#12: Keep Climbing (A Leadership Message I Needed Years Ago)

2025-11-19

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Leadership isn’t a straight ascent, it’s a long, uneven climb.Some days lift you. Others test you. And most leaders, at some point, wonder whether the weight, the pace, and the responsibility are worth it.This final episode of the season is the message I needed 20 years ago: a reminder that the climb is worth it, especially when you stop trying to climb alone.In this episode, you’ll learn how to:- Stay in the climb when leadership feels heavy or unclear.- Recognize the moments where most leaders quit (and how to push ...

Leadership isn’t a straight ascent, it’s a long, uneven climb.

Some days lift you. Others test you. And most leaders, at some point, wonder whether the weight, the pace, and the responsibility are worth it.

This final episode of the season is the message I needed 20 years ago: a reminder that the climb is worth it, especially when you stop trying to climb alone.

In this episode, you’ll learn how to:- Stay in the climb when leadership feels heavy or unclear.

- Recognize the moments where most leaders quit (and how to push through them).

- Build your community of “fellow climbers” who make the journey worth it.

- Reframe the leadership journey as something you don’t have to carry solo.

Trust the process, the preparation, and the person you’re becoming along the way.

This is an honest look at the real journey of leadership: the grind, the gratitude, the doubt, and the deep sense of purpose that makes the mountain worth climbing.

Episode Breakdown:00:00 Intro

05:15 Normalizing the Climb

14:14 What’s in Your Control vs. What Isn’t

19:43 The Myth of Doing It Alone: Why Isolation Is Dangerous

25:11 How Great Leaders Build Community, Accountability & Support

37:34 Where Leaders Should Turn When They Went to Give Up

41:33 Staying in the Climb: Rhythm, Reflection & Resilience

52:21 The Gift of Perspective: Humility, Resilience & Gratitude

56:30 What Kirk Wishes He Knew 20 Years Ago

01:06:00 Thank You to the Team & Community

01:10:06 A Surprise Message for Kirk

01:12:27 Final Reflections & Closing the Season

01:13:52 Outro — Keep Climbing

Subscribe for bi-weekly episodes and visit https://www.dandoadvisors.com/ for coaching inquiries.Resources & Mentions:

Download Kirk's Business Growth Lifecycle PDF: https://www.dandoadvisors.com/resources/business-growth-lifecycle-normalizing-the-scale-journey
Get Coaching from Kirk: https://www.dandoadvisors.com/services/executive-coaching

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