Back from an inspiring trip to ShopTalk - where I connected with peers, learned from some of the brightest minds in retail, and was reminded why this work still excites me. I’m now sitting on the back porch with a latte. The sun is rising, and I’m reflecting. Not just on the week that was but on the week ahead. And in this quiet moment, I keep returning to one idea: that imperfection is where the real beauty lives.
I used to chase perfection. Clean lines. Crisp words. Perfect outcomes. Oh, who am I kidding - I am still guilty of it.
Anyone who has worked with me on a presentation knows: I can’t help myself. I’ll say, “Don't be concerned with the format,” but then I’ll quietly realign every font box, square off a rogue image, and make sure that every graphic is crisp and high-resolution. I won't always admit it out loud, but I’m always striving for that final layer of polish.
This past week, a friend of mine interviewed me for his podcast. He asked one of those familiar-yet-thought-provoking questions: “What advice would you give your younger self?”
I answered quickly - maybe too quickly - and defaulted to the all-too-common, well-meaning refrain: “Don’t be afraid to fail.” And sure, it’s not bad advice. In the early stages of my career, I was hyper-focused on not messing up. I’ve often told others that failure doesn’t define you - it teaches you.
But later that day, I found myself reflecting. If I had the chance to revise my answer, I’d say this instead:
Don’t just stop fearing failure - start embracing imperfection.
And I say that with full awareness of the growing conversation around AI and the perfection it seems to promise. We worry that AI might take our jobs - or worse, erase the human element - because it can execute flawlessly. But here’s the thing:
Perfect isn’t always beautiful. Imperfect often is.
Somewhere between version 4.08 and 4.09, I realized something:
The magic lives in the imperfect take - the unexpected wrinkle, the missed stitch, the idea that felt just a little too raw to publish.
Whether it was a conversation with a friend stuck in draft mode, a suit tailored by Martin Greenfield that was purposefully imperfect, or watching AI models try (and fail) to predict the unpredictable - there’s a pattern:
Our flaws tell our story. Our imperfections make us memorable.
In a world obsessed with optimization, what if our power comes not from flawless execution - but from the courage to try, reflect, and try again?
The Myth of Flawless
We live in a results-driven world, and perfection gets a lot of praise. We love polished endings. We share the highlight reels. But what we don’t see is all the messy middle - the nights we second-guessed ourselves, the half-baked drafts, the times we stopped before we started.
A friend recently told me they couldn’t finish a piece of writing because they wanted it to be "just right." But in trying to make it perfect, they made it impossible. That fear of a flaw can be more paralyzing than failure itself.
Perfectionism isn’t precision - it’s procrastination in a pretty outfit.
Kintsugi Thinking
If you’ve read any of my previous posts or articles, you probably know I have a deep appreciation for Japanese culture. In particular, I'm drawn to concepts like wabi-sabi (the beauty of things imperfect and incomplete) and kintsugi (the art of repairing broken pottery with gold).
I won’t overplay it here - but there’s something powerful in the idea that the break isn’t something to hide; it’s something to highlight. Not just fixing the crack, but honoring it. Letting the damage become part of the design.
What if we approached leadership, creativity, and life like that?
Kintsugi doesn’t say, “This was broken.” It says, “This was lived in. This has a story.”
We’re drawn to things that carry a history - whether it’s a worn leather chair, a vintage record with a scratch, or a brand that’s candid about its journey. It’s the golden cracks that connect us.
A Master Tailor's Imperfect Stitch
Years ago, I had the opportunity to work with Martin Greenfield. If you don’t know who he is, take a moment to Google him - or better yet, do a bit of "deep research". He was a Holocaust survivor who came to this country with nothing. Through resilience and relentless work ethic, he bought the very factory he once worked in and built Martin Greenfield Clothiers in Brooklyn, where suits were made by hand by master tailors. He wardrobed presidents, athletes, and movie stars.
I was a product director for Brooks Brothers then. During an inspection of an order of suits he had made for us, I noticed some details that didn’t look quite right - one in particular was buttonholes that seemed, well, less than ideal.
So I brought it up. Not too kindly, either. I suggested he might want to consider using an automated buttonhole machine - the ones we used elsewhere looked “better.” He was upset. He looked me in the eye and said, “Would you ask an artist to sign a work of art with an autopen?”
I didn’t have a good answer. He continued: “Tell me that my buttonholes don’t look great, and I’ll work with the tailor on how to do it better. But don’t ever ask me to sign my work with an autopen!”
It hit me.
Yes, the buttonhole could be corrected. But it would have been a mistake to strip it of the slightly imperfect signature of the person who made it. It was their mark. Their humanity.
And ever since then, I’ve seen things a little differently.
AI Can’t Predict Magic
We work with a lot of smart systems. AI tools that scan data, write headlines, and even try to predict what a customer will do next.
But here’s the catch: they can predict patterns, not passion. They can optimize, but they can’t feel.
As a real-time example: I used several AI platforms this year to help predict my March Madness bracket. In some cases, they correctly picked a few upsets. In others, not so much. I’m tracking about average in my pool.
Sure, AI will get more sophisticated. It will likely predict outcomes with greater and greater accuracy. But it still won’t know who’s having a good day or a bad one. Who walked into the gym with quiet confidence - and who’s carrying the weight of self-doubt. It won’t understand which team might unexpectedly gel in a moment of momentum, and which one might collapse under pressure.
And that’s the difference. That’s the humanity. That’s where we not only survive - but where we thrive.
Some of the most groundbreaking ideas weren’t born from perfect logic but from instinct, emotion, or risk. And risk is inherently imperfect.
Imperfection isn’t a failure of the system. It’s a feature of the human spirit.
From Fear to Curiosity
We often tell people to embrace failure. And that’s not bad advice - it encourages risk-taking and bravery. But it can also be misunderstood. We’re not telling people to aim for failure.
What we really mean is: take the shot. Even if it’s not perfect. Even if you’re unsure.
Sometimes the most important move isn’t avoiding failure, but simply starting anyway.
When we stop fearing imperfection, we start inviting curiosity. And curiosity leads to experimentation, discovery, growth.
In teams I’ve led, the shift from "don’t mess up" to "try something new" changed everything. People leaned in. They asked questions. They built things that had never existed before.
The safest path might avoid mistakes, but it also avoids magic.
If we want to be bold, we have to be brave enough to be imperfect.
Closing Thought: Maybe 408 Was Enough
We always hear about Formula 409 - the household cleaner named after its 409th iteration. Maybe 408 would have been good enough. Maybe they were absolutely right to keep pushing for perfection.
But here’s the thing: we can’t let the pursuit of perfection stop us from making progress. From creating something real. From putting our name on something and saying, “This matters - even if it’s not flawless.”
Because the anxiety around failure, success, perfection, and risk? That’s real. It lives in all of us.
This piece isn’t labeled under "The Sunday Scaries", but it could have been. Because perfectionism and the fear of not getting it right often show up right there - with our doubts, our what-ifs, and our internal critics.
So if I could revise what I said in that podcast interview one more time, here’s what I’d say:
Don’t just avoid fearing failure - start embracing imperfection.
In your projects. In your work. In your job. In your relationships and your friendships.
Perfect is predictable. Perfect is boring.
Imperfection is beautiful.
And humanity? Humanity will always be imperfect.
And maybe that’s the most powerful thing about us.
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