Does What I'm Doing Really Matter? A Conversation With Chad Brown

What if the questions you’re avoiding are the ones that hold the most meaning? Chad Brown joins the podcast for an honest, unfiltered conversation about purpose, grief, and self-trust — sharing raw reflections that offer a refreshing perspective on navigating uncertainty and building relationships rooted in truth. He explores the weight of small decisions, the paradox of wanting clarity while resisting life’s invitations, and how loss has reshaped his understanding of what truly matters. From the tension between ambition and presence to the challenge of staying in integrity with ourselves, this episode dives into the messy, beautiful reality of being human — and the courage it takes to live into the unknown.

Chad Brown is a scaling strategist and coach who helps creative entrepreneurs increase profit while working less. He founded Shade Tree Films in 2008, working with brands like Volkswagen, Target, and Pixar before selling the company in 2021. Passionate about leadership and business, he has spent the last seven years mentoring entrepreneurs in creating more freedom in their work. When he's not coaching, Chad is off on wild adventures in the mountains with his family. He lives in Orem, Utah, with his wife, Katie, and their three children, Addison, Kenya, and Milo.

Connect with Chad:

• Chad’s LinkedIn: https://www.linkedin.com/in/chad-brown-founder-freedom/
• Chad’s Email: [email protected]
• Chad’s Website: https://www.founder-freedom.com/

Key Topics Discussed:

0:00:00 – Intro

0:03:57 – The Heart of Connection

0:06:18 – The Question Chad is Living Into

0:10:22 – Grief and Re-evaluating Life’s Meaning

0:13:26 – The Disappearance of a Loved One

0:19:12 – Mourning Together: A Different Approach to Grief

0:22:39 – Wisdom Without the Chaos

0:25:13 – The Wave Called Grief

0:34:49 – Shifting Survival Strategies

0:39:19 – The Risk of True Belonging

0:43:53 – What Is Safety, Really?

0:48:02 – Living with Integrity

0:53:23 – Love, Promises & Parenthood

0:55:35 – Self-Love & Showing Up for Others

0:58:32 – The Small Choices That Shape Us

1:04:34 – Anticipating Discomfort vs. Experiencing It

1:06:07 – You’re Never Done Arriving

Resources:

• Website: https://www.ckoesterinspired.com
• Podcast IG: https://www.instagram.com/livingthequestionspodcast
• Business IG: https://www.instagram.com/ckoesterinspired
• Coaching Offerings: https://www.ckoesterinspired.com/coaching-offerings

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