Ep. 186: Deciding to Hike Your Own Hike: Lessons from the Trail About Business, Belonging, and Becoming

What does a 500-mile trek through Spain, a rain-soaked trail in Scotland, and a solo summit in Colorado have to do with building a meaningful life or business?

In this episode, we share the unexpected lessons learned from long-distance hikes, Ironman races, and conversations on the trail — and how they mirror the journey of entrepreneurship, leadership, and self-discovery.

From the spiritual silence of the Camino de Santiago to the muddy mess of the West Highland Way, this isn’t just a story about hiking — it’s about purpose, progress, and the people who walk beside us (or don’t).

If you’ve ever felt like the finish line didn’t fulfill you… this one’s for you.

KEY TOPICS

• “Hike your own hike”: What this means for life, business, and ignoring the noise

• Why the journey is the reward — not the goal or the finish line

• What hiking in the rain teaches us about embracing discomfort

• The real reason entrepreneurs hesitate to sell their businesses

• How solitude reveals what you’re actually chasing

• The power of walking with the right people, not just anyone

• The Camino de Santiago’s secret economy, sacred history, and soul-deep meaning

• How to follow the right signs — and know when someone else’s path isn’t yours

CHAPTERS

• 00:00 Introduction

• 00:51 Hiking in Scotland: The West Highland Way

• 02:18 Hiking Etiquette and Annoyances

• 03:28 Conquering Colorado's Fourteeners

• 07:51 The Spiritual Journey of the Camino de Santiago

• 14:44 The History and Experience of the West Highland Way

• 16:54 Group Hiking Dynamics

• 20:35 The Pressure to Grow in Business

• 21:07 Redefining Success: Progress Over Growth

• 21:50 A Lesson from the Parish Priest

• 22:56 Zappos' Unique Hiring Practice

• 23:59 The Importance of Human Connection

• 27:17 The Journey is the Reward

• 33:53 Lessons from Hiking

• 38:31 Embracing Hardship

• 41:21 Final Thoughts on Hiking and Life

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