Endurance, Uncertainty, and Leading When the Path Disappears: A Conversation with Stephanie Case

If today’s leaders feel like the ground is constantly shifting beneath them, they’re not wrong. Organizations are navigating uncertainty on multiple fronts at once: economic pressure, burnout, global instability, talent retention, and the ongoing demand to do more with less. The playbooks that once worked no longer apply cleanly, and pushing harder isn’t delivering better results.

That’s why Stephanie Case’s work resonates so strongly with audiences right now.

An elite ultrarunner, humanitarian, and founder of Free to Run, Stephanie has built her life and career in environments where certainty doesn’t exist. From 450km non-stop races to conflict zones in Afghanistan and Gaza. Her keynotes don’t rely on abstract motivation or buzzwords. Instead, they offer leaders something far more useful: a grounded framework for adaptability, resilience, and sustainable performance when conditions are unpredictable and the margin for error is slim.

We sat down with Stephanie to explore the endurance mindset, redefining failure, navigating uncertainty, inclusion through action, and how leaders can pace their organizations for longevity, without the burnout.

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TL;DR

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Q&A with Stephanie Case

The “Endurance Mindset” in the Boardroom

You’ve navigated some of the most high-pressure environments on Earth, from the mountains of the Italian Alps to conflict zones in Afghanistan and Gaza. In your keynotes, you often speak about the “Endurance Mindset.” How can organizational leaders apply the gritty, mile-by-mile adaptability of an ultramarathon to the rapid disruptions they face in the business world today?

In an ultramarathon, the plan you start with rarely survives the first 50 kilometers. Anything can happen when you’re out on the trail: the weather can change in a minute, the terrain can give way, or your body can fail. I once partly lost my vision during a race and had to figure out how to adapt my stride when I couldn’t see the rocks or tree roots underfoot – and yet, I still finished on the podium.

When life throws you a curveball, success depends on your ability to pivot without panicking. In volatile environments – whether on a mountainside or in a conflict zone – the strongest performers aren’t the ones who cling rigidly to a plan. They are the ones who can ask “what’s the best next step right now?” True leadership comes from knowing when you need to change course in order to stay on track. That’s the endurance mindset that I talk about with leaders.

For organizations facing rapid disruption, this means adjusting goals in real-time without losing sight of the bigger purpose, training people to make decisions based on imperfect information, and building trust within teams so that people raise problems early, rather than hide them until it’s too late.

Endurance isn’t about pushing harder or working longer hours. It’s about staying responsive and adaptable long enough to finish well.

For leaders navigating rapid change, uncertainty, and high-stakes decision-making, Stephanie’s perspective offers a grounded and highly relevantleadership lens.

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Redefining Failure as a Strategy

Many of us are conditioned to view failure as a dead end, yet you advocate for “choosing failure” as a path to growth; deliberately signing up for challenges you aren’t sure you can finish. Can you share a moment where a “failure” in your running or humanitarian work provided a blueprint for success that you now share with corporate teams?

Some of the most valuable lessons in my life came from races — and missions — I didn’t “win.”

I deliberately sign up for races where the outcome is uncertain, or sometimes, when failure is almost guaranteed. Why? Because if you only pursue goals you’re confident you can achieve, you’re not innovating — you’re rehearsing something you’ve already mastered.

One example I often share with corporate teams is a race I entered called the Barkley Marathons, which at that time no woman in its decades-long history had ever finished. My chances of succeeding were almost zero – and indeed, despite two attempts, I failed at both.

But it taught me so much more about how my body and mind worked under stress, and I’m convinced the experience was pivotal in helping me succeed at a much harder race I entered two years later.

Choosing failure strategically means experimenting, opening yourself up to vulnerability, and treating setbacks as intelligence, not embarrassment. Failure isn’t the opposite of success. It’s often the instruction manual for how you get there.

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Navigating the Unpredictable: Off Course

Your new film, “Off Course,” which recently screened at the Banff Centre Mountain Film Festival, takes a deeply personal look at the intersection of elite performance and the unpredictable journey of motherhood and fertility. What parallels did you discover between the resilience required for this personal journey and the resilience required to lead through professional uncertainty?

Trying to become a mother after multiple pregnancy losses and failed rounds of IVF was profoundly destabilizing. It dismantled many of the assumptions I had built my life around – especially the belief that effort reliably leads to outcome. In ultrarunning, patience and persistence usually move you forward. In trying to become a parent, none of that logic seemed to apply. I could do everything “right” and still end up exactly where I started – or further back.

That loss of cause and effect is what makes uncertainty so difficult, whether personal or professional. When outcomes feel uncontrollable, our instinct is to become defensive: to minimize risk, narrow our vision, and focus on everything that could go wrong. In leadership, this often shows up as hesitation, over-control, or a retreat into the familiar. It feels safe – but it also limits what’s possible.

When dealing with uncertainty, instead of focusing on everything that could go wrong, I learned the importance of asking what if everything goes right? Choosing to believe that I could indeed have success helped to give me the energy and confidence to keep trying.

Resilience isn’t about blind optimism. It’s the capacity to stay open and forward-looking even when you don’t control the outcome. Resilience is choosing how you respond to setbacks, and deciding to move ahead with courage, curiosity and purpose.

A link to the trailer of the film can be found on my website here.

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The Intersection of Sport and Human Rights

You founded Free to Run to empower women and girls in conflict regions through adventure sports. For organizations looking to build more inclusive and purpose-driven cultures, what does your work with Free to Run teach us about the power of “reclaiming space” and challenging the status quo?

