Judgement Call

Making Decisions Amid Uncertainty

The Almost Nuclear War

In 1983, a Soviet missile commander named Stanislav Petrov sat in a bunker outside Moscow, staring at a radar screen flashing with what looked like incoming U.S. nuclear missiles.

The protocol was clear: report the launch. Within minutes, global nuclear war could begin.

But something didn’t feel right. Petrov hesitated.

The system indicated five missiles had been launched while Petrov assumed a real attack would involve hundreds.

Also, no ground based radar had confirmed the attack. He trusted his judgment over the system.

He decided not to push the button.

He was right. The alert was a false alarm.

Their satellites had mistaken sunlight reflecting off clouds for missiles.

One man’s judgment call may have saved hundreds of millions of lives.

Most of us will never face choices with consequences that large.

But every entrepreneur, founder, or leader faces moments of decision where the data is unclear, time is short, and the stakes feel high.

Moments where you have to make the call without clarity or certainty.

This issue is about how to do that well: how to think, act, and choose amid uncertainty.

How To Make Better Decisions

The following is a simple framework to help you make better decisions. Subscribers can find a link on the resources page with this framework applied to dozens of common business decisions.

Problem Identification

“If I had an hour to solve a problem, I’d spend 55 minutes thinking about the problem and 5 minutes thinking about solutions.”

Albert Einstein

Bad decisions often begin as poorly defined problems. Petrov’s problem wasn’t understanding protocol or computer system malfunctions, it was avoiding a global catastrophe.

In business, we’re rewarded for speed and action, so we tend to jump straight into fixing instead of framing.

We’re all eternally grateful Petrov framed correctly.

Typically, we chase symptoms: slowing sales, rising churn, missed deadlines.

But until you clarify the root problem, solutions can be mere bandaids on festering wounds.

The first step in any sound decision isn’t to choose but to define.

What exactly are you solving for? What’s the real issue beneath the surface one?

A few prompts that help:

  • Why is this a problem? (Use the Five Why’s Framework)

  • What assumptions am I making about why this problem exists?

  • Who else sees the problem differently and what might they be right about?

Good decisions start with a clean frame. Can you describe the problem clearly in one sentence and without jargon?

If so, you’re ready to think about solutions.

Knowns vs Unknowns

Petrov knew the system had indicated five missiles had been launched. He also knew that ground radar had not confirmed. Two valuable pieces of information that supported a false alarm.

Once you’ve defined your business problem, anchor yourself in reality: What do you actually know?

Not guesses, not assumptions but facts you can defend. These are your fixed points.

Then map the other side of the ledger: What remains unclear or unknowable right now?

Petrov didn’t know why the system had sent the missile launch warning. Malfunction or was the this just the beginning of a larger launch sequence?

Unknowns are the variables, assumptions, and blind spots that create uncertainty.

You don’t need perfect information to move forward.

You just need to see the boundaries:

  • Knowns frame reality.

  • Unknowns show you where risk and opportunity live.

When you can name both, the fog lifts.

Choices become clearer, and you can better decide what trade-offs to make.

Timeframes

Every decision has two clocks:

when you need to make the call, and when you’ll know if it was the right one.

Petrov had very short clocks on both accounts. He had to decide within minutes and would know the quality of his decision shortly after.

For your own decisions, start by asking:

When does this decision actually need to be made?

Most choices feel urgent because we want to get past them, not because they’re time-sensitive.

Clarifying the real deadline often reduces pressure and prevents rushed judgment.

Then look ahead:

How long until I get feedback?

Some decisions reveal their quality within hours or days.

Others take weeks or months.

Knowing the feedback loop helps you size the decision. Fast feedback usually means low risk and high reversibility; slow feedback means the opposite.

When you pair the decision deadline with the feedback timeline, you see the decision as much of a timing problem as an information one.

And with the clock visible, the next move becomes clearer.

Reversibility

Not all decisions deserve the same level of scrutiny.

For Petrov, his decision was almost irreversible. Had he notified his command they would have certainly counter-attacked. Incorrectly delaying the decision would have provided the US a decisive advantage.

Like Petrov’s, some decisions are one-way doors. Once you walk through, you can’t easily go back.

Others are two-way doors that allow you to step through, get feedback, and reverse course if needed.

Most leaders treat every decision like a one-way door.

That’s why they feel heavy. That’s why they drag out.

But in reality, most decisions are reversible, especially in business.

Before agonizing over the “perfect” choice, ask a simple question:

How hard is this to unwind?

If it’s a two-way door:

  • You can test, learn, and adjust.

  • The cost of being wrong is low.

  • Speed matters more than precision.

If it’s a one-way door:

  • You need to slow down.

  • Gather more information.

  • Get outside perspective.

  • Be clear on risks, commitments, and downstream impact.

Reversibility reframes decision-making from “What if this is wrong?” to “What happens if I need to change my mind?”

It shifts you from fear-driven choices to learning-driven action.

When you identify a decision as reversible, it creates room to move faster.

When you identify one as irreversible, it gives you permission to take your time.

This lens alone can eliminate half the stress you feel around decision-making.

The Downside

Every meaningful decision carries risk. For Petrov, global annihilation was the ultimate downside outcome.

Risk can never be eliminated but it can be better understood.

When you’re facing uncertainty, the most important question you can ask is:

What is the actual downside if I’m wrong?

Not the imagined downside.

Not the story your anxiety tells you.

The real, concrete, measurable downside.

Map it out clearly:

  • What’s the worst realistic outcome — not the worst imaginable one?

  • How expensive is a mistake — in time, money, trust, or opportunity cost?

  • Can I absorb the downside without harming the business?

  • What safeguards or constraints can I create to limit the damage?

When founders skip this step, two things happen:

They overreact to small risks and under-react to large ones.

But once you quantify the downside, clarity improves instantly.

Most “big” decisions turn out to be small. The cost of being wrong is low.

And some decisions that feel routine reveal hidden, meaningful risk.

Understanding the downside helps align your effort with reality.

It shows you whether you should move fast, move carefully, or not move at all.

Good judgment often comes down to knowing which risks are worth taking and which ones can quietly sink you.

The Next Step

Petrov had to make a quick decision with limited information while the fate of the world hung in the balance.

Whether you should quit your job to make the leap, hire a new employee or green light a major project doesn’t carry the same stress or gravity but good decision making applies all the same.

Your framework is simple:

Define the real problem.

Know what’s true.

Name what isn’t.

Check if the decision is reversible.

Understand the downside.

Clarify the timeframes.

Use it on one decision you’re facing right now.

You’ll move with more confidence, less noise, and clearer judgment even amidst uncertainty.

Good calls aren’t about predicting the future.

They’re about thinking well in the present.

My goal with The Leap is to provide you each Saturday with the knowledge, tools and lessons learned to help you get started and keep going toward building your future. 

Whether you are making the leap to startups, solo-entrepreneurship, freelancing, side hustles or other creative ventures, the tools and strategies to succeed in each are similar.