Welcoming Fear, Finding Real Leadership

Discovering Real Leadership on the Edge of a Cliff – with Brett Kistler

What can extreme sports teach leaders about fear, shame and truly honest decision-making in business? In this conversation, entrepreneur, executive coach and former world‑traveling wingsuit pilot Brett Kistler shares how thousands of jumps off planes and cliffs have rewired the way he relates to risk, responsibility and human connection – and why that matters for anyone leading a team today.

Brett spent over a decade living nomadically while building a remote software company, skydiving, BASE jumping and wingsuit flying around the world. What started as curiosity and “a form of self‑discovery” became a radical training ground in presence, emotional awareness and the courage to listen to fear rather than conquer it.

“Ultimately, the core of it is that it was a form of self‑discovery for myself.”

Early in his career as a jumper, Brett bought into the typical “no fear” mindset. Fear was an enemy to be pushed through, a test of courage and ego. Over time, as he watched who actually survived in the sport, that story fell apart. The people with long, injury‑free careers were not the bravest in the conventional sense – they were the ones most honest about their fear.

“I noticed that it was the people who had the longest careers with the fewest injuries [who] had a different relationship with their fear… they would welcome the fear, they would be wearing their fear on their sleeve.”

On exposed exit points – cliffs, buildings, bridges – the most seasoned jumpers were often the first to say “I’m scared, I’m scared shitless” out loud. They did not let fear run the show, but they also did not suppress it to look strong. Instead, they acknowledged it, shared it with the group, and then took the time to regulate and feel what was underneath: the grief of walking down from a jump, the social fear of disappointing friends, the doubt about their own skills that day.

This is where Brett draws a direct line to executive life. In a wingsuit, there is no time for endless pros and cons lists; action emerges from a fully felt, fully processed emotional landscape. In leadership, however, people often spin on decisions for weeks or months, believing they are “thinking it through”, when in fact they are circling around an unfelt feeling.

“If you think that you have a decision to make… it’s simply because there’s an emotion that you haven’t felt.”

That emotion might be the grief of a potential failure, the shame of a past mistake, or the fear of being seen as the “bad leader” who has to cut staff to save the company. When those feelings are off‑limits, decisions become cloudy and reactive. Leaders find themselves making choices to avoid feeling something rather than to optimise for the real outcome.

Shame, Brett says, is especially corrosive. It “stagnates an emotional experience” – whether on the edge of a cliff or in a boardroom. A leader who is worried about losing face in front of the team will unconsciously block fear, sadness or anger, and will then make decisions driven by self‑protection instead of connection.

“My decisions are going to be clouded, because I’m really making decisions to avoid feeling something rather than to optimize for the outcome.”

Over years of jumping and building companies, Brett has come to see both business and extreme sports as profound personal growth paths. For a scaling founder or executive, every crisis is a pressure cooker that forces them to question “load‑bearing assumptions” about who they are and what they are here for. Growth is less about becoming a bigger, more heroic leader and more about emptying out rigid identities so that something larger – a clearer culture, a shared set of principles, a more honest team – can move through.

He now works closely with coach Joe Hudson and co‑hosts the Art of Accomplishment podcast, supporting leaders to adopt what they call the VIEW mindset: Vulnerability, Impartiality, Empathy and Wonder. In practice, that looks like saying the scary true thing in a meeting, staying oriented to process rather than outcome, being fully with another’s emotional experience while staying in one’s own, and lingering in powerful questions without rushing to answers.

“What is the scary thing for me to say right now?”

Brett and his teams have even institutionalised this. In meetings, they run a round where everyone shares “the scary thing that hasn’t been said yet”. In coaching, he uses a simple internal signal – the moment his “sphincter puckers a little bit” – as a cue that he has just found the question that most needs to be asked. Speaking to the “elephant in the room” may make people angry or uncomfortable, but it can also be a huge relief and a gateway to real connection and clarity.

The conversation then turns to AI, identity and the future of work. As software, coaching and content all get reshaped by intelligent tools, many people will have to reinvent who they are beyond their economic output. Brett believes this disruption can become a profound invitation if we allow it to strip away outdated measures of worth and force us to ask deeper questions about what really matters.

When Vesna asks what he thinks the world needs most right now, Brett refuses to offer a grand, abstract answer. Instead, he describes a kind of humble listening – starting with his own life, his own unmet needs, and trusting that what is true there will resonate with others when he dares to create it in the world. Community, recognition and a deeper sense of belonging keep surfacing in his own experience, and he takes that as a signal of what many others are craving too.

“It feels like hubris to have any opinion on what I think the world needs more. I’d rather listen… what do I need right now?”

At the same time, he is clear about the kind of future he wants to help build: one where human worth is no longer tied almost exclusively to GDP and economic output, and where technology – including AI – is used to reclaim, not erode, our capacity for presence, care and connection.

“I would love to see a future where our worth in society is decoupled from economic output and includes more of our humanity.”

He imagines AI freeing more people from purely transactional work so they can show up as humans for one another – creating, listening, grieving and dreaming together. In that sense, healing innovation, emotional honesty and courageous community‑building are not luxuries, but essential skills for navigating what comes next.

If the talk resonates with you, we’d recommend you listen to these episodes too:

• Seth Godin – Dancing with Fear 
• Bob Chapman – Truly Human Leadership  
• Stefan Beiten – Bringing Trust and Purpose to the World