When to Win a Client Back—and When to Walk Away
Revised on June 2025
Sometimes the hardest part of running a client-first agency isn’t the pitching, the planning, or the execution; it’s knowing when to hold on, and when to let go. We’re not just talking about contracts or scopes of work; we’re talking about relationships.
At YellowDog, we’ve seen both sides: the satisfying win of bringing a client back, and the tough-but-right decision to part ways with one. Here’s a short story that reminded us just how important that balance is.
The Text That Made Us Pause
A few weeks ago, we got a simple text from a former client:
“Hey, let’s chat.”
No context, no details, just six short words that sparked a flood of memories.
We’d worked with them for years. We helped build their brand from the ground up. We cheered their successes and problem-solved through challenges. And then… things slowed. Budgets tightened. They brought more things in-house. Eventually, they moved on.
That was two years ago.
What We Felt in That Moment
We were excited, of course we were. But we also paused.
The easy answer would be: “YES, we’d love to work together again.”
But instead, we took a moment to ask ourselves:
- Why did they leave in the first place?
- What’s changed on their side, and ours?
- Will this be a quick project or a long-term fit?
- Are our values still aligned?
It’s Not Just About the Work
One of the hardest truths we’ve learned over the years: not every client is a fit forever. Sometimes it’s budget. Sometimes it’s chemistry. Sometimes the needs evolve in ways we can’t meet without compromising how we work, or who we are.
And that’s okay.
We Said Yes—But With a Plan
This client came back with clarity. They’d grown. They wanted strategy, not just tactics. They were ready to invest, not just money, but trust. We said yes, because it felt like a fit, not just a gig.
Letting Go Can Be the Best Move
We’ve also said no. To opportunities that didn’t feel right. To relationships that had run their course. It’s hard. It can feel like failure. But sometimes, saying no is the most respectful and strategic thing you can do for both parties.
Final Thought
Winning a client back is great. Letting one go with respect is powerful. Knowing the difference? That’s where the real wisdom comes in.
If you’re looking for a partner who knows how to balance trust, strategy, and results, we’re here.
Let’s talk about what a thoughtful, forward-looking partnership could look like for your brand.