The great jazz trumpeter Miles Davis once said, “Sometimes you have to play a long time to be able to play like yourself.” This is why the best artists are not only masterful at their craft but also distinctive in their voice; they’ve committed themselves to the process of being themselves. Subsequently, this means they committed themselves to the failure that comes along with it also. But that’s the part no one talks about—the work required to “become” who we are or, better yet, who we want to be. It’s as if we’re expected to go to the gym and walk out with a six-pack. That’s not how the gym works, nor is it how work works. And we know this. There’s a process to becoming, and that process inherently requires failure.
Be that as it may, there are no LinkedIn claps reserved for failing. There are no at-a-boys for coming up short, despite the reality that we’ve all experienced failure to get to where we are. But of course, failure is just a natural part of the process of becoming. So why do we omit this truth from our stories when we tell the tale of becoming ourselves? Why do we whitewash the parts that aren’t so flattering and “yada yada yada” our narratives to a flatten expression of self. I get the fact that no one wants to fail, let alone admit to it. However, I also realize that in order to get good at something, we have to work through being not so good first. So, maybe we should practice sharing the entire story more frequently to help folks more successfully navigate this process of becoming. That’s exactly why we invited Courtnee LeClaire onto the FOR THE CULTURE podcast. LeClaire’s career trajectory consists of a who’s-who of brands. She was the head of worldwide app marketing and corporate partnerships at Apple after launching the iPod and iPhone. She’s held executive marketing seats at Disney and Intel before serving as CMO of the Oakland Raiders. But these days, LeClaire boasts a different title. Today, she is a chief “becoming” officer, an executive coach that helps leaders become their best selves, who they truly are, to help them achieve what Paul Coelho’s The Alchemist would call their personal legend. Despite her long list of impressive accomplishments, in this new role LeClaire spends more time talking about her failures, but she makes a pointed distinction between “failure” and “failing” that unlocks many of the challenges we have with failure.
{“blockType”:”mv-promo-block”,”data”:{“imageDesktopUrl”:”https:\/\/images.fastcompany.com\/image\/upload\/f_webp,q_auto,c_fit\/wp-cms-2\/2026\/01\/studio_16-9.jpg”,”imageMobileUrl”:”https:\/\/images.fastcompany.com\/image\/upload\/f_webp,q_auto,c_fit\/wp-cms-2\/2026\/01\/studio_square_thumbnail.jpg”,”eyebrow”:””,”headline”:”FROM THE CULTURE”,”dek”:”FROM THE CULTURE is a podcast that explores the inner workings of organizational culture that enable companies to thrive, teams to win, and brands to succeed. If culture eats strategy for breakfast, then this is the most important conversation in business that you aren’t having.”,”subhed”:””,”description”:””,”ctaText”:”Listen”,”ctaUrl”:”https:\/\/www.youtube.com\/playlist?list=PLvojPSJ6Iy0T4VojdtGsZ8Q4eAJ6mzr2h”,”theme”:{“bg”:”#2b2d30″,”text”:”#ffffff”,”eyebrow”:”#9aa2aa”,”subhed”:”#ffffff”,”buttonBg”:”#3b3f46″,”buttonHoverBg”:”#3b3f46″,”buttonText”:”#ffffff”},”imageDesktopId”:91470870,”imageMobileId”:91470866,”shareable”:false,”slug”:””,”wpCssClasses”:””}}
Failure, as LeClaire bifurcates, is a complete sentence. It’s done, and, therefore, it occupies real estate in our lives like a title—I failed, so I’m a failure. Failing, on the other hand, is an active sentence, meaning that there’s something that comes after it. And it’s the something that comes after it that enables us to do something about it. I’m failing, so I need to [fill the blank]. I was failing, so I [fill in a blank some action].
The reframing of failure to failing is what opens the door for success. Whether it’s something new or something new to us, there will be a point when we are failing relative to our ambition and taste. But when we perceive it as an active sentence, we give ourselves room to improve. Failure is something we experience, not who we are. It’s a moment in time, and because it’s something we’re merely experiencing, that means we can change it. This distinction is critical. One is a state of who we are (failure), and the other is a state of where we are (failing). When we reposition failure to failing (or I was failing), we acknowledge the reality of where we are relative to where we want to be and can now honor the fact that this is just a part of the process.
To hear this from LeClaire during our conversation on the pod had a profound impact on me personally because I worked with her during my time at Apple. She was much more senior than I was, and I “totemized” her as the consummate example of having it all together. She wasn’t in my reporting vertical, but I got to engage her from time to time, where she’d drop marketing wisdom and sage advice for how to navigate life on One Infinite Loop. To hear her reveal her moments of failing on her way to becoming, even in those moments when I held her on a pedestal, was like learning that Spiderman is really Peter Parker. That is to say, LeClaire, like all of us, had to play a lot to learn to play like herself. Fancy that.
Hearing this not only humanized LeClaire but also gave me permission to admit to my own failings and accept the fact that we’re all just buffering, even the best of us, as we become our best selves. Imagine how empowering that would be if we all started to share our own processes of becoming, moving from failure to failing; it might help us all navigate the process with a bit more grace—and perhaps even a bit more success.
Check out the full episode of our conversation with Courtnee LeClaire on the latest episode of the FOR THE CULTURE podcast on Spotify or wherever you get your podcast.
{“blockType”:”mv-promo-block”,”data”:{“imageDesktopUrl”:”https:\/\/images.fastcompany.com\/image\/upload\/f_webp,q_auto,c_fit\/wp-cms-2\/2026\/01\/studio_16-9.jpg”,”imageMobileUrl”:”https:\/\/images.fastcompany.com\/image\/upload\/f_webp,q_auto,c_fit\/wp-cms-2\/2026\/01\/studio_square_thumbnail.jpg”,”eyebrow”:””,”headline”:”FROM THE CULTURE”,”dek”:”FROM THE CULTURE is a podcast that explores the inner workings of organizational culture that enable companies to thrive, teams to win, and brands to succeed. If culture eats strategy for breakfast, then this is the most important conversation in business that you aren’t having.”,”subhed”:””,”description”:””,”ctaText”:”Listen”,”ctaUrl”:”https:\/\/www.youtube.com\/playlist?list=PLvojPSJ6Iy0T4VojdtGsZ8Q4eAJ6mzr2h”,”theme”:{“bg”:”#2b2d30″,”text”:”#ffffff”,”eyebrow”:”#9aa2aa”,”subhed”:”#ffffff”,”buttonBg”:”#3b3f46″,”buttonHoverBg”:”#3b3f46″,”buttonText”:”#ffffff”},”imageDesktopId”:91470870,”imageMobileId”:91470866,”shareable”:false,”slug”:””,”wpCssClasses”:””}}
