Develop a Philosophy of Trouble

In this special Revenue Builders Rewind episode, we revisit our powerful first conversation with Doug Holladay, CEO & founder of PathNorth and author of Rethinking Success: Eight Essential Practices for Finding Meaning in Work and Life. Doug shares his unconventional career journey and explores his philosophy on leadership, purpose, and living a more intentional life.

The discussion dives into the importance of authenticity, gratitude, and meaningful relationships, as well as the value of understanding your own story and embracing vulnerability. Doug also highlights why many people need to rethink how they define both personal and professional success. He offers practical exercises for uncovering purpose and explains how simple rituals can help ground your life in reflection and gratitude.

Stay tuned for more episodes with Doug as we continue our series with him in 2026.

ADDITIONAL RESOURCES

Connect with J. Douglas Holladay:
https://www.linkedin.com/in/dougholladay/

Listen to the earlier episodes with Doug - each one delves into a different aspect of successful business leadership: 

The Power of Gratitude: https://www.forcemanagement.com/the-power-of-gratitude-an-in-depth-discussion-with-douglas-holladay

Knowing Your Story: https://revenue-builders.simplecast.com/episodes/know-your-story-to-achieve-true-success-with-doug-holladay

Rethinking Success and Finding Purpose: https://www.forcemanagement.com/rethinking-success-and-finding-purpose-with-doug-holladay

Learn more about Doug’s CEO programs: https://www.pathnorth.com/

Read the Guide on Six Critical Priorities for Revenue Leadership in 2026: https://hubs.li/Q03JN74V0

Explore Force Management’s Free SKO Planning Resources: https://hubs.li/Q03K94cs0

Enjoying the podcast? Sign up to receive new episodes straight to your inbox: https://hubs.li/Q02R10xN0

HERE ARE SOME KEY SECTIONS TO CHECK OUT

[00:03:38] Finding Purpose and Passion
[00:04:27] Understanding Life Patterns
[00:07:17] The Impact of Family Stories
[00:18:48] Authentic Leadership and Vulnerability
[00:34:10] The Importance of Knowing People's Stories
[00:37:30] Understanding Personal Stories
[00:38:34] Pandemic-Induced Self-Reflection
[00:39:31] Pain as a Catalyst for Change
[00:41:14] Traits of Great Leaders
[00:46:08] Founding PathNorth
[00:56:55] The Power of Gratitude
[01:03:24] Rapid Fire Questions

HIGHLIGHT QUOTES

[00:04:22] “Put your life in five-year blocks... What did you love doing and what did others say you were good at?”
[00:06:59] “Most of us get eclipsed by the money chase.”
[00:07:59] “If you don’t create space to think and feel, you’ll be one of those whose light goes out.”
[00:10:50] “We’re all born in someone else’s story.”
[00:13:21] “The story you have seen will be your family unless you break those patterns.”
[00:16:13] “Our point of identity is not our strength, it’s our brokenness.”
[00:18:37] “Meaning is what you want to go for. You can be in the most godawful situations and still find meaning.”
[00:22:17] “Everybody has a story. The most successful people are the ones who let people tell their stories.”
[00:27:09] “When the price of making more begins to do bad things to my soul, it’s time to leave.”
[00:28:40] “Gratitude is the only emotion that cannot share space with any other emotion.”

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