Creativity Lives in a Dark Place, In the Mystery of Not Knowing.

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I had the torn-out Yellow Pages for "bicycle shops” spread across a Montreal city map on the passenger seat of my rental vehicle. In the back of the Chevy wagon, jammed in beside my luggage, was our first Sherpa “all terrain bike.”

“There’s the next store. Why do I feel so nervous?” I muttered, turning into the slushy curbside parking spot.

I hoisted the Sherpa over a snowbank onto the soggy sidewalk. A young guy held the door open; he wore a ponytail and a denim shop apron labeled “François”.

“Merci, François. Parlez-vous anglais?”

“Yes, a little.”

“I’m Grayson Bain, from Vancouver. We have a new bike called the Rocky Mountain Sherpa. It’s an all-terrain bike.”

Francois crouched down, ran his fingers along the wide knobby tire, and asked, “Who would you sell this to?”

I had the answer ready. “It’s riders who want to go off on mountain trails.”

He stood and lifted the bike. “Oof. What are people supposed to do with something this heavy?” He pointed to a lineup of sleek French and Japanese 10-speeds. “That’s what people are buying. They’re fast. Light.”

“Yeah they’re also fragile. We’ve found that people are frustrated with how easily they break,” I replied.

François shook his head and stepped back. “You’re wrong. We don’t even have mountains close by. You’ll never sell that thing in Quebec.”

In less than fifteen minutes, I was back outside. Feet wet, heart heavy.

That cold Montreal day in early 1985, I wasn’t just discouraged—I was disoriented. My ex-partner Jacob Heilbron, who had recently left the company, would have handled this trip better. He spoke French. He was a racer. I was still trying to adjust to his absence, still trying to decide if I could carry the vision forward alone.

While most stores blamed broken 10-speeds on “user error”, Jacob and I saw it as a design failure. That belief, paired with Jacob’s optimism and my financial tenacity, birthed the first wave of Canadian mountain bikes.

Jacob was gone, and my persistence didn’t spare me from the feeling of rejection. It’s easy to say, “Look at the success you’ve had, Grayson!" But that certainly wasn’t clear to me in 1985.

Uncertainty speaks loudly. “This isn’t good enough, you’ve got to start again.”

In my last post, I wrote about quitting the paper route. I had to create a reason to get out of bed at 4am on cold, wet mornings. I have grown to love the rush of creativity, but to get there I’ve had to live in disorientation, in painful places. I’ve had to move forward without proof. To risk being misunderstood, or even unseen. Dark times are where creativity can be birthed.

I keep asking probing questions of myself about innovation. Each time I’ve created something innovative, I remain unsure whether what I’m doing is foolish or visionary. It can take years to find out. And while I’ve spent the time persisting in the project, I’ve had to learn to live with all my self-doubt.

But I’ve come to believe that doubting myself is part of the process. Sometimes it