How founders can learn to navigate uncertainty

Last year, I attended the Polyopportunity event by House of Beautiful Business & the Acosta Institute in NYC. I had the honor of sitting next to Maggie Jackson. She is a journalist, thinker, and author of several books, most recently Uncertain: The Wisdom and Wonder of Being Unsure.

After some deep conversations about our shared interest in cognitive psychology, I asked her if she’d be open to an interview for the Deep Dive. She said yes. What follows is a conversation that changed how I think about the discomfort in unknown situations & decision-making in times of uncertainty.

This Deep Dive is about one idea: Uncertainty isn’t something to fear, it’s something to lean into.

Ready? Let’s dive into: The Art of Being Skillfully Unsure – and How Founders Can Learn to Navigate Uncertainty.

STARTING POINT: UNCERTAINTY ISN'T WEAKNESS – IT'S POSSIBILITY

Before you start, take a moment to pause.
Think about the word uncertainty.
What emotions or thoughts come up?
​ Take 2 minutes to listen in.

If you’re like me, or like most founders, it’s probably not a warm and fuzzy feeling. In the business world uncertainty tends to be seen as something bad, something we need to eliminate.
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But in writing her book, Maggie discovered the powerful role that uncertainty plays in adaptability, resilience, and innovation. So, she starts by explaining to me, that there are two types of uncertainty:

• Aleatory Uncertainty​
The general unpredictability of life. Things we can’t fully control.
E.g., market shifts, sudden user behavior changes, global events.

• Epistemic Uncertainty​
Our internal response to the unknown. The recognition that we have reached the limits of our knowledge.

“Discomfiting as it is, uncertainty is a space of possibilities.”

In business, epistemic uncertainty is often misunderstood as indecisiveness–it’s seen as weakness. We've developed, as Maggie puts it, “an allergy to uncertainty.” So, she tells me how we should understand uncertainty instead:

“Uncertainty is the lynchpin to thriving in new, ambiguous, or unexpected situations. It is the foundation of our ability to flourish in times of flux."

She asserts that uncertainty is not an end goal, but that being uncertain skillfully is a very important cognitive skill set founders should establish, because it is highly related to:

• curiosity

• open-mindedness

• creativity

• resilience

WHAT HAPPENS IN YOUR BRAIN WHEN YOU'RE UNCERTAIN

Since I’ve connected with Maggie on this topic, and it covers a good part of her book, of course I want to know more about: How does uncertainty show up in our minds and bodies, and how is it connected to curiosity?

The first thing she emphasizes is: Everyone feels uncomfortable when they are unsure. That’s natural, because humans evolved to need answers. But in times of change, learning how to be productively unsure separates success from failure.

“Scientists call uncertainty a state of arousal. It indicates that you are on your toes. It is a form of good stress.”

Maggie breaks it down:

When you are uncertain:

• Focus sharpens

• Working memory increases

• Attention heightens

• The brain becomes more receptive to new information

“The discomfort is actually something to lean into, or at the very least, accept. In routine situations, you can operate on autopilot. But when things are unpredictable and new–that's when you really want to harness the power of uncertainty.”

According to her research, this state is nothing to fight, it’s actually a high-performance condition.

SURVIVAL VS. PERFORMANCE MODE

If there’s one group of professionals constantly facing uncertainty–it’s those who are trying to build something new, who are looking for product-market fit, and who are constantly risking their financial stability. So, I tell her about the Startup Snapshot Report on mental health and that 72% of founders admitted to facing some form of mental health issue during their journey–ranging from anxiety to burnout.

I want to know: How are these mental health issues connected to uncertainty?

“Anxiety is by definition a fear of the unknown. When you're afraid of something, you experience a different stress response than when you are leaning into the “arousal” of uncertainty. When you are afraid, you're going into survival mode, not performance mode.”

“It’s important to lean into the arousal of uncertainty and avoid the trap of fear. Because we all know we can't think in higher-order ways when we're afraid. If you are in a state of arousal–good stress, uncertainty mode, performance mode–you’re open to what's going on. You are leaving behind the fear that clouds your vision."

Here is an overview of what your reaction to uncertainty can look like in these two different modes:

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“Scientists are beginning to discover that uncertainty is highly related to resilience. They are actively treating anxiety by helping people increase their tolerance of uncertainty. And they found that leaders who are tolerant of uncertainty are more likely to direct teams that produce breakthrough innovations. That means: Uncertainty is good stress. It is distinct from fear–this needs to become our starting point.”

HOW TO MAKE BETTER DECISIONS IN THE UNKNOWN

Being faced with constant uncertainty brings a very specific challenge with it. How do you make good decisions as a founder when the solution is never visible or known from the start? How should uncertainty be integrated into the decision-making process?

