What does it mean to have more number one songs than anyone in country music history and still struggle with sleepless nights, wondering if any of it matters?

What if the machine everyone thinks you are is actually just a person trying to figure out why they're here?

Ashley Gorley has written more number-one songs than anyone in country music history. His work has shaped the sound of modern country music through hits recorded by Luke Bryan, Carrie Underwood, Blake Shelton, Morgan Wallen, and countless others. But the numbers don't tell his story.

Ashley grew up in Danville, Kentucky, a small farm town where sports were everything and nobody he knew loved their job. He moved to Nashville for college, then spent eleven years grinding before his first real success. He has built a career on a simple goal: to write "songwriter" on his taxes.

Despite achieving what most would consider impossible, including 85+ number one songs, induction into the Songwriters Hall of Fame, and running one of Nashville's most successful publishing companies, Ashley found himself wrestling with the weight of wondering what it all means.

Partnering with The Onsite Foundation, the success of the hit "I Am Not Okay" with Jelly Roll funded the Creatives Support Network, a place where songwriters can process their stories and struggles in a therapeutic space for no charge.

Today's conversation is an honest look at what it takes to stay human when everyone expects you to be a machine, how to carry success without letting it carry you, and why the best legacy has nothing to do with the songs you write.

In this conversation, you'll learn:

How to Navigate Rejection Even at the Top of Your Field

How Your Greatest Compliment Might Have Nothing to Do With Your Career

How to Set Goals You Can Actually Control

How to Recognize When Being "Used" Is Actually Okay

How to Build Time for Vulnerability Into High-Pressure Creative Spaces

How to Dissolve Yourself and Write for Someone Else's Voice

How to Protect Your Family When Your Career Demands Everything

How to Process the Gap Between Achievement and Fulfillment

How to Turn Success Into Service for Your Creative Community

Welcome to Human School, where we learn what matters most. - Miles Adcox

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What We Discuss:

00:01:38 Ashley Gorley: Introduction

00:07:03 Growing Up in Danville, Kentucky: Where Sports Were Everything 

00:14:18 The ACL Tear That Changed Everything 

00:17:08 The Moment He Discovered Songwriting Was Actually a Job 

00:19:01 The Eleven-Year Grind Before Anything Made Money 

00:21:13 The Truth About Networking in Nashville

00:26:00 When the Spotlight Gets Too Bright: Protecting Privacy in a Public Industry 

00:30:05 Why Being Critical of Songs for a Living Makes Life Harder 

00:38:35 The Counterbalance: His Wife 

00:41:09 Curating Environments vs. Living in Them—The Trap of High Expectations 

00:43:17 The Myth That You Have to Choose Between Success and a Life 

00:49:03 Why "I Am Not Okay" Became More Than a Song

00:52:08 The 95% Rejection Rate Nobody Talks About 

00:58:11 Never Set Goals You Can't Control—The Wisdom That Changed Everything 

01:03:53 His Daughter's Hall of Fame Speech: The Greatest Thing Ever Written About Him 

01:06:15 Why Being Present Matters More Than Being Prolific 

01:09:34 The Myth of the Machine—And the Human Behind the Hits 

01:14:05 Opening the Door to Vulnerability in the Writing Room 

01:18:03 Writing "I Am Not Okay"—The Ten-Minute Freestyle That Became a Movement 

01:21:29 The Creative Support Network: Fully Funded Therapy for Struggling Songwriters 

01:29:30 The Struggle He Still Can't Shake: "Does This Even Matter?" 

01:31:30 Go After Your Core Relationships the Way You Go After Your Career 

01:34:25 The Moving Target of Success and Why Small-Town Sideline Parents Might Have It Right