Why cringe is the bridge to confidence


Enneagram Five Newsletter

Issue #014

Why cringe is the bridge to confidence

Recently, I shared with you how everything in me wanted to skip my first kickball game.

New people, loud bar, unfamiliar activity, and my nervous system said nope. But, I went anyway.

What I didn’t tell you is what happened next.

Each week, the same pattern played out: I’d show up, fumble through, and leave feeling a bit awkward and unsure. I’d second-guess how I acted, what I said, whether I fit in at all. And every week, my brain gave me a fresh reason to opt out.

But I kept going. I didn’t wait to feel confident. I just let it be cringey and did it anyway.

Last night, something unexpected happened.

I actually enjoyed myself.

I wasn’t performing. I wasn’t analyzing. I was just… there. Present. Laughing. Connected. The discomfort didn’t vanish, but I also wasn’t ruled by it.

This, I’ve come to realize, is how confidence works for Fives.

The real reason momentum is hard

Last night's lesson was all about this moment.

Because for Fives, the hardest part of growth often isn’t starting, it’s staying in motion.

You say something vulnerable. You take a bold step. You show up.

And then your brain slams on the brakes:
“Was that dumb?”
“I shouldn’t have said that.”
“Maybe I need to rethink all this.”

We call it the recoil. It's that wave of mental discomfort that hits right after you act.

It doesn’t sound like panic. It sounds like logic. But, it’s fear in disguise.

And if we don’t catch it, we retreat. Again.

Cringe ≠ failure

The recoil isn’t a problem to solve. It’s a signal that you’re growing.

The goal isn’t to eliminate it. It’s to build tolerance for it.

Which brings us to the simplest, strangest, most powerful mantra I’ve found:

Let it be cringey.

Say it out loud. Say it in a ridiculous voice. Say it when your brain begs you to backpedal or rewrite the email or ghost the group chat. Say it when you feel exposed, awkward, or unsure.

Let it be cringey and take one more step.

Because every time you stay in motion, you’re retraining your nervous system. You’re proving to yourself that you can feel discomfort… and keep going.

Your turn

What’s one thing you’ve already taken a small step toward something that matters to you, but feels awkward or uncomfortable to keep doing?

This week, take just one more step. Nothing huge. Just a small, deliberate move. Then pause. Breathe. And say it:

Let it be cringey.

You’ve got this.

Josiah Goff

Say hi 👋🏻 on Instagram, Threads, or LinkedIn

Whenever you're ready, here are some ways to go deeper:

Join the Five Community (Free) – Connect with other Fives on the same path. Join here

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