“So just consider for a moment that our first thoughts are almost invariably based on what we already know. Scientists call this predictive processing. The brain is constantly expecting and assuming that what was before has remained so. You know the way to work. Your office hasn't moved since you got there yesterday. We expect that the people we work with will be generally the same as they were the day before.”

And for her, it's clear: In new situations, this way of “resting on old knowledge” is not going to help you. So what is?

"Adaptive expertise, the ability to move past old, insufficient assumptions and instead calibrate our understanding to the demands of a new, murky problem."

How to become an adaptive expert, according to Maggie’s research:

❓Inhabit the question

Take time to fully diagnose the problem or situation. Dive deep into the question: What is going on here? What’s gone wrong?

💡 Widen the frame of your understanding

Look at the situation from different angles. Consider multiple elements and perspectives of different people to understand the problem thoroughly.

🧠 Deepen your understanding

Use experiments or gather evidence to test and evaluate the best theory to fit this new situation.

“Uncertainty does slow you down. Let’s be honest about that. But in times of change, wielding uncertainty is crucial. Only by being skillfully unsure can you find the better answer.”

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"Uncertainty, that's when you care."

– quote from a surgeon Maggie interviewed in her book

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WHAT CAN YOU DO TO TRAIN UNCERTAINTY

If you’re like me, and you just realized that you need to change something about your perspective on uncertainty, then let’s get to the practical part. Here’s what Maggie recommends to build uncertainty tolerance:

• Reframe the discomfort of uncertainty as good stress
• Practice wielding uncertainty by taking on a bit of the unknown each day
• Be meta-aware, zoom out, and take time to reflect

Uncertainty Tolerance Toolbox

1. Boosting Tolerance of Uncertainty

​Scientists are treating anxiety with a form of uncertainty-exposure training. You can try this for yourself:
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Commit to 12 weeks.
Each day, do one thing that makes you feel slightly unsure.

• Say no even though it’s hard
• Talk about a new project before it’s ready
• Ask the hard question in the room​

Find new situations every day that feel like a stretch for you.

“By exposing yourself to uncertainty each day, you are gaining skill and practice in being productively unsure. You're learning that the experience of the unknown is not necessarily a disaster.”

2. Leaning into Uncertainty in Crunch Times

We fixate too much on outcomes: KPIs, metrics, decisions. This fixation closes the gap that is meant for creativity.

“We too often rush to close down the space between question and answer–and yet that is where we expand our possibilities.”

Instead of leaping to conclusions, the next time you’re in a new, unknown situation, try this:

→ Pause & breathe
→ Tune into the emotions that arise in your body
→ Remind yourself: The stress you’re feeling is good stress​
→ Follow the steps of adaptive expertise

"Tuning into the arousal of uncertainty is a kind of wakefulness, you’re in the present moment. Of course, we need goals–especially founders–but overly fixating on outcome lowers performance. By loosening our focus on outcome and instead leaning into uncertainty, we become highly attuned to the demands and nuances of the moment.”

3. Cue Words

You can help yourself lean into uncertainty in crunch times by developing a specific word or phrase that you use to pivot your focus back to the present, uncertain moment. Maggie mentions that athletes do this too, to re-center themselves under pressure.

Examples:
→ “Focus.”
→ “Game on.”
→ “Stay present.”

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Personal share:

I’ve noticed that I’m likely to hold my breath in high-stress, novel situations. So, I’ve also trained myself to use a cue word. For me, this one is: Breathe.

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What feels natural to you?

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FINAL INSIGHTS: MAGGIE'S OWN SHIFT

A final question I wanted to ask Maggie was whether writing her book changed her perspective on uncertainty.

And I loved the moment: She laughed and said, “Yes–completely.”

Initially, she set out to write a book on thinking well in the digital age, convinced that uncertainty was a state of mind that needed to be eliminated in order to problem-solve or innovate.

But then she discovered that many scientists in disciplines such as neuroscience, anthropology, management, organizational psychology, among others, had begun to overturn our old ideas of uncertainty as weakness and inertia.

She realized that her book should explore uncertainty’s wisdom.

“I always thought of myself as someone who liked to reflect, look at different sides of a question. And I was often criticized because I didn’t have instant, sure opinions. But I’ve learned that the idea of being thoughtfully unsure is nothing to be ashamed of. I’ve seen it in my own writing process. There is no recipe that tells you exactly what to do to write a book. So, I learned that my frustration is natural and that if I am uncertain, that means I am thinking well.”

And her final words in my interview are—I believe—also the perfect ending to this Deep Dive:

Uncertainty is wisdom in motion.