How to Successfully Screw Something Up

Six years ago, I made what I believed was one of the biggest mistakes of my leadership career.

I had spent months redesigning a master schedule for 900 students. We researched, listened, planned, and communicated—and when we finally implemented it, it didn’t work.

Not needs-a-few-tweaks didn’t work—it epically did not work.

For the next five years, I filed the “zipper schedule debacle” under Things Jessica Cabeen Should Never Do Again. Then, right before the start of this school year, I ran into two teachers who had lived through it with me. Somehow, the zipper schedule came up in conversation, and I immediately responded the way I always did when someone mentioned it: “Yeah. That did not go well.”

Their response surprised me. What I remembered as an epic failure, they remembered differently. One of them said, “You were the first administrator in my 20 years of teaching who owned a mistake. We still talk about that.” I had spent five years remembering the schedule, but they remembered what happened afterward.

I left that conversation seeing the entire experience differently. The mistake was still a mistake. The schedule still hadn’t worked. But maybe the most important leadership lesson wasn’t in getting it wrong. Maybe it was in what happened after I did.

Thankfully, it doesn’t take messing up an entire middle school schedule to learn this lesson. Big mistake or small, what leaders do next matters. Here are four ways a mistake can become more than something we regret and actually make us better leaders.

Step 1: Own It

I am not sure when leaders started to confuse confidence with certainty—the idea that being in charge means having the right answer, right away. But when something goes wrong, trying to defend, diminish, or explain away the mistake can do more damage than the mistake itself.

Owning it means resisting the urge to build your defense before you acknowledge what happened.

For me, during the zipper schedule debacle, that meant standing in front of the entire staff and saying four words: “Well, that didn’t work.”

In that moment, my staff didn’t need an explanation. They needed me to acknowledge what they were already experiencing. Owning the mistake didn’t mean the original decision had been careless or that every part of the work had been wrong. It simply meant I was willing to say, without defending myself first, “This isn’t working, and I see it too.”

Step 2: Apologize For It

Saying “I’m sorry” can feel vulnerable, especially when our intent was never to cause harm. But intent and impact aren’t always the same thing, and a meaningful apology requires us to pay attention to both. The strongest apologies aren’t explanations disguised as apologies; they make space for the other person’s experience.

Years later, the teachers who remembered the zipper schedule weren’t talking about the hours I spent building the schedule or even all the ways it went wrong. They remembered that I stood in front of them, acknowledged what had happened, and didn’t pretend it was something other than what it was.

There are plenty of things I hope people remember from my years at that school. A failed master schedule probably wouldn’t have made my preferred highlight reel. But learning how to own my impact—and apologize when I needed to—is a leadership lesson I’m proud to have learned alongside some pretty incredible people.

Step 3: Learn From It

Owning a mistake and apologizing for its impact matter, but eventually we have to ask a different question: What can this teach me?

For a long time, I was much better at replaying what went wrong than examining what I could learn from it. There is a difference between reflection and rumination. Reflection helps us move forward; rumination keeps us circling the same mistake.

In The Drip Effect, Jimmy Casas and I describe a simple way to move from rumination to refinement:

• Zoom in: Examine what happened and pay attention to the feedback.
• Zoom out: Reclaim the full picture. One failure does not erase everything that worked.
• Adjust: Decide what you will do differently, and make the next small move.

When I zoomed in on the zipper schedule, one of the clearest problems became obvious: Building a modified block schedule gets much more complicated when multigrade classes land in the middle of the day and have to work around multiple lunch schedules. What had looked workable on paper became far more complicated once 900 students were actually moving through it.

But that didn’t mean the entire idea needed to be thrown away.

When we zoomed out and adjusted the model, changing from the zipper structure to an A/B day made a significant difference. We kept parts of what we were trying to accomplish while changing the part that simply wasn’t working.

That is the difference between rumination and refinement. The goal of reflection isn’t to keep proving that we screwed something up. It’s to make sure we don’t waste what the mistake has to teach us.

Step 4: Let It Go

I stewed on that zipper schedule for more than five years.

I replayed what went wrong, what I should have seen sooner, and what I might have done differently. And looking back, I think carrying that failure for so long may have made me a little more cautious about innovating and trying something new.

That is one of the risks of holding on to our mistakes too tightly. Eventually, we can stop treating them as something that happened and start treating them as evidence about who we are.

“That idea failed” becomes “Maybe I’m not good at this,” or worse, “Maybe I shouldn’t try something that ambitious again.”

The conversation with those two teachers helped me realize something I had missed for years: They had already moved on from the failure I was still carrying. They remembered the schedule, yes, but they also remembered the response, the learning, and what happened afterward.

Sometimes the person least willing to forgive your mistakes is you.

Leaders spend so much energy trying not to fail. But maybe the goal isn’t perfection at all. Maybe it’s becoming the kind of leader who can respond with honesty, humility, curiosity, and courage when things go wrong.

People rarely remember our mistakes the way we do.

They remember how we responded.