The Day I Got Schooled by a Carton of Strawberries
...and learned that awkward is the price of becoming
I was standing in the checkout line at Fresh Market, holding a carton of strawberries like it was a live grenade. The person in front of me was still unloading their cart. There was exactly eighteen inches of conveyor-belt space left.
My brain went full Homeland Security.
Do I put the strawberries down now and risk looking impatient?
Do I wait and look indecisive?
Do I make eye contact with the cashier?
Do I smile at the stranger?
Do I pretend to be fascinated by the gum display?
I froze.
A grown man, former Fortune 50 executive, host of a podcast that just hit #1 in health worldwide, paralyzed by produce placement.
I felt my face get hot. I felt ridiculous. I felt… awkward.
And in that moment, I heard a voice in my head that sounded exactly like my 13-year-old self:
“Don’t mess this up. Everyone is watching.”
That night, I told the whole pathetic story to Henna Pryor, expecting her to laugh at me.
She didn’t laugh. She just smiled the way someone does when they’ve heard some version of this story a thousand times and still loves humanity anyway.
“Of course, you froze. That’s your brain doing its job: protecting your ego from looking stupid. The problem isn’t the awkwardness. The problem is we’ve been taught to treat awkwardness like a bug when it’s actually a feature.”
She didn’t say it like a coach. She said it like someone who had stood in her own grocery line a thousand times and finally understood the software update was in progress.
And something in me exhaled.
Awkwardness isn’t a sign that something’s wrong. It’s the sound of your identity stretching. Henna calls it “the tax on growth.”
Every time you try something new, speak up in a meeting, ask for help, set a boundary, share an idea, dance badly, love again, your brain rings the awkward alarm.
Not because you’re in danger. Because your ego might be. That feeling in your stomach? That heat in your face? That voice whispering “everyone will think you’re an idiot”?
That’s the cover charge for becoming.
We’ve been sold the myth that confidence comes first, then action.
That one day we’ll wake up feeling ready, and then we’ll finally do the thing.
It’s backwards.
Confidence is not the prerequisite. Confidence is the receipt. You earn it by paying the awkward tax over and over until the alarm stops going off.
Henna told me a story that I think many of us can relate to.
Early in her career, she was the only woman, the youngest person, and the least experienced in a room full of senior executives. She had an idea that could have saved the company millions. She stayed silent for the entire meeting because she could feel the idea dying inside her mouth.
Afterward, she beat herself up for days. Then she made a promise: next time she would speak, no matter what. The next meeting came. She opened her mouth, and her voice cracked on the first syllable. She turned beet red. She stumbled through the idea anyway.
And the room listened. The idea was adopted. And something shifted inside her forever. That was the day she realized awkward isn’t the opposite of confidence. Awkward is the pathway to it.
I’ve been carrying that story around like a secret ever since.
Because I know exactly what it feels like to let the moment pass. To swallow the idea. To choose safety over self-expression. To watch the person I could have become stay trapped behind the person I was afraid to embarrass.
And I also know what it feels like on the other side of the awkward moment; when you do the thing anyway, and the world doesn’t end, when you survive the cringe and come out taller.
That’s where real confidence is forged. Not in the absence of fear. In the presence of action.
Episode 701 with Henna is 50 minutes of me trying (and mostly failing) to hide how much her message was rewiring me in real time. But the line that’s been living rent-free in my head since we stopped recording is this:
“Awkward is just your future self trying to break in.”
Every time you feel that spike of acute, visceral discomfort: that flush of heat, that urge to revert to tactical invisibility, it is not an ego defense.
It is the signal of a breakthrough. The sound of your identity stretching against its current limits. Your future identity is on the other side of that friction, demanding an upgrade to your operating code.
The decision is an executive choice: You can hit the abort button and remain defined by your current capability. Or you can execute the awkward action, accept the brief system failure, and push the upgrade through.
I’m done letting the signal override the mission.
My required action for the week: publishing this post while the thermal peak from that grocery-store moment is still active.
Your turn. What is the necessary, high-friction action you’ve been avoiding because you’re waiting for the signal to greenlight the risk?
Hit reply and tell me. I’ll read every single one, and I’ll be right there in the discomfort with you. Because the truth is, we’re not becoming despite the awkward moments. We’re becoming because of them.
→ Listen to the full conversation with Henna Pryor
Episode 701 — How to Get Good at Being Awkward (and Why It’s the Fastest Path to Confidence)
Download HERE, the Free companion workbook (micro-courage challenges + reflection prompts)