Risky Routes

Most people experience history through headlines. Christian Caryl experienced it firsthand.

When Christian arrived in Iraq in August 2003, the war was technically over. The future was not.

The country was in a strange in-between state. The old regime had collapsed, the new Iraq had not yet emerged, and nobody—from military leaders to journalists to ordinary Iraqis—could confidently explain what would happen next.

In this episode of Risky Routes, Christian reflects on reporting from Iraq during one of the most consequential geopolitical moments of the 21st century. We talk about the gap between perception and reality, the absurdity and uncertainty of the early occupation, and what daily life actually looked like beyond the headlines.

More than two decades later, Christian returned to Baghdad and found a city that was dramatically different from the one he first encountered. The contrast became an opportunity to reflect on how countries, conflicts, and people evolve in ways that outsiders often miss.

Along the way, we discuss the lessons journalism teaches about leadership and decision-making: trust your instincts, seek firsthand experience, question conventional wisdom, and pay attention to the stories nobody else is telling.

This episode is about uncertainty, curiosity, and the value of getting close enough to the world to see it for yourself.

The most dangerous part of Tatiana Fofonova's trek through Nepal wasn't the mountain.

Before setting off on a year of solo travel, Tatiana (CEO and Cofounder of Koda Health) spent months preparing herself physically and mentally for the adventure ahead. After hiking roughly 860 miles in New Zealand, she arrived in Nepal ready to tackle the legendary Gokyo Ri Three Passes Trek.

But the challenge she remembers most had nothing to do with altitude, weather, or the terrain.

During the trek, Tatiana found herself dealing with severe altitude sickness while simultaneously becoming increasingly uncomfortable with the behavior of her guide. What began as subtle warning signs escalated into a situation where her instincts told her something was wrong. Ultimately, it was the support of local villagers who stepped in and helped her navigate the situation safely.

Our conversation explores the difference between fear and intuition, why many people wait too long to ask for help, and how communities often show up for us when we least expect it.

Years later, Tatiana still travels, still hikes, and still embraces adventure. The experience didn't make her smaller, it made her wiser.

This episode is about trusting your instincts, building confidence through adversity, and learning that courage often looks less like fearlessness and more like taking the next step anyway.

Craig Weatherup spent nearly 30 years at Pepsi, rising to become CEO of Pepsi-Cola North America and later Chairman and CEO of the Pepsi Bottling Group.

When Pepsi offered him a role in Tokyo, he and his wife Connie made a decision that would shape the rest of their lives. They left comfortable careers, packed up their family, and moved to Japan without ever having visited the country. Then, on Craig’s very first day, he learned his boss had been fired. Two months later, he was given the job. He had 200 employees, barely spoke the language, and was trying to rebuild a business where Pepsi held just 10% market share.

In this episode of Risky Routes, Craig reflects on culture shock, learning to lead through uncertainty, and why the opportunities that define your life rarely arrive with guarantees attached.

On this episode of Risky Routes, Olivia sits down with Keyonna Taylor to discuss the parallels between travel, entrepreneurship, and adaptability. Keyonna reflects on climbing Mount Fuji in Japan and how the experience mirrored the realities of business the hardest parts of a journey are often not where you expect them to be.

Together, they explore agility, customer experience, and why businesses (like travelers) must constantly evolve, pivot, and stay intentional to succeed. The conversation also dives into Keyonna’s perspective on today’s “outcome-based economy” and the danger of companies becoming too comfortable.

On this episode of Risky Routes, Olivia sits down with Dorte Krogh for a conversation about fear, reinvention, nature, and the power of stepping into discomfort.

Dorte shares how a lifelong fear of darkness unexpectedly led her on a transformational journey from sleeping alone in a tent during COVID lockdowns to hiking across Greenland and eventually building leadership retreats that bring executives into nature to reconnect with themselves and others.

