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

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

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

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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

CONNECT WITH US

  • www.decidedlypodcast.com

  • Join us on Instagram: www.instagram.com/decidedlypodcast

  • Join us on Facebook: https://www.facebook.com/decidedlypodcast

  • Shawn’s Instagram: www.instagram.com/shawn_d_smith

  • Sanger’s Instagram: www.instagram.com/sangersmith

MAKING A FINANCIAL DECISION?

At Decidedly Wealth Management, we focus on decision-making as the foundational element of success, in our effort to empower families to purposefully apply their wealth to fulfill their values and build a thriving legacy.

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