Messy Moves, Mismatched Shoes & the Confidence That Chaos Built
- Caroline Esterson
- Jul 22
- 3 min read
Because progress isn’t tidy, it’s scrappy, brave, and surprisingly effective.
Let’s start here: I once turned up to a client research day wearing one black shoe and one blue. This was not a style statement. It was the result of a whiskey-fuelled detour, a missed flight, and a desperate overnight stay in my car at Stansted Airport. I was young, eager, and didn't really think through the consequences of my actions.
But I showed up. Slightly lopsided and 100% committed. And we still won a big contract.
Not because I had it all together, not because I nailed every bullet point, but because I showed up, was really present and noticed the little things. I did it anyway, despite the poor shoe choice and made sureI added value.
That experience (and about fifteen others like it) taught me a truth I now live and coach by:
👉 Messy action gets results.
The Myth of Perfection
We’ve all been seduced by the idea of getting it “right” before we make a move.The perfect CV. The polished LinkedIn post. The beautifully colour-coded plan that gets stuck on page one of a Notion board and never sees the light of day again.
But perfection is often just fear in disguise. We call it planning. We call it preparation. But really? We’re avoiding - avoiding the cringe/ the wobble/ the feeling of not being “ready.”
The problem is: waiting rarely builds confidence.
Action does.
Reps > Readiness
Earlier this week, something massive happened. My son had his passport stolen on the way to the airport. He was alone, in a different country, and he has autism, so uncertainty doesn’t just rattle him, it completely dysregulates him.
And yet… he handled it. We handled it.
Not because either of us is naturally chill, cool-headed logistics ninjas.(If you know me, you know that’s not the vibe.)
We got through it because of reps. Small, scrappy moments (over years) that built the muscle for handling chaos and gave us confidence that we'd got this. Confidence doesn’t arrive fully formed. It’s built in the mess.
Brené Was Right
Brené Brown says:
“There is no courage without vulnerability. Vulnerability is not weakness. It’s the ability to show up and be seen when you can’t control the outcome.”
That’s what messy moves are—micro-moments of courage, tiny acts of “I’ll try it anyway.” Sometimes, they result in wins, sometimes in wild embarrassment, but always in growth.
The Career Advice No One Gives You
One of my favourite quotes from the Little Moves, Big Careers interviews came from Jon Turner. He said:
“You can’t possibly expect everything to be perfect when you’ve got less than 10 years’ experience. Go make the mistakes.”
YES. Say it louder for the spreadsheet perfectionists and permission seekers at the back.
You’re not supposed to have it all figured out.You’re supposed to try.Test.Trip up. And learn faster because of it.
The Podcast Episode That Goes Deeper
In this week’s episode of the Little Moves, Big Careers podcast, I take you behind the scenes of some of my most mortifying, magic-building moments, including:
The time I hit “Reply All” with a snarky comment to 200 people (yep, including the Director)
The coffee-covered pitch moment where we looked like a health & safety hazard… and still won the contract
And why the first draft (of anything) is more powerful than perfection
Want to Build Your Own Reps?
Download the free Messy Moves Tracker - your permission slip to start small, show up scrappy, and make progress the human way. It’s zero-pressure. Zero fluff. And 100% built to help you move.
Final Thought
You’re not faking it. You’re learning it. Every bold career was built on awkward first drafts, uncomfortable experiments, and unpolished, repeated action.
So if you’re waiting to feel ready? Don’t.
Do it anyway. Even if it’s messy.Especially if it’s messy.
🌀 If this blog hit a nerve, send it to someone else who's sitting on the edge of a brave move. Or better yet, share your own messy moment with me. I’m collecting them for the official Wall of Beautiful Chaos.
Comments