I challenged myself to do one new thing a month. Here’s what happened.

Updated: Aug 29, 2019

Take (At least) one small risk every single day.

In 2016, I attended a conference for creatives called the 99U conference. There were lots of very cool presentations from executives like Tristan Walker, founder of Walker & Co, a company that specializes in shaving products for black men; Jason Fried from Basecamp, the digital project collaboration platform; and Brennan Dunn, founder of Double Your Freelancing which offers online professional development for freelancers.

Three of them immediately resonated with me:

  1. Effie Brown, Executive Producer of Project Greenlight/ Duly Noted - Know Thyself: What & Why - DBAD (Don’t Be A Dick).

2. Cap Watkins, VP of design at Buzzfeed - The Buzzfeed Scale of F&!cks Given.

Genius! My closet scientist is laughing maniacally in celebration of the ability to quantify caring.

3. Yuko Shimizu, Illustrator - Take at least one small risk every single day.​

Hmmmm…interesting. How can I make this work?

Yuko told the story of how, as a struggling illustrator, she would challenge herself to do small, new things to maintain her creativity when she wasn’t working on a project. It was a way for her to stay curious, to keep experimenting and to sharpen her skills. As a result, she developed a unique aesthetic that makes her an in-demand illustrator. 

While the first two didn’t really take a lot of adaptation to be incorporated, Yuko’s message sunk in to my subconscious and bubbled its way to the surface last summer when I found myself with a bit of burnout and mental claustrophobia after a demanding project. I needed to find a way to spur my creativity. 

I decided that I would challenge myself to do one new thing a month over that summer.

And I did. 

From June to August I learned to play golf while playing in a tournament (I actually won a trophy-true story!), did a shark dive (eep!), started practicing capoeira again, and presented collages I made to a room full of artists for a critique (surprisingly, double eeep!). I found that at the end of the summer I was feeling more creative, more confident and less risk averse.

Me and my friend Keith not looking nervous at all. No sir, not at all.

This summer I’m doing the challenge with the help of my friends. So far, we’ve done moonlight kayak and mixed and bottled customized wine blends. We have more cool adventures planned that I am really looking forward to.

Making the geek chic after mixing my red wine blend. #iwillneverbecool

It’s important to stay curious and continuously find ways to challenge oneself. Even little changes to your routine can shift your perspective in meaningful ways. 

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I'm a strategic marketing communication consultant who works with premium brands to tell compelling brand stories, guide perception, drive engagement and build loyalty to win hearts and wallets. Find out more about me at, follow me on Twitter @royanndean and Linkedin.

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