Risky Routes

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.

Ep 13 The Cost of Crossing Borders for Work and Family with Jennifer Sertl

On this episode of Risky Routes, Olivia sits down with Jennifer Sertl [https://www.linkedin.com/in/jennifer-sertl-922177/] 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.

Ep 12: Surviving a mob in East Timor with Brett Miller

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 [https://www.linkedin.com/in/brettdavidmiller/] 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.

Ep 11: Honeymooning in Ukraine with a side of political protests with Adrian Erlinger

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 [https://www.linkedin.com/in/adrianerlinger/]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.

Ep 10 Lessons in entrepreneurship from hiking Kilimanjaro with Leslie Woodward

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 [https://www.linkedin.com/in/leslie-woodward-4891a631/] 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.