Art and Fear

I’ve been carrying around a book I might never read.

The book is currently sitting on my bedside table. Since I left my job at TrainingPeaks to pursue freelance writing two weeks ago, it’s gone with me everywhere.

On top of my underwear, extra socks, ski goggles and water bottle, this book gets stuffed into my backpack for multi-day trips into the mountains. It goes into my purse when I head to the coffee shop for the day. I know I don’t have time to read it on these outings, but I bring it anyway, because it is a reminder I want to keep close by.

It’s a small, light paperback simply titled, Art and Fear, and a friend gave it to me in early January to encourage me to write more. Inside the cover, he had scrawled a simple note that made me stop breathing for just a moment, because he had no idea I was contemplating a transition at the time, and because I was searching so desperately for a sign:

“To my talented friend Gloria. Chase your dreams, don’t just think about it.”


The words Art and Fear mean a lot to me because of another book I once read about the creative process. In The War of Art, Steven Pressfield says that if you’re not sure what you’re passionate about or what your “art” is, simply ask yourself what you’re most afraid of:

Fear is good. Like self-doubt, fear is an indicator. Fear tells us what we have to do…The more scared we are of a work or calling, the more sure we can be that we have to do it.

I read these words in 2009 when I was sitting on the 31 bus on the way down to my big girl job in the financial district of San Francisco, some dreary weekday morning. I remember putting the book down for a minute and looking out the window, thinking about all the things I that scared me most. Once I moved past the phobias like heights and big, leggy jungle spiders, one thing stood out. Writing.

If you know me, you know I am great at losing stuff. So I lost this knowledge too. I stowed this revelation away somewhere safe and then promptly forgot where I put it for another few years. Even after moving to Colorado and deciding to make my first career change, I thought maybe I wanted to do PR or marketing, which incorporated elements of writing but are by no means “writing jobs”.

I was still in denial about what I really wanted. I had to try something else first, because trying to be a writer was so terrifying it didn’t even seem like a realistic prospect.

And so it took me 2.5 more years, which I am grateful for, but more on that later. In the end, the decision came to me on an airplane headed to Mexico, in the creativity forced out by cramped Economy seating, in the clarity that can only be found at the cruising altitude of a jetliner. On the back of a Google Maps printout, I scrawled the responses to a question I had never been able to answer in my life: “Who do you want to be in 5 years? How about 10?” When I was done, I felt like I had excavated a long-lost piece of my heart onto that sheet of paper.

If you want to know who that person is, here is the best way I can describe her: I met the editorial director for a major outdoor publication last month. He’s written an award-winning book about Everest, been the editor on the print and digital sides of this publication for over 15 years, and writes beautifully with a touch of humor. He’s also traveled all over the US and the world accomplishing some impressive athletic feats. As a human being, he is super smart and incredibly accomplished…yet so genuine and down to earth that it humbled me.

If I can be him in 15 years, I will be very happy with how I have spent my career and my time.


Chasing your dream is really scary. Leaving the safe harbor of TrainingPeaks, I was full of fears:

I am afraid I got lucky in my last career change, but that I won’t be as lucky this time around. I am afraid that all those “signs from the universe” were just coincidences, or worse, the universe is actually aligning to teach me a very expensive and poignant lesson. I’m afraid I’ll let down the people who have gone out on a limb to give me my first opportunities. I’m afraid I’ll pick up too much free work to get paid work, or too much paid work that doesn’t fulfill my goals, and that either way I’ll run out of my money and then realize I didn’t accomplish what I set out to do. I’m afraid that I don’t have the pedigree or the talent to become the caliber of writer I’d like to be. Even more than rejection, I am afraid of being so unimportant, I am simply ignored. I’m also afraid to be really poor.

So, there’s Fear. But there’s also one more thing: Work.


I learned a lot about work in the past few years. The bike taught me about work: how to show up every day and sweat, good days and bad. My coworkers at TrainingPeaks taught me about work: they were swimming laps in the pool at 5 am when most people were still curled up in their beds. The athletes we wrote about taught me about work: that work equates with resilience, and that the most successful individuals are not the ones who are most talented but the ones who bounce back fastest after setbacks. They also taught me that you can be good if you are hardworking, or good if you are talented, but when talent and hard work intersect—then, you can be great.

Maybe the best way I’ve heard someone put it is this—a response from advice columnist “Sugar” (bestselling author Cheryl Strayed) to a young woman suffering from writer’s block:

You’re up too high and down too low. Neither is the place where we get any work done. We get the work done on the ground level. And the kindest thing I can do for you is to tell you to get your ass on the floor. I know it’s hard to write, darling. But it’s harder not to. The only way you’ll find out if you ‘have it in you’ is to get to work and see if you do. The only way to override your ‘limitations, insecurities, jealousies, and ineptitude’ is to produce…So write. Not like a girl. Not like a boy. Write like a motherfucker.


The thing with both Art and Fear is that you can’t hang around dwelling on either of them for too long.

Art is ephemeral, especially for me, right now. What I’m creating today is not yet “art” (there is a fantastic video that talks about the gap between our taste and our skill when we are just starting). And having grandiose notions about the art I might create, one day, gets me nowhere: “You’re up too high.”

Fear is paralyzing. Thinking too hard about all the scary things that could happen doesn’t further my goal, and it only takes up valuable mental bandwidth that could be devoted to writing. “You’re down too low.”

When we work though, we are “on the ground level”. Work is movement, which progresses us forward. Work is practice, which makes us more proficient. Work is hard, which makes us better people. Work is productive, which gives us something tangible.

Yes, we should find our Art. And when we do we’ll find Fear, its silent companion. But when we have accepted that the two come hand in hand, and that it’s normal to be scared, then it’s time to move forward and make things happen. It’s time to get to Work. Because work is the antidote to fear.

I think I may finally leave that book at home today.

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