The episode explores:

• Overcoming fear through small acts of courage

• Why nature strips away ego and creates authentic connection

• How high performers benefit from slowing down and being present

• Building trust and relationships through shared challenge

• The idea that it’s never too late to redesign your life around what truly fulfills you

Together, Olivia and Dorte discuss how immersive travel experiences can create lasting personal and professional transformation with many participants leaving Greenland making major life changes, launching businesses, deepening friendships, or rediscovering purpose.

At its core, this episode is about intuition, self-discovery, and finding the courage to build a life aligned with who you really are.

On this episode of Risky Routes, Olivia sits down with Jennifer Sertl for an honest conversation about ambition, identity, entrepreneurship, and family. Jennifer reflects on the emotional whiplash of flying from speaking in front of 2,000 people in Osaka, Japan to immediately stepping back into everyday family life at Lambeau Field with her children.

Together, we discuss the hidden trade-offs founders and high performers face, how work can become deeply tied to identity, and why success doesn’t always look the way we think it does. The episode explores balancing career and family, redefining significance, and learning that sometimes the riskiest route is simply believing you are enough.

A riot, a locked gate, and a split-second decision that could have meant life or death.

In this episode of Risky Routes, Brett Miller shares the story of being 23 years old and running the largest security operation in East Timor when a routine day turned into chaos. Called into a UN compound where his own guards had sparked a riot, Brett finds himself surrounded by an angry mob, weapons in hand, with no clear way out.

What follows is a raw, high-stakes moment of fear, instinct, and survival. As panic sets in, Brett leans on a simple but powerful question to shift the dynamic, uncover the real issue, and ultimately defuse a situation that could have ended very differently.

This episode goes beyond the adrenaline. It’s about perspective, communication, and the ability to step into someone else’s reality, even when everything in your body is telling you to run. Because sometimes, the difference between escalation and resolution comes down to whether you choose to react… or to understand.

A $2,500 honeymoon, a one-way leap into the unknown, and a front-row seat to political upheaval.

In this episode of Risky Routes, Adrian Erlinger shares the story of moving to Ukraine with his wife right after getting married armed with little more than a phone number, a few thousand dollars, and a willingness to figure things out as they went. What began as an unconventional adventure quickly escalated into something far more intense, as Adrian found himself reporting on a contentious presidential election, navigating rising political tension, and eventually stepping into a role as an interpreter for international election monitors.

From freezing up in a high-pressure moment of imposter syndrome to finding his footing in a chaotic, unfamiliar environment, Adrian reflects on what it really means to operate when there’s no playbook. This conversation goes beyond travel. It’s about learning that communication isn’t just about words, embracing ambiguity, and realizing that sometimes the most defining experiences don’t give you clarity in the moment… they just push you forward.

She spent years dreaming about climbing Kilimanjaro through setbacks, surgery, and doubt until she finally stood above the clouds.

In this episode of Risky Routes, Leslie Woodward shares a deeply personal journey of resilience, healing, and perseverance as she takes on one of the world’s most iconic climbs. But the real transformation didn’t happen at the summit - it happened along the way, in the quiet, challenging moments that forced her to keep going, step by step.

It’s a story about trusting yourself, leaning on community when you need it most, and redefining what success actually looks like because the most meaningful breakthroughs don’t happen at the top, they happen in the climb.

A 22-year-old with no plan moves to post-Soviet Moscow. What starts as a reckless, “nothing to lose” decision turns into a front-row seat to one of the most chaotic moments in modern history and nearly costs him his life.

In this episode of Risky Routes, Otto Pohl shares how instinct, curiosity, and a series of borderline bad decisions led him from sleeping in a stranger’s childhood bedroom to becoming a New York Times photographer and eventually, to a near-death experience in the middle of a violent coup.

It’s a story about risk, survival, and what happens when everything goes sideways. But more than that, it’s about perspective and how the moments that almost break you can redefine how you see time, opportunity, and what really matters.

Because sometimes the most irrational decisions end up shaping exactly who you become.