The man who helped copywriters earn $25 million in contracts couldn’t pull the trigger on his own Substack channel.
That’s the confession Kevin Rogers made on Sacred Business Stories this week. And if you’ve ever found yourself knowing exactly what you should do next while watching yourself not do it, this conversation was for meant for you.
Kevin built CopyChief into a powerhouse community over 11 years. Live events with 300 people flying in from Australia and Asia. Legendary industry names jamming on stage at after-parties. A coaching program that actually worked. By any external measure, he’d made it.
Then he walked away from all of it.
The Problem Nobody Talks About
Here’s the conventional wisdom: build the thing, scale the thing, optimize the thing, repeat. Success is a straight line from hustle to growth to more growth.
Kevin’s experience tells a different story.
Somewhere around year seven, the business that used to feel like play started feeling like obligation. His emails had to go through five people before he could send them. He was banned from pushing any buttons in his own software. The guy who built his success on spontaneous connection couldn’t wake up with an idea and share it anymore.
“It started to feel a bit like a machine,” he said. The purity was gone.
This isn’t just Kevin’s story. It’s the story of every creator who followed the playbook perfectly and ended up trapped inside their own success.
The Middle Passage Framework
Kevin discovered a concept from psychologist Dr. James Hollis called the Middle Passage. It works like this:
Your first adulthood is built on one reference point: your childhood. You either try to live up to what you experienced or do the exact opposite. You create roles, chase significance, build identities. This is natural.
Then one day you wake up having achieved everything you set out to achieve, and something whispers: “Is this it?”
That’s not a crisis. That’s an invitation.
Hollis calls it the transition to second adulthood. And the hard part? There’s no workbook. No 90-day calendar with little exercises. No roadmap telling you what the other side looks like.
You just have to let go of any expectation for what life might have waiting for you.
For Kevin, this meant ending a 25-year marriage, closing his business, and sitting in the uncertainty while everyone around him assumed some crime had been committed.
The Real Shift
Carolina asked Kevin a question that stopped the conversation for a minute: “How do you deal with both the spark of inspiration and the need for consistency?”
His answer: “I need to be close to the thing I’m writing about and feeling.”
This is the opposite of what most business advice tells you. Step back. Get out of the weeds. Be the visionary floating in the hot air balloon while your integrator handles the details.
Kevin tried it. He hired brilliant integrators. It never worked.
Because some of us aren’t wired to be separated from our work. We need to feel it in order to create it. And pretending otherwise just delays the inevitable burnout.
The real insight came from Carolina:
“You’re not going to figure it out with your mind. You’re going to figure it out as you walk.”
Kevin wanted that line embroidered on a pillow.
He’s sitting on five completed interviews for his new channel. He knows exactly what he should do. He has a decade of experience telling other people to just start and see what happens.
And he still hasn’t promoted it to his list.
What This Means for You
If you recognize yourself in Kevin’s hesitation, here’s what he said to try:
Pull out a pad and paper. Get away from devices. Write out the things you actually love doing in your business. Then think about how you could emphasize those and shed the rest.
Simple. Not easy.
John Carlton once told Kevin:
“There’s no promise you’ll come back from burnout.”
That warning lands differently for anyone who’s been grinding for years, running launch after launch, building something that somewhere along the way stopped being theirs.
The Declaration
Kevin made a public commitment during the conversation: before his 56th birthday on February 23rd, he’ll release his first episode of Paid to Create on Substack.
I put it on my calendar.
August 18th, 2026, he’s coming back to show us what he built in six months.
If he’s saying any of the same things then, in his words, “I’ll not only be much skinnier because I won’t be eating anymore. I’ll be really annoyed with myself.”
We’re holding him to it.
Where to Find Kevin
Kevin’s been quietly building on Substack and he’s about to go loud. Here’s where to follow along:
Paid to Create — His new channel interviewing creative business founders about the calling, the craft, and the commerce. First episode drops before February 23rd. Subscribe now so you don’t miss it:
Men in the Middle Show — The podcast he co-hosts with Joe DeRoma about navigating the Middle Passage. They recently interviewed Dr. James Hollis himself, the psychologist who wrote the book on second-adulthood transitions. If anything Kevin shared today resonated, start here:
Kevin spent 11 years creating one of the most generous communities in direct response marketing. He’s one of those rare people who made his career by genuinely helping others succeed first. Whatever he builds next, it’ll be worth watching.
One Question Worth Asking
Kevin’s story reveals something that rarely gets said out loud: the gap between knowing and doing isn’t a knowledge problem. It’s a pattern problem.
If you’re stuck in that same loop, wondering why you can’t seem to do the thing you know you should do, maybe it’s time to get curious about what’s actually happening underneath.
The Business Harmony Map takes 5 minutes and shows you which of the 9 fundamental frequencies is creating your sticking point. It won’t tell you what to do. It’ll show you what’s getting in the way of you doing what you already know.
Because Kevin was right about one thing: you can’t think your way to the answer.
You find out who you are by walking.
Thank you Monique Renée, Dennis Berry, Filip Sardi 🌊, Francis Nduati, Karen C-Collector of Books 📖, and many others for tuning into this episode of Sacred Business Stories with Kevin Rogers and Carolina Wilke!
