In The Mistakes That Make Us: Cultivating a Culture of Learning and Innovation, I wrote that
“mistakes are inevitable, but failure is not.”
The real differentiator is how we respond to mistakes—not just as individuals, but as organizations. Do we hide them? Punish them? Or do we learn, iterate, and sometimes discover something even better?
That mindset shift is at the heart of building a culture of continuous improvement and innovation. And it’s exactly what played out—quite literally—in the warehouses of the well-known Woodford Reserve distillery, which makes the official Bourbon of the Kentucky Derby.
Mistake #1: Aged Too Long… and Better Than Ever
Woodford Reserve’s Double Double Oaked Bourbon wasn’t supposed to happen. It emerged when a batch of their regular Double Oaked Bourbon spent longer than planned in its second barrel—a heavily toasted, lightly charred oak cask. The company’s standard process is said to call for a 7-month (or so) secondary maturation. These barrels went longer. A lot longer.
From a technical perspective, the whiskey was “out of spec.” That could have meant discarding it or trying to blend it away. Nah. What a waste that would be!
Instead, the team got curious. They tasted it. And what they found surprised them: rich notes of butterscotch, cherry, toasted almond, orange creamsicle, even a hint of bubblegum nostalgia (or so the experts say).
That wasn’t a mistake to cover up. It was a mistake to repeat—on purpose. Today, Double Double Oaked is a nationally available product, retailing for $200 a bottle. What started as a tracking error became a flagship offering that’s very hard to get.
Mistake #2: The Toasted Bourbon That Wasn’t Supposed to Be
The story gets better.
Another limited-edition expression—Toasted Bourbon—was born from a barrel mix-up. A shipment of specialty barrels intended for finishing Double Oaked Bourbon (again, toasted and lightly charred) was mistakenly filled with new make spirit. That’s not how the process was supposed to work.
But instead of dumping the contents or chalking it up to a logistical error, the distillers once again said, “Let’s see what happens.”
What happened was worth bottling.
Distillers don’t like to waste anything they’ve distilled. And for good reason!
Why These Stories Matter (Beyond the Bourbon)
What stands out in both cases isn’t just the happy accident—it’s the culture that allowed the mistake to become something more. At Woodford Reserve, leaders apparently didn’t react with blame or other behaviors that would cause fear. They seem to have responded with curiosity, with experimentation, with learning.
As I emphasize in The Mistakes That Make Us, when people feel psychologically safe, they’re more willing to speak up, own up, and explore the unexpected. That’s how we get innovation—not from perfection, but from possibility.
Chris Morris, Woodford’s master distiller emeritus, explained that they’ve even experimented with going beyond the “Double Double” into longer finishes. But they’ve learned where the peak is—and where the oak begins to dominate (where it’s too oaky). That’s another form of learning from mistakes: finding the edges of excellence.
Elizabeth McCall, the current master distiller, added, “It’s also fun to be able to hold onto something and see what happens.” That phrase encapsulates the essence of an improvement culture—one where patience, experimentation, and trust lead to better outcomes than rigid control ever could.
The Takeaway for Leaders (and Bourbon Fans)
You don’t have to run a distillery to learn from these examples. In healthcare, manufacturing, tech, or any other sector, we all face moments when something veers off course. The question is: Do we have the culture and the curiosity to pause, taste, and ask, “What might this become?”
Mistakes are going to happen. But as Woodford Reserve shows, some mistakes are worth repeating—and worth celebrating.
So next time you’re sipping a glass of Double Double Oaked, raise it to the barrels they lost track of… and to the leaders who knew what to do when they found them again.
If you enjoyed this story and want to explore more examples of how mistakes can drive learning, innovation, and long-term success, check out my book, The Mistakes That Make Us: Cultivating a Culture of Learning and Innovation.
It’s filled with real stories—from Bourbon to boardrooms—that show how embracing mistakes can lead to breakthrough results.
👉 Learn more and order your copy at MistakesBook.com
Or subscribe to the My Favorite Mistake podcast to hear how leaders, creators, and changemakers are turning missteps into momentum.
