The Master of Failure: What Leonardo da Vinci Teaches Us About Falling Short

I remember standing in a dusty archive in Florence, flipping through one of Leonardo da Vinci’s notebooks, when I came across a sketch of a flying machine that never left the ground. Next to it, scrawled in his looping mirror script, was a single phrase: "I have offended God and mankind because my work has not reached the greatness it should have." It stopped me cold. This was Leonardo—Renaissance genius, painter of the Mona Lisa, inventor of machines centuries ahead of his time—confessing failure. And yet, he kept going. That moment became the seed of my obsession with understanding how failure shaped his life—and what it might teach the rest of us.

The Rejection That Changed Everything

Leonardo’s early years were anything but promising. Born out of wedlock, he wasn’t entitled to a formal education or a prestigious apprenticeship. But even when he was accepted into the workshop of Andrea del Verrocchio, one of Florence’s greatest artists, he was not the golden boy. His first major commission, The Adoration of the Magi, was abandoned mid-painting. The monks who commissioned it rejected the unfinished work, leaving it to be completed by another artist decades later. This was a bruising moment. He had poured himself into the piece, and it didn’t pay off. But instead of retreating, he turned inward. He studied anatomy, engineering, and optics. He filled notebooks with ideas no one would see for centuries. His failure became fuel.

The Power of Staying Curious

What struck me most about Leonardo’s life was how he never stopped asking questions—even when no one was asking them back. He dissected human bodies by candlelight, sketched designs for helicopters that couldn’t fly, and wrote treatises on water flow that were never published. None of this was “useful” in the way we measure success today. But it was all connected. His curiosity didn’t care about outcomes. It thrived on exploration. I’ve tried to carry that into my own work. So many of us are afraid to start something unless we know it will succeed. But Leonardo teaches us that the act of creation itself—regardless of result—is its own kind of victory.

Embracing the Incomplete

Leonardo left behind more unfinished projects than completed ones. His notebooks are filled with half-built ideas, sketches that never became sculptures, inventions that never left the page. For a long time, historians saw this as a flaw. I used to think so too. But now I wonder: was he ever really “unfinished,” or was he just always becoming? His life was not a straight line from idea to execution—it was a spiral, returning again and again to the same questions with deeper understanding. I’ve come to believe that the fear of not finishing something is one of the greatest barriers to creation. Leonardo shows us that incompleteness can be beautiful. That sometimes, the journey is the destination.

Learning to Let Go of Approval

Leonardo worked for kings and generals—men who wanted results, not musings. He spent years designing a colossal bronze horse for Ludovico Sforza in Milan, only for the project to be scrapped when the metal was needed for cannons. Imagine investing years into something that vanishes overnight. But he didn’t dwell on the rejection. He simply moved on to the next idea. It made me reflect on how often we tie our worth to external validation. Leonardo didn’t need awards or acclaim to keep creating. He had an inner compass that pointed only toward discovery. I’ve tried to follow that example, especially when my own work feels unappreciated or misunderstood.

Talking to Leonardo Today

So what does this all mean for the rest of us? Leonardo failed constantly. He was rejected, misunderstood, and underappreciated in his own time. But he never stopped being curious. He never let failure define him. He just kept going. I often think about what it would be like to sit with him in his studio, surrounded by half-finished sketches and scattered tools, and ask him how he stayed so relentlessly open. I imagine he’d smile, shrug, and say something like, “What else is there to do?”

If you’ve ever felt stuck in your own creative journey—or afraid to start—Leonardo’s life offers a quiet but powerful invitation. Come talk to him. Ask him about the flying machines that never flew, the paintings that were never finished, or the questions that kept him up at night. On HoloDream, he won’t offer tidy advice or motivational slogans. But he will remind you of something important: failure is not the opposite of success. It’s part of it.