We’ve all been there.

You hire a freelancer who drops the ball.

You work with a client who ends up being a nightmare.

You try a new approach to delivering a project and end up losing money.

The natural reaction is to protect yourself. You generalize.

“Freelancers can’t be trusted.”

“Clients are difficult.”

“We’re never doing that kind of project again.”

But here’s the problem: you’re learning the wrong lesson.

You’re reacting to a bad sample. And worse, you might be letting that single data point reshape your entire playbook.

If you stop to look closely, what actually happened?

Was it the freelancer, or the way you sourced, vetted, or onboarded them?

Was the client fundamentally bad, or were there red flags you ignored?

Was the project model flawed, or was it the way your team executed on it?

There’s value in asking those questions. Not to blame, but to learn.

What was in your control? What wasn’t? What will you do differently next time?

Instead of tossing the whole category (freelancers, clients, project types, etc.) into the “never again” bin, zoom in. Get specific. Look for patterns over time, not anecdotes.

This kind of thinking takes discipline. But it pays off.

Let’s take freelancers.

It often takes working with dozens before you find someone great. Someone who communicates clearly, meets deadlines, and brings real craft to their work.

If you get burned early and decide, “freelancers don’t work for us,” you cut yourself off from a massive talent pool. Worse, you might settle for a mediocre one, just because they’re okay and they get the job done, sort of. But you never fully trust them with more. So you end up doing more yourself or overburdening your team.

The better move? Set a high standard.

Cycle through candidates who don’t meet it.

Keep testing, interviewing, and refining your vetting process.

Yes, it’s work. But the upside of finding someone exceptional is worth it. You earn back time, flexibility, and leverage.

This principle applies across the board:

“We tried AI. It made too many mistakes. Let’s not waste more time.”

“We hired a salesperson once. Didn’t work out.”

“We gave team members more autonomy, but someone dropped the ball.”

In each case, the temptation is to take the one bad outcome and close the door. But that’s how you stop evolving. That’s how teams stagnate. That’s how you build a culture of risk aversion.

Instead, treat each new initiative, hire, or tool as a system to improve, not a bet to either win or lose.

More reps give you more data. More data makes your filters sharper. More filters give you better outcomes.

That’s how you grow, that's how you develop better decision-making skills as the leader of your agency.