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Keep Doing Awkward Things

Last week Jon Acuff hosted a meetup in OKC and I had the opportunity to go. He talked about his upcoming book, Do Over, authenticity, of course fear, and also bravery. He's told us before in his work that bravery doesn’t feel like we’re bareback on a horse, face half-painted blue, spear in hand. Sometimes it feels more like walking by the bully in 7th grade, knowing there’s a 99% chance we’ll end up stuffed in a locker.

I thought about what bravery had felt like for me lately: Awkward.

Sending tweets directly to Tony Robbins, telling him I sent his team an “exciting opportunity!” to help promote my book. Opportunity? What exactly do I have to offer Tony Robbins? Oh yea, that’s right, NOTHING. His secretary emailed me one of the many polite rejections I received. That’s awkward. 

Emailing Arianna Huffington like we were acquaintances, asking her for an endorsement because I was “joining her in the ranks of female business authors”. As if we are literary equals. That’s awkward.

Showing up at Launch Out months ago, asking the first person I recognized from Facebook if I could sit next to her. It was about as awkward as it sounds.

Sending Jon a video message from my kitchen table (after multiple emails) explaining to him all the reasons my message matters to some of his tribe. It was next-level awkward.

After sharing some of the above at the meet up,

Jon encouraged us to “Keep doing awkward things.” You know who else probably felt really uncomfortable when in reality, they were being brave:

Let’s see - Rosa Parks? Bet that whole deal on the bus was awkward. Steve Jobs? Hey, guys, I know I left the company a few years ago but I’m baaa-aaaaack! #awkward. Remember how awkward it was when little Taylor Swift sang Tim McGraw to Tim McGraw back in 2006?! - I almost turned my TV off. Abraham Lincoln hired everyone who opposed him to serve on his cabinet after he was elected. The awkwardmeter must’ve broken at their first meeting. Actors have made entire careers from being awkward (I’m looking at you Zooey Deschanel.) I’m sure you can think of awkward leaders in your own life, right? Or awkward changes that ended up being the best thing ever?

Even though awkward is funny, and maybe even popular right now, (again, you, Zooey) don’t be fooled. It’s not fun. I wasn’t really eating or sleeping much the week I was sending those emails and making those videos. I had a lot of teary, red-faced, I-hope-even-mom-didn’t-see-that-grovel-tweet moments. So I’m NOT encouraging you to start sending pathetic emails or make strange videos in your kitchen. UNLESS that’s what you need to do for your dream. Unless your hustle requires it. In that case, saddle up. Get your spear, my friends. Embrace all that nausea and sweat and hand-wringing because eventually, it pays off. Keep on walking just like you did in middle school. There’s still a chance you’ll end up in a locker, but eventually you’ll reach the other side and with a sigh of relief, you’ll realize, hey, that was pretty brave.


What has bravery looked like for you lately? How do you overcome your fears?

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