Decision Making with Uncertainty
I remember sitting in my office years ago, running a freight brokerage that lived and died by tight timelines and tighter margins. A customer had asked us to move an over dimensional load, one of those shipments that requires a small symphony of planning.
Permits. Escorts. Insurance. Coordination across states. The shipment value exceeded $100,000s and the rate to us was around $17,000, which meant the stakes were high and the room for error was nonexistent. The schedule was already tight, which pushed us into booking a carrier we had never worked with.
On paper, everything looked clean. Their motor carrier number checked out. Their insurance was active. Their background cleared. Yet something in my gut kept tugging at me. A faint signal that something wasn’t right.
It’s a strange thing to feel responsible for someone else’s freight, someone else’s money, someone else's timeline. If I cancelled the carrier, the customer’s entire project would fall behind. They would eat the cost and probably lose faith in us. If I didn’t cancel and the carrier was shady, they could steal the freight or cause an accident. Both paths carried consequences.
As the driver got within thirty minutes of the pickup, I called my business partner in New York and told him what I was feeling. He reassured me that everything looked legitimate and reminded me we didn’t have time to recover the load if we bailed. I hung up the phone, still uneasy.
On a whim, instead of searching the carrier's name, I typed the point of contact’s name into Google. It was an unusual name and I figured maybe something would surface. The first result was a mugshot. My stomach dropped. That was all I needed.
We cancelled the pickup immediately and told the customer not to release the freight under any circumstances. The relief hit only after the dust settled. That one decision, driven by instinct and anchored by a willingness to act without perfect information, saved us from a disaster we would have worn for years.
A moment like that changes how you think about decision making. It reminds you that making quality decisions isn’t about knowing everything. Rarely do we get all the information. You learn to move anyway.
Here is how I think about decisions now, especially the ones that I feel extremely uncertain.
Define constraints
What are your non-negotiables?
What are you willing to sacrifice?
What boundary will you not cross?
What value is untouchable?
Once you clarify those constraints the field narrows. The decision gets simpler. We get in trouble when we chase options without defining guardrails. The options pull us in ten directions and we mistake motion for clarity. Good decisions come from knowing where the walls are.
Zoom out
When you face something that sits outside your purview it’s normal to feel uncertain. The problem isn’t that you lack intelligence or capability. The problem is proximity. You are zoomed so far into the idiosyncrasies of a situation that everything feels detrimental and important.
You start believing you’re not equipped to make the call. That's simply not true.
Most decisions become clearer when you zoom out. When you reference your values instead of the noise. When you anchor to the rules you don’t break and the boundaries you don’t bend. Those baseline beliefs begin to sort the chaos for you. They turn a tangled situation into something categorized and workable. We know this instinctively, yet emotions often muddy the water. Fear gets loud. Doubt pulls you inward. You forget that your values are more trustworthy than your anxieties.
Remove the emotion
It’s not that emotion is bad. It’s that emotion distorts. When you’re too close to something it becomes nearly impossible to separate the situation from the feeling around it. One question helps: if this wasn’t my situation, what would I decide? Imagine a friend handed this same problem to you and asked for advice.
Imagine you were stepping into a company on day one, asked to lead, and given a long standing rule that “we’ve always done it this way.” Would you keep it or change it? Objectivity has a way of revealing the answer you already knew but couldn’t see through the emotional fog.
Extend the time line
Decisions shrink or swell depending on the timeframe you use to judge them. Ask yourself the five year question. What will this choice create or disrupt five years from now? What will still matter, and what will fade?
When you place the problem inside a longer arc, clarity sharpens. You rise above the fog and see from a healthier altitude. Most of the choices that feel suffocating in the moment barely register on the scale of a decade. The ones that do matter rarely surprise you. They tend to align with your values anyway.
The other parties involved
Whenever other people are involved, pay attention to incentives. Ask what they stand to gain or lose. Most advice is shaped by perspective, and every perspective is shaped by position. Put yourself in their shoes. See the situation from where they sit. This isn’t about distrust. It’s about understanding the root of the advice you’re receiving. Sometimes you realize the guidance is solid. Sometimes you realize it’s rooted in their fear, not your future.
These ideas sound simple on paper, yet they become lifelines when you’re standing in the moment. When everything feels blurry. When the cost of a wrong call hangs over you. In the spaces where there isn’t enough information, yet the decision still needs to be made.
Decisions shape us long before the outcomes do. They sharpen who we are. They reveal what we stand on. They expose the hidden threads of our character. Progress doesn’t come from perfect clarity.
We grow through the questions we ask, not the certainty we wait for.
Today’s Forced Challenge: I want you to FORCE yourself to attack at least one of these challenges:
1. Map the outcomes: Take a current decision and write down the worst case, best case, and most likely scenario. Giving uncertainty boundaries makes it easier to move.
2. Argue for the option you’ve been avoiding: Pick the choice that feels uncomfortable and list three reasons it might actually be the right one. Avoidance usually hides truth.
3. Revisit a past decision: Choose a decision you regret and write what you would do differently now. Let the lesson sharpen your instincts going forward.
4. Take a controlled risk: Choose a small risk that has been sitting untouched and act on it. Reps in low stakes moments make the high stakes ones easier.
5. Close the open loop: Identify one decision that has been dragging and assign a completion date. Hold to it. Indecision weighs more than mistakes.
Every decision is a doorway. Some open gently. Some creak. Some slam behind you. Step through anyway. Trust the compass inside you. Trust the quiet clue that something is off. Trust the long arc of time. Trust that your values were built for moments like these.
Life expands for the person who chooses with courage, even when the picture is incomplete.
“In any moment of decision, the best thing you can do is the right thing; the next best thing is the wrong thing; the worst thing you can do is nothing.”
— Theodore Roosevelt