At Free to Run, “reclaiming space” is both literal and symbolic. In many of the places in which we work, women and girls have been told – explicitly or implicitly – that public space, movement and ambition are not for them. When they run together, visibly, through streets or on trails where they were never meant to be seen, they aren’t just exercising. They are challenging a system that was built without them in mind.

The same dynamic exists inside organizations and businesses. Who appears in imagery, whose voices are amplified in meetings, and who is trusted with authority are not neutral choices. They quietly signal who belongs and should shrink. These signals shape behaviour long before any formal policy does.

What our work shows is that culture doesn’t shift because people are told to be confident or inclusive. It shifts when people are given real permission to take up space, and when the cost of doing so is lowered. Change happens not when the system invites people in, but when it stops asking them to justify their presence in the first place.

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Sustainable Success vs. Burnout

In a culture that often glorifies “the hustle,” you emphasize that peak performance comes from balancing ambition with recovery. Drawing from your experience running 450km non-stop races, what is one counter-intuitive piece of advice you give to executives who are trying to pace their organizations for longevity rather than short-term wins?

The most counter-intuitive piece of advice I give to leaders is this: slow down on purpose, before you’re forced to.

In ultramarathons, the biggest mistakes aren’t made by people who are under-prepared – they’re made by people who feel strong early and decide to push too much, too soon. They skip rest, ignore the warning signs, and treat recovery as a reward rather than a requirement. Almost without exception, those are the runners who unravel later. Admittedly, I don’t always take my own advice. I have to repeatedly remind myself of this lesson, particularly when I feel like I’m on top of my game and the drive to push forward is fierce!

Organizations and businesses behave the same way. When momentum is high, leaders double down instead of creating space. But sustainable performance doesn’t come from constant intensity—it comes from knowing when to push and when to pull back. Periods of focus have to be deliberately paired with periods of recovery, reflection, and recalibration.

Longevity isn’t about lowering ambition. It’s about resisting the urge to spend all your energy at once. The goal isn’t to see how much your organization can endure—it’s to design a pace it can sustain.

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Award-Winning Advocacy

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Finding Opportunity Inside Constraints

You once trained for an ultramarathon by running circles inside a secure compound in Kabul. When you are speaking to audiences who feel constrained by their current resources or environment, what is the core message you want them to take away about finding opportunity in the most restrictive of circumstances?

Perspective is everything.

When I was living in Afghanistan, I trained for an ultramarathon by running endless loops inside a secure compound. At the time, it felt deeply restrictive. I compared it to the freedom I’d known running outside in my home country — open trails, open roads, open skies — and all I could see was what I had lost.

Then I moved to Gaza.

There, I didn’t even have access to a compound. All I could do was run up and down the stairwell of my apartment building and make tiny loops on the roof. That’s when something shifted. Suddenly, the Afghan compound felt enormous. Spacious, even. I realized I hadn’t been constrained by the environment as much as I’d been constrained by my point of reference.

That experience fundamentally changed how I think about limitations.

Constraints don’t exist in isolation; they exist in comparison. When we fixate on what we used to have or what others seem to have, even workable conditions can feel unbearable. But when we adjust our perspective, the same environment can reveal unexpected room to move. This is the message I share with teams who feel boxed in by tightened budgets, heightened bureaucracy, or limited resources: progress doesn’t start with better conditions; it starts with reframing the conditions you’re already in.

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Looking Ahead

Between your humanitarian work, your film, and your racing, you are constantly redefining limits. What is the next “impossible” challenge you are tackling, and how can organizations partner with you to bring that energy of reinvention to their next event?

I have some exciting personal goals this year that I’m tackling. Becoming a professional athlete as a new mom at the age of 43 is exciting, but also brings about some interesting challenges! I want to prove to myself and to other women that you can keep striving for big things at this stage of life. Along with some ultramarathons in Asia and Europe, I have an adventure planned in a rather extreme environment later this year, where I hope to break a world record that has not yet been attempted by a woman – stay tuned! I am also starting to write a book about my experiences working on the frontlines of humanitarian emergencies and running ultramarathons in between. It is a memoir about ambition, uncertainty, and redefining strength when nothing goes according to script.

Stephanie’s story strongly resonates with organizations focused on advancing women in leadership and business, particularly in conversations around ambition, identity, and sustainability over the long term.

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The Time to Try

We often let logic stifle our biggest dreams, yet Stephanie Case proves that the “impossible” is merely a starting point. By sharing her experiences training for ultramarathons in active conflict zones, she demonstrates how embracing a little “crazy” can radically redefine your life and potential.

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Why Event Planners Hire Stephanie Case

When organizations are facing uncertainty, burnout, or the pressure to perform without clear answers, Stephanie Case delivers something rare: a message that doesn’t simplify complexity. Instead, it helps leaders navigate with confidence and determination. 

Her keynote connects endurance sport, humanitarian leadership, and real-world organizational challenges in a way that is honest, practical, and deeply motivating. Audiences leave with a clear understanding of how to adapt, how to pace themselves and their teams, and how to lead with courage when outcomes aren’t guaranteed.

For conferences focused on leadership, resilience, inclusion, sustainability, or navigating change, Stephanie Case is a powerful keynote choice.

Hire Stephanie Case as a keynote speaker for your next conference, summit, or leadership retreat. Contact an agent today.

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FAQs – Endurance & Leadership at Work With Stephanie Case

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Keep up with Stephanie Case

Website: stephaniecase.com

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