When creating something new feels awkward, do it anyway
Especially when your inner critic is breathing down your neck about doing it “right”.
Yep. I know. But just try it anyway.
Let’s get real: Awkwardness is part of the process
You want to try something new. You’re drawn to it. Maybe it’s writing, painting, playing with design tools, starting a blog, or finally opening that Canva account everyone’s talking about.
But instead of doing the thing, you… organize your sock drawer. Or scroll. Or stare at it.
Why?
Because new things feel awkward, and somewhere deep down, you’ve learned to treat that awkwardness as a warning sign.
“You don’t know what you’re doing.”
“This is going to look bad.”
“People will think you’re trying too hard.”
Sound familiar?
Yeah. That’s Barbara.
Meet Barbara: your inner perfectionist with big opinions
Barbara is the voice that panics when you don’t know what you’re doing.
She hates mess. She loves control. And she deeply believes that if you can’t do something well, you shouldn’t do it at all.
(I disagree.)
Barbara shows up right when you’re about to do something new. And awkward. And exciting.
She’s trying to protect you, sure. But also? She’s kind of a buzzkill.
Client story: “I almost quit before I even started.”
One of my clients (we’ll call her Jenna) wanted to try art journaling.
She bought a journal. Set up her space. Picked a time. Then spent 30 minutes staring at the first page.
Her words:
“I was suddenly paralyzed. I felt ridiculous. Like... who do I think I am? An artist?”
Barbara was thriving.
We talked it through. I gave her one job: Rip the first page out. Start with the second. Make a mess. Scribble something dumb. Use a color she doesn’t even like.
She did it. And a week later? She had six messy, beautiful, totally imperfect pages and zero regrets.
That awkward beginning wasn’t failure. It was the start of trust.
My story: “It was giving accidental 80s web design.”
I’ve rebuilt my website so many times, I’ve lost count. And let me tell you, the early versions? Yikes.
My first attempt looked like a cross between a high school slideshow and a motivational poster from 1987. It had clashing fonts, buttons that went nowhere, and colors that didn’t match anything except maybe a pair of leg warmers.
It didn’t match my voice, my brand, or my vision, and I knew it.
But I kept showing up. I tweaked. I messed up. I learned. I redesigned again.
And over time, I created something that actually felt like me.
Not because I got it right on the first try, but because I let myself be awkward and kept going.
Read: How creative expression improves your mental health
Mind shift tips: When awkwardness shows up, try this
✦ Awkwardness means it matters
If it didn’t matter, you wouldn’t feel vulnerable doing it. Awkwardness is often a sign you care and that you're entering a growth zone.
Barbara’s take: “Let’s care less and stay in our comfort zone forever.”
Our take: “Nice try, Barb. We’re growing.”
✦ Stop aiming for graceful and aim for real
Nobody looks cool their first time out. The goal isn’t to glide through it like you’ve done it for years. The goal is to show up and try.
That’s where momentum comes from.
✦ Confidence doesn’t come first
We’ve been sold a lie: that people become confident before they take action. In truth, confidence is what you get after doing something awkward enough times that it stops feeling scary.
Confidence is a side effect of showing up, not a prerequisite.
✦ Get curious about what awkwardness is covering
Sometimes awkwardness is just resistance in disguise. And sometimes? It’s fear of judgment—yours or someone else’s.
Name it. Get curious. Ask:
“What’s Barbara trying to protect me from here?”
And then gently remind her that you’ve got this.
✦ Plan to feel awkward and celebrate it
Make awkwardness the goal. Seriously.
Try this reframe:
“I’m going to do something badly and be proud of myself for doing it anyway.”
Every time you follow through, Barbara gets a little quieter. And your creative self gets a little louder.
Read: How to make space in your week to experiment with creativity
Ready to show up, even if it’s messy?
You don’t need to feel ready. You don’t need to have it figured out. You just need to be willing to feel awkward for a minute longer than usual.
Tell us what you’re going to try, even if it feels awkward. Drop it in the comments.
New around here? Welcome.
At Intendify, we break life down into 12 key areas and offer guided paths to help you reflect, plan, and take action—so you can start living more intentionally, one step at a time.
It’s like having a life coach in your pocket, minus the awkward eye contact.
The Creativity life area can help you reconnect, experiment, and make space for joy. No talent or big projects required.