The Journey On Podcast with Warwick Schiller
Guest: Samantha Osborn
Episode Date: January 23, 2026

Episode Overview

In this fascinating episode, Warwick Schiller sits down with Samantha Osborn: medevac pilot, adventurer, horsewoman, and sailing enthusiast. Samantha’s life story is a blend of northern wilderness, aviation, horsemanship, and intrepid world travels—often alongside her husband, fellow adventurer Jesse Osborn (featured in a previous episode). Throughout the conversation, themes of self-discovery, courage, relationship growth, and lessons from living in remote places are interwoven with extraordinary tales from the Arctic, the open ocean, and beyond.

Key Discussion Points & Insights

Samantha’s Early Life and Adventurous Upbringing

• Arctic Childhood & Family Influence
  • Grew up in Ontario, then moved to Yellowknife, Northwest Territories as a teen.
  • Father was a pilot working in the Canadian High Arctic—flying Medevac and supply missions to isolated communities (03:08–13:00).
  • Childhood included frequent travel into remote Arctic settlements, fostering a lifelong comfort with “the middle of nowhere.”

    “I recognized that I still like places that people would describe as being in the middle of nowhere. And to me, they are somewhere because I live there and I know the people that live there.” — Samantha (07:50)

• Family Adventuring
  • Both parents valued adventure, travel, and experience over convention. (34:54)
  • Moved frequently, visited Europe, and embraced unconventional, unstructured lifestyles.

Immersed in Arctic Life & Culture

• Insights into the Inuit & Life in the Far North
  • Described Inuit culture, including nomadic traditions, the creation of settlements by government, and unique foods and customs (14:45–24:51).
  • Experiencing contrasts: kids who had never seen trees, extreme cold, and constant darkness (18:46).
  • Encounters with traditional igloos and Inuit hospitality.

    “I was so welcomed that I didn’t even consider that I would have any danger there. Which is weird, because you’re right, it’s very sparse.” — Samantha (28:41)

• Self-Reliance in Harsh Environments
  • Recalled anecdotes showing the calm resourcefulness of Arctic residents when confronted with blizzards and isolation (29:17–32:11).
  • The lesson: true acceptance and adaptability in the face of difficult conditions.

    “That ability to just be so comfortable in a place that you don’t have a destination... you have what you need right there, that is just so amazing to me.” — Samantha (31:41)

• Unique Diets
  • Tasted traditional foods such as Arctic char and fermented meats (“like beef soaked in rancid salmon oil for a while”)—not for the faint-hearted! (21:07–23:30)
  • Shared about the social importance of hunting, drying fish, and festive communal meals.

Journey into Aviation

• Path to Becoming a Pilot
  • Inspired by her father but started flying later, in her 20s (22:09–23:19).
  • First career steps included work in remote mining camps before pursuing her license.
  • Learned on the job in Yellowknife; embraced challenging bush flying—on floats, skis, and tundra tires—across the far north (65:06–66:07).

    “I loved moving. I loved that the airplanes came and went, that it had a purpose, and it finished at the end of the day and you weren’t at a desk...” — Samantha (06:33)

• Adventures in Remote Aviation
  • Detail of flying supplies, scientists, and medevac missions to communities beyond the end of the road (41:08–46:49).
  • Orange garbage bags filled with snow as temporary runway markers. (65:06–65:14)
• Current Life as a Medevac Pilot
  • Now based in Roswell, New Mexico, enjoying the flexibility and change of scenery (02:41–03:12).

Remote Places, Wild Animals, and Tales of the North

• Life in Yellowknife & Remote Camps
  • Move to Yellowknife as a teenager was “shell-shocking,” but grew to love the isolation and wildness (53:53–54:21).
  • Worked in Arctic mining, witnessed wildlife (wolves, wolverines, bears, caribou).

    “It was incredible. I got to see wildlife... saw a wolf from 30ft away. It was incredible.” — Samantha (55:13)

  • Close encounter stories: wolverine walked right past her, wolf locked eyes with her, and observing grizzly bears from the air (55:48–61:35).

Meeting Jesse: Adventure Meets Adventure

• Sailing and Romance in the High Arctic
  • Story of meeting Jesse Osborn while flying aerial wildlife surveys (searching for musk ox) over Victoria Island; spotted his sailboat at Cambridge Bay—the only boat in the harbor! (67:07–69:07).

    “I remember he just, like, sparked with energy, you know.” — Samantha (70:42)

  • Their relationship blossomed quickly; Jesse was in the midst of sailing through the fabled Northwest Passage, making him only the 254th person to do so (66:18).
  • Samantha joined his Arctic adventure, finishing the Northwest Passage voyage together and sailing to Greenland (78:06–83:27).

    “We encountered a lot of ice that year… and I saw a bowhead whale. It's still one of the coolest experiences I've ever seen.” — Samantha (81:10)

  • Life as a sailor followed, from Alaska to trans-Pacific races and running a sailing business.

Lessons in Relationships & Personal Growth

• Navigating Life Transitions

  • After years of travelling and working together, they bought land in remote Pie Town, New Mexico, but faced new challenges: Jesse's unhappiness away from sailing, the struggle to adapt, and reinventing their marriage (92:07–95:47).

    “We really had to reinvent our marriage to see how it works. That's been different… worth it. And we're coming out the other side.” — Samantha (95:00)

  • Samantha credits therapy, embracing emotional vulnerability, and “reparenting” with transforming their relationship.

    “Learning that it wasn’t the end of the world... Conflict is actually good. Having disagreements is normal.” — Samantha (100:55)

  • Noted parallels between horsemanship (calming anxious horses) and self-regulation in human relationships.

• Wisdom & Reflection

  • Discussed Esther Perel’s idea that you may have many relationships within a lifetime, often with the same person—due to growth and change (96:19).
  • Warwick draws parallels to horse training: prevention and repair involve the same principles, whether with horses or in marriage (98:47).

Quickfire Q&A & Memorable Takeaways

• Most Recommended Book
  • The Seven Principles for Making Marriage Work by John & Julie Gottman.

    “It's just good on how to live with humans, not just marriages.” — Samantha (104:53)

• Unexpected Enjoyment
  • Loves the Dungeon Crawler Carl audiobook series (RPG-lit genre)—a fun, wild escape from her usual reality (106:16).
• Admired Quality in Others
  • Earnestness—the thoughtful, kind, nonjudgmental perseverance exemplified by Jane Goodall (109:18).
• Relationship with Fear
  • Has learned to acknowledge and befriend fear as an ally, using mindful techniques borrowed from horsemanship in her high-risk aviation work (112:45).

    “Fear is an ally and not something to suppress or ignore... Thank you, fear. I acknowledge you. Deep breaths.” — Samantha (115:47)

• Regrets
  • Wished she’d been braver in relationships earlier and encourages others to share themselves more openly (115:56).

    “I really regret not trusting more and not really diving into relationships... I hope in the future to just make sure that the people I meet are able to be themselves around me.” — Samantha (115:56)

Notable Quotes & Memorable Moments

• On Being Adaptable:
  “Their ability to adapt to the circumstances that are around you, right where you are without striving, that makes that story so beautiful… they’re totally comfortable and accepting of the environment that they’re in, and that is where they belong.” — Samantha (32:52)

• On Personal Growth:
  “All the things I did with Henry [her horse] to help him realize he’s safe… I look back now and I’m like, oh, that’s what I’ve been teaching myself.” — Samantha (98:47)

• On Relationship Reinvention:
  “You have relationships—like three or four big relationships in your lifetime—and often they're with the same person.” — Samantha, quoting Esther Perel (96:33)

• On Wilderness:
  “I like places that people would describe as ‘the middle of nowhere’, and to me they are ‘somewhere,’ because I live there.” — Samantha (07:50)

Standout Segments & Timestamps

• Intro & Samantha’s Background: 00:44–06:33
• Life in the High Arctic: 10:00–24:51
• Exploring Inuit Culture & Survival: 13:00–32:11
• Life Lessons from Isolation: 28:41–34:27
• Mining Camp & Wildlife Encounters: 55:13–61:35
• Journey into Aviation: 62:56–66:07
• Meeting Jesse & Beginning Sailing Adventures: 66:18–71:36
• The Northwest Passage Voyage: 78:06–83:27
• Pie Town, NM – Relationship Struggles & Growth: 92:07–96:19
• Therapy, Emotional Intelligence, Parallels to Horsemanship: 98:47–104:36
• Q&A: Books, Fear, Regrets, and More: 104:53–117:10

Final Thoughts

A rich, engaging conversation brimming with tales from the Arctic, lessons from the land and sea, and reflections on what it means to grow, adapt, and deeply connect—both with others and with oneself. Samantha’s humility, warmth, and openness shine through, providing inspiration for anyone drawn to the edges of the map, or to the edges of their own personal growth.

For more on horsemanship, personal development, and authentic connection, follow Warwick Schiller and the Journey On Podcast.