Lessons From a Bruised Ego

Chasing White Rabbits | Chapter Four

There are moments in every leader’s journey when you feel invincible. Your methods are proven, your record untarnished, your confidence unshakable. And then, out of nowhere, reality delivers a gut punch.

For me, it came in the form of the most difficult client I’d ever worked with. This is the story of that client. Of my bruised ego, my own shortcomings, and a solution we were lucky to find. It’s not a story of failure but of lessons learned—lessons I’ll carry with me for the rest of my life.

For seven years, our rebranding process was unbeaten. It wasn’t just good; it was genius. Carefully crafted to remove personal bias and subjectivity, it delivered clarity and results every time.

This wasn’t by chance. I’d spent years refining the process to ensure it worked under any circumstances. We went from presenting multiple logo options to offering a single agency recommendation, built on the foundation of strategic insight and expert execution.

This shift was significant. It raised the stakes—and the expectations. When you put forward one option, you have to be right. The responsibility is enormous. But the risk? The reward.

And the results proved it. We transformed modest projects into lucrative six-figure engagements, turning rebranding into one of the agency’s most profitable services. I’ll admit it: I drank the Kool-Aid. Seven years undefeated. Until we weren’t.

When the chance came to pitch for a dream client—a unicorn in their industry—I broke my usual rule. I rarely answer RFPs, and I never do spec work. But this one was different.

The opportunity was extraordinary. It wasn’t just a chance to work in an industry we loved; it was a chance to compete against the very best. And when we won the bid—beating out two of the most renowned brand agencies—I allowed myself a rare celebration.

I imagined this project would be one for the books, a crowning achievement for our team.

Thirteen months later, I called our CEO and said, “I’m out.”

The project was snake-bit from the start. Five months of silence after signing the contract left us in limbo. Fifty-five iterations followed—each scrutinized, rejected, and contradicted. We restarted the process three times, only to end up back at square one three times.

The process that was supposed to remove subjectivity? It crumbled. This client had no logical rationale, continually contradicted themselves, and lacked big-picture thinking. They were driven by whims and personal preference, bolstered by the wrong yes-men in the wrong seats.

To their credit, they were wonderful human beings. But I’d never felt more defeated.

Not only had my undefeated process failed, but I’d also failed to lead us through the storm. My team was confused. I was furious—not because we didn’t deliver, but because we did. The work was brilliant. The strategy was sound. And yet, it wasn’t enough.

When I told our CEO I was ready to void the contract, he backed me without hesitation. “I support you,” he said. “But let me see what we’ve done so far.”

He called me back 24 hours later. “This is outstanding work,” he said. “A game changer. Try one more time. And then, if it doesn’t work, I’ll pull the plug.”

That support had the opposite effect of what I expected. Instead of validating my decision to walk away, it reignited something in me. Hell no, I thought. We’re not going down like this.

If Chapter 3 taught me anything, it was that perseverance can change everything. This was one of those moments. One last shot. Everything we’ve got.

This time, I did something different. I stepped back.

I opened the project to our entire agency network, stripped away every preconceived notion, and issued a challenge: a 24-hour design sprint. Writers, designers, art directors, and account staff all rallied together, overnight, to create as many fresh concepts as possible.

The result? Thirty new, market-ready brand identities. The team was energized. The process was reinvigorated. And, in the end, it finally produced a winner.

Ironically, the final direction the client chose ignored three fundamental rules they’d outlined at the beginning. I almost didn’t include it in the presentation because it was so blatantly against their original criteria. But at that point, why not? The fact it saved the day was a lesson in itself.

What mattered most was that we found a solution—and the project was finally complete.

When I look back on this experience, what stayed with me wasn’t the win (or the loss)—it was the process of getting there. It forced me to confront my own shortcomings and evolve as a leader.

When you’re ready to give up, go back one more time with a Hail Mary and break every rule you know. It’s often at this moment, reckless passion will light the path.

Don’t let your ego block the solution. Sometimes, the answer lies in someone else’s perspective… and that’s okay. Run with it.

Leadership isn’t about being in control; it’s about enabling the best outcome—even if it means stepping aside. And sometimes you must.

In that moment, I realized something new. Leadership isn’t always about being at the front of the battle. Sometimes, it’s about pulling the right strings at the right time, making the hard decisions, and giving others the chance to shine.

Because at the end of the day, the agency’s success mattered more than my own.

Every leader faces moments like this—moments that challenge everything you thought you knew. My bruised ego taught me something invaluable: sometimes, it’s not about protecting your record or your pride. It’s about being strong enough to find the solution, no matter what it takes.

After all, the mark of a true leader isn’t perfection. It’s perseverance. And sometimes, what defies convention is the one thing that saves the day.