The client has been with you since year one. Pays on time. No real drama. Also questions every invoice, slows down every approval, and makes every project harder than it should be. You keep them anyway, because letting go feels like ingratitude. And because the revenue feels safe. Because the hard thing is always easier to put off until next month.
I kept one of those clients for almost thirteen years.
He came to me in the early 2000s through a mutual friend. Small project, small budget, right at the edge of what I knew how to do at the time. I said yes because I was hungry and it was real work and someone was trusting me with it. I built what he needed, and then I kept building. Kept maintaining. Kept showing up.
When I moved to an agency, he came with me. When I started my own firm, he was still there.
Loyal. Always paid. Never any real drama.
The problem was that over thirteen years, I had changed. My skills had grown. My pricing had grown. My understanding of what good work actually requires had grown. He wasn’t growing with any of it. He’d question costs, hold up approvals, resist the decisions that served the work and push for the ones that didn’t.
He wasn’t a bad person at all, he just wasn’t the right fit for me anymore.
For longer than I’d like to admit, I kept that from myself. He was my first real client. He’d been loyal. And underneath the sense of obligation, if I’m being honest, was fear. Fear that letting go of something certain – even a small, difficult, increasingly frustrating certain thing – meant something was wrong with me.
Eventually I made one of the harder calls in my business life. I told him we were going to stop working on his project, refund his remaining balance, and step aside so someone else could take it forward.
The last time I checked, he still has a site that does what he wants it to do. He never launched the redesign we’d been building together. And I’m ok with that.
Holding on out of loyalty sounds noble. Most of the time it’s just fear with better branding. It doesn’t serve the client. It doesn’t serve you. It keeps you both a little stuck and neither of you moving.
When I sit with agency owners, this is one of the first places I look. Who are you keeping out of obligation? Who have you outgrown but haven’t said so yet? What would it actually mean to create that space?
The clients who were right for you at the beginning are not always the clients who are right for where you’re going. That’s not failure. That’s just what growth looks like.
Loyalty is a real thing, but fear dressed up as loyalty is something else entirely.
I hope you learn the difference a little earlier than I did.
👋 I’m Clint. I help your right-hand person step into confident decision-making, freeing up space for you to focus on your agency.👋 I’m Clint. I help your right-hand person step into confident decision-making, freeing up space for you to focus on your agency.
Work with me!