Inside the Absurdity of the Iraq War with Christian Caryl, former Op-Ed Editor at the Washington Post

Inside the Absurdity of the Iraq War with Christian Caryl, former Op-Ed Editor at the Washington Post

Most people experience history through headlines. Christian Caryl [https://www.linkedin.com/in/christiancaryl/] 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.

I Had to Escape My Trek Guide in the Himalayas with Tatiana Fofonova (CEO and Cofounder of Koda Health), S2 E17

The most dangerous part of Tatiana Fofonova [https://www.linkedin.com/in/fofanova/]'s trek through Nepal wasn't the mountain. Before setting off on a year of solo travel, Tatiana (CEO and Cofounder of Koda Health [https://www.kodahealthcare.com/]) 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.

S2 Ep 16: The Risk that Built a Pepsi CEO with Craig Weatherup, former CEO of Pepsi North America

Craig Weatherup [https://adkcommunityfoundation.org/team-member/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.

Ep 15 Climbing Mount Fuji and Escaping Comfort with Keyonna Taylor

On this episode of Risky Routes, Olivia sits down with Keyonna Taylor [https://www.linkedin.com/in/keyonnataylor/]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.

Ep 14 How Sleeping Alone in a Danish Forest Changed Her Life with Dorte Krogh

On this episode of Risky Routes, Olivia sits down with Dorte Krogh [https://www.linkedin.com/in/dorte-krogh-52b0991/] 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.