Congratulations to Brad Pickard for Winning the January 2023 Barefoot Writing Challenge! (Your $100 prize is on its way!)

The challenge was to write an essay that answered this prompt:

Choose one guiding word to steer you toward your paid writing goals for the coming year, and explain why you chose it

Brad channeled legendary ice hockey player Wayne Gretzky to talk about the most effective way to boost confidence. Enjoy his winning submission:



by Brad Pickard

Brad Pickard
Brad Pickard

The great ice hockey player Wayne Gretzky is credited with saying, “The day I stop learning is the day I stop growing. You miss 100% of the shots you don’t take.”

So why have I been so afraid to take risks in my life?

After all, according to Wayne, the only way to grow is to learn. And the only way to learn, sadly, is to fail. Repeatedly.

For me, the fear of failure is extremely scary — almost as scary as the fear of… success.

Becoming fearless has become a recent obsession — one that I’m consciously choosing to guide my writing journey this year.

If I’m not willing to risk failure or success, though, where does that leave me?

Stuck. Overwhelmed. And immobilized by fear.

I don’t believe I lack talent. What I do lack, though, is confidence — confidence to go out on a limb with a client or to declare my fees without apologizing.

But confidence — for me, at least — only comes with experience. And the first time I try something new, by definition, I don’t have any.

So, to gain experience, I realize I need to fail, learn, and grow — in that order. There is simply no getting around successes and failures in life, unfortunately.

But wait a minute!

What’s so scary about success, anyway? Isn’t that what I should want?

I believed for years that if I succeeded at something, then in the process, I must have pushed others down. Which feels intolerable to me.

Hence my pickle…

So, if I don’t lack talent, then why have I never been paid to write? My best guess is… because…

I haven’t submitted anything. Not even once…

Until now.

You see, early in my life, I avoided all forms of risk. It felt safer. But what I later realized is the biggest risk anyone can take is… doing nothing.

Think about it for a minute. Doing nothing is a huge risk — with a known outcome.

For instance, as a clarinetist, I never played in a professional orchestra. Why?

Because I never auditioned.

In other words, I missed my shot because I never took it. Thus, the outcome was clear: a 100% chance of failure.

Then what have I done instead for all this time? Largely, I’ve done nothing… other than distract myself from my true desires in life. And focus on other people’s dreams.

Again, it felt safer. At least temporarily.

When I chose fearless as my guiding word for 2023, it was already infused with meaning from an experience I’d had several weeks prior.

Shortly before Christmas, I did something I’d never done before. Over the phone, I spontaneously pitched myself to a small-business owner. That’s right!

It wasn’t the reason for my call. And the idea only dawned on me during our conversation.

I nearly talked myself out of it. Like I usually do.

But I’m glad I gave it a shot. Because if I hadn’t, I would’ve missed a chance to both learn and grow.

Plus… I wouldn’t have scored my first client.