When Your Biggest Win Happens on Your Worst Day

Here's something I don't see talked about enough: the psychological complexity of running an agency.

I'm not talking about stress. Everyone knows agencies are stressful. I'm talking about the mental gymnastics required when contradictory things happen simultaneously.

Your biggest client win lands on the same day your creative director gives notice. You hit record revenue, then realize your personal comp actually went down because margins compressed. You launch the best work your team has ever produced, and three hours later you're having a difficult conversation about cash flow.

This isn't occasional. This is the operating rhythm.

You're supposed to celebrate with your team while privately processing that the math doesn't work anymore. You're supposed to project confidence while genuinely uncertain about next quarter.

I've been through this cycle enough times to know it doesn't go away. You don't level up out of it. The stakes just get higher.

When I'm evaluating acquisitions now, I try to read between the lines for this. A founder who seems tired but their numbers look fine? There's usually an invisible weight they've been carrying. Revenue doesn't tell you about the emotional roller coaster happening behind it.

If you're in this right now—simultaneously winning and losing, growing and struggling—just know that's normal. It's not a sign you're doing it wrong. It's just agency ownership.

Be a little easier on yourself. And maybe be a little easier on the next agency owner you talk to.

I've been watching how creative work is evolving, and there's a pattern worth paying attention to.

The best designers I worked with over the course of my agency career weren't just visually talented—they had deep technical mastery of their tools. They knew Illustrator and Photoshop inside and out. Complex creative work demanded it.

The shift: That same principle still holds, but the tools are changing underneath everyone.

Node-based workflows are becoming standard. Figma is integrating them. The technical skills that made someone a standout five years ago aren't the same skills that will matter five years from now.

The approach: If you're running a creative team, audit where your technical training is focused. Are you still optimizing for single Adobe product mastery while the industry moves toward node-based, integrated workflows?

The outcome: The agencies that adapt their technical development—not just their creative vision—will have a real edge. Tool mastery still matters. It's just different tools now.

There's a narrative floating around that AI will make creative work less technical. That tools will become so intuitive that deep expertise won't matter.

I'm seeing the opposite.

The designers and creatives who are thriving right now are the ones leaning into technical complexity—learning node-based systems, understanding how to work alongside AI tools, building workflows that integrate multiple platforms.

This isn't about replacing creativity with technical skills. It's about the bar for technical fluency rising across the board. The creative who can concept and execute in modern tooling has more leverage than ever.

For agency leaders: this changes how you hire and how you train. Pure aesthetic talent without technical adaptability is becoming a riskier bet.

I've been sitting with a question lately: how do you build resilience into an agency's culture—not just its operations?

Systems and processes help. EOS helps. But the psychological weight I mentioned earlier? That's harder to systematize.

Ready to build a more resilient agency culture? If you've found something that works—a practice, a rhythm, a framework for the emotional side of this—I'd genuinely like to hear it. Hit reply and let me know.

That's all for this week.