strategies solve the problem because the problem isn’t solvable.

Authenticity

The “solution” is not to look for the “right” way to decide under uncertainty. Rather, look for your way to navigate under uncertainty.

Know Your Tolerances

Different people can tolerate different kinds of uncertainty. Some are fine with financial risk but terrified of social rejection. Others can handle relational ambiguity but need career stability.

The question isn’t “Is this risky?” but “Is this a risk I can live with?” Knowing what kinds of uncertainty you can and can’t handle lets you filter decisions honestly. You’re not asking “What should I do?” You’re asking “Given what I know about myself, what makes sense for me?”

This means accepting that your tolerances shape your trajectory. If you can’t tolerate financial insecurity, you’ll build a different life than someone who can’t tolerate creative constraint. Neither is wrong. But misconstruing what your tolerances are leads to choices that aren’t made with you in mind.

With that being said, you will still occasionally be wrong. The self cannot be defined in any permanent way, and destiny has a funny way of proving your strongest assumptions inaccurate.

Commit to Learning

Most decisions are framed as success/failure binaries. Either it works out or it doesn’t.

But the outcome isn’t the only thing you’re getting. You’re also getting information, experience, relationships, and clarity about what you actually want versus what you thought you wanted. Not to mention the literal uncertainty about what this decision could bring.

A “failed” relationship may have taught you how to better approach the next one. A job that didn’t work out may have clarified what kind of work you find meaningful. Reframing decisions as learning opportunities rather than fuckups reduces the stakes. You’re taking a step, seeing what happens, and adapting.

This doesn’t justify being reckless. It means recognizing that even “wrong” choices move you closer to clarity if you’re paying attention.

Leap of Faith

“How do I know I’m ready?” You won’t. It’s a leap of faith.

Corny pop culture references aside, action is what generates confidence. Commitment is what generates clarity. You don’t wait until you’re ready, you become ready by starting.

This means acting while still uncertain. Making the choice even though you’re not sure it’s right. Stepping forward while the fog is still thick, trusting that you’ll figure it out as you go.

The only alternative is waiting until you feel ready, which often means waiting forever. Readiness is a feeling, and feelings are inconsistent and unreliable. Most of the time, “ready” looks like: “I’ve thought about this enough, and now I’m choosing to act despite not knowing how it’ll turn out.”

To be fair, this is easier said than done. But at a certain point, you just gotta say “fuck it” and do something. At a certain point, the chance that the decision would become clear if you just waited a little longer is an excuse to justify procrastination.

Trust Your Process

You can’t control the outcomes. But you can control how you make decisions.

If your process is sound: honest about your tolerances, thoughtful about the sacrifices, and willing to learn from the results, then you can trust your decisions even when they don’t work out the way you hoped.

Because when a decision doesn’t pan out, you’re not asking “Did I make the right choice?” Rather, you’re asking “Did I make the choice in the right way?” Did you think it through? Did you acknowledge what you didn’t know? Did you act from your values rather than fear?

If yes, then the decision was sound even if the outcome wasn’t what you expected or wanted. You did what you could with what you had. That’s all anyone can do.

Doubt

The hardest part isn’t making the decision. It’s living with it afterward when doubt creeps back in, when things don’t go as planned, when you wonder if another path would have been better.

But there’s no way to know. The life you didn’t choose exists only in imagination, and imagination is as unreliable as the emotions it feeds off of. It shows you exaggerated versions of the unchosen path while showing you every flaw of the path you’re currently on, flaws you would have never known about if you didn’t choose this path. In the same way, you can’t be aware of the flaws in a path you didn’t choose.

You can’t optimize your way out of this. Uncertainty doesn’t even end once you choose, it just moves on to something else. Before the decision, you’re uncertain about what to do. After, you’re uncertain about whether you did the right thing.

The only way forward is to think, decide, commit, and then adapt as new information emerges. Not because you’re sure you’re right, but because standing still isn’t an option and waiting for certainty is a fantasy.

You made a choice with the information you had, the values you held, and the person you were at the time. Now you see what happens, learn what you can, and adapt if necessary.

The fog of the future will remain regardless. But you can learn to navigate it anyway.