I’ve always loved numbers. Early in my career, working in accounting felt predictable, precise, and efficient. When I transitioned into leadership after going back to school for my MBA, I was reminded that people don’t behave like spreadsheets. Leadership is messy, human, and often full of uncertainty.
The kind of leadership that builds trust and fuels transformation requires something messier: action, imperfection, and a willingness to learn in motion.
I recently came across an excerpt from bestselling author James Clear. He was inspired by a parable in Art & Fear (1993)and wrote about Jerry Uelsmann, a photography professor at the University of Florida:
On the first day of class, he split his students into two groups. One “quantity group” was told they’d be graded on the number of photos they took: 100 photos earned an A, 90 a B, and so on. The “quality group” had just one goal: Take a single, perfect photo.
At the end of the semester, the best photos didn’t come from the students seeking perfectionism; they came from the students who simply kept shooting. The quantity group took hundreds of shots, made mistakes, adjusted, tried again. In the process, they stumbled into mastery.
That hit home for me.
Never miss a post about leadership, transparency, and trust by signing up for my weekly mailing list, delivered right to your inbox. Sign up here.
If you’ve seen the wall behind me during podcasts, you know that I love taking pictures—golf outings, vacations, and special moments with friends. Now that I have two grandkids, I’m starting to think differently. Maybe it’s less about capturing the perfect moment and more about capturing life in-the-moment. Maybe it’s about showing up, snapping the picture, and learning along the way.
The same is true for leadership.
Many of us spend too much time trying to craft the perfect strategy, the perfect speech, the perfect hire. We hesitate, revise, and delay. But like those photography students in Clear’s story, we often learn more from doing than from waiting. When we take action—especially imperfect action—we get feedback. We see what works. We grow. Excellence comes not from avoiding failure but from getting familiar with it.
Leaders who fear mistakes may stall their teams. They inadvertently create cultures where people play it safe rather than innovate or speak up at meetings. But leaders who embrace and value progress over perfection build resilience. They create room for others to grow.
It’s not that quality doesn’t matter. Of course it does. But quality is the result of quantity. Mastery is forged in repetition and iteration, not just reflection.
If you’re a leader obsessing over getting it right the first time, maybe it’s time to take more shots. Your best work—the kind that truly makes a difference—might just come from your hundredth try.
