First Day Thoughts: How to Turn a Mistake into a “Beautiful Oops”

During this morning’s opening Middle School Convocation, I shared this reflection with our students.

Everyone in this room is going to experience moments of success this year. You will learn new skills, compete on the playing field, perform on the stage, and adventure in the great outdoors.

And, undoubtedly, you will also have moments where you struggle. We will all make a lot of mistakes. But let me tell you a secret: if you look closely, you might discover that your successes, your struggles, and your mistakes walk hand-in-hand. Sometimes, our greatest triumphs emerge from our biggest challenges.

I want to tell you a few stories to explain what I mean by this. My five-year-old daughter loves to paint, but the picture she has in her mind does not always translate exactly to the page.  Does that sound familiar? It does for me! For example, this weekend she took on an ambitious painting project. She wanted to create a mermaid . . . dancing with an octopus  . . . in an underwater castle . . . that was built out of chocolate and lollipops.

Yeah, not the easiest image to paint for someone just entering Kindergarten.

She was feeling pretty good, until she got to that octopus. When she realized that she had painted nine legs instead of eight, her face crumpled. Have you ever had a moment like that –  when you were working on a project or a design, and it just didn’t turn out the way you imagined?

At our house, we have a phrase for such moments: “See if you can turn a mistake into a beautiful oops.” Perhaps, as my daughter discovered, with a little extra paint that nine-legged octopus could be transformed into an octopus playing a jazzy saxophone. With a little courage and creativity, she turned a mistake into an opportunity, and she created new possibilities for herself . . . and for that octopus.

The phrase “beautiful oops” comes from a picture book by the same name by Barney Saltzberg. Let’s take a look:

We all face challenges. We all get frustrated. And sometimes we don’t know what to do next. But I think the lesson that this story teaches is that mistakes are not an end –  they can be bridges to amazing possibilities and can open up new ways of thinking.

In 1928, a British scientist named Alexander Fleming locked up his lab and went on summer vacation with his family.

When he returned to his lab a few weeks later, he made a disheartening discovery: he had forgotten to sterilize his petri dishes before he left, and they were covered with bacteria and mold. 


So he set to work cleaning up his mess.  

As he cleaned, he noticed something peculiar: there were rings around the mold colonies that were completely free of bacteria.  Something about that mold was destroying the surrounding bacteria. That day, in that messy lab, Fleming discovered penicillin –  the first true antibiotic. This accidental discovery –  this beautiful oops — has saved millions of lives.

Can you imagine what he was thinking when he got back after vacation: “Ugh, I can’t believe I forgot to clean before I left.  Now my petri dishes are a disgusting mess!”  But he did something essential when it comes to learning from mistakes: He kept his eyes open.  He noticed the little things. In the mess, he saw possibility.

What would happen if we all trained ourselves to see possibility in our messes and mistakes? I recently heard an interview with Sara Blakely, a successful entrepreneur.  According to Blakely, the best piece of business advice she ever received came from her father.  She said:

When I was growing up, he encouraged us to fail. We’d come home from school and at dinner he’d say: ‘What did you fail at today?’ And if there was nothing, he’d be disappointed. It was a really interesting kind of reverse psychology. I would come home and say, “I tried out for something and I was just horrible,” and he high-fived me. A lot of entrepreneurs are held back from the fear of failure, so that lesson from my dad was a real gift . . . Failure is not the outcome; failure is not trying.

Think about the Olympians that we cheered for this month. We saw most of them at their best.  We didn’t see all the work it took to get there. During her years of training, how many times did Simone Biles fall down as she practiced her gravity-defying flips? How many average-speed laps did Katie Ledecky swim as a child before she developed the strength and skills to shatter world records? I also think about all the athletes who didn’t win a medal but whose dedication inspires millions to try a little harder at whatever passion they feel called to pursue.

Each year, in this opening convocation, I issue one challenge, “Leave a place better than you found it.” There are obvious ways to do this: Offer a kind word to a classmate. Thank a teacher.  Pick up the trash you see in the hallway.  But this year, let’s expand our understanding of this motto. Let’s look for ways to transform mistakes into opportunities for enriching ourselves and others. Let’s embrace each moment –  even those that are frustrating or challenging – and open ourselves to possibilities. Let’s remember that there is beauty in every “oops.” If you look at the world this way, who knows what you may discover? Who knows where it might lead you?

*Image from Barney Saltzberg’s Beautiful Oops.




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