The “radical overconfidence” challenge

“Radical overconfidence” is like stage makeup. If you’ve got enough makeup on to look good in the daylight, you’ll wash out completely onstage. To command the audience’s attention from the stage, you’ve got to exaggerate your features. Make your eyes pop with some false eyelashes. Redden up those lips.

Sara Benincasa practices radical overconfidence
Sara Benincasa, photo by Iconic Pinups

And so it is with radical overconfidence. Especially for women, what we identify as regular-strength confidence remains all but undetectable to other people (especially the male people). So slap on the metaphorical false eyelashes and learn how to be radically overconfident.

I first encountered the concept in Sara Benincasa‘s funny, practical, and poignant book Real Artists Have Day Jobs (And Other Awesome Things They Don’t Teach You in School).

Now, we’ve all seen people whose confidence far outpaces their abilities. (In fact, you may feel that such a person resides in a certain edifice—let’s describe it as a white house—in Washington.) No one wants to be that person. Well, no one with a modicum of self-awareness. As a result, many of us over-correct. Instead of radical overconfidence, we practice radical underconfidence.

The problem is, that doesn’t get us anywhere. Underconfidence keeps the brilliant woman manager from speaking up in a meeting; overconfidence keeps the arrogant men in the room from listening when she finally does. In the world of creativity, underconfidence keeps perfectly good writers from sharing their work even with a writing group—while overconfident writers pound out the book proposals and ink publishing deals. Or self-publish their poorly written drivel.

Radical overconfidence and you (…okay, and me too)

Benincasa writes about “radical overconfidence” in the context of walking into a meeting, perhaps a pitch meeting:

“What would happen if I engaged in radical overconfidence?….if I displayed chutzpah aplenty—the sass and strength that I imagine are the rightful possession of a richer, bolder, better-looking person? What would go down if I waltzed into that joint with my head high, my smile bright, my shoulders squared, and my heart brimming with the belief that I kick fucking ass?”

What indeed?

For Benincasa, radical overconfidence means advocating for herself:

“Rather than being sweet and unassuming, I had to be bold and brave. I could still be nice. I could still be kind. I could still celebrate other people’s achievements and glean wisdom and understanding from studying their feats….But enough of the meek shit….If I was to get what I wanted from life—or at least from the entertainment and publishing industries—I had to act like I owned it. I had to act like I was owed it by virtue of my sheer awesomeness. I had to display radical overconfidence.”

So here’s my challenge—to you and to myself. Let’s practice radical overconfidence. Start with one act of radical overconfidence a day, every day for a week. Just once a day, walk into a room like you own it. Hand something you’ve written to a trusted advisor and ask them to read it. Publish something you’ve written on Medium.

Don’t think you’re good enough? Have you read some of the stuff on Medium? Yes, there’s a lot of good writing on Medium and elsewhere. But I bet you could find five pieces that aren’t nearly as good as the piece you’re afraid of releasing in the world. Without even breaking a sweat.

Get in touch with your “sheer awesomeness” and “be bold and brave.” Put your work out into the world. Listen to Sara Benincasa:

“Life is too short to waste time pretending to be small and inconsequential when you are actually as vast and powerful as a distant star.”


Write better when you write more often. Join my 5-day writing challenge: Write for 15 minutes a day and I’ll donate your registration fee to a global literacy nonprofit. More info and registration link here.


Also published on Medium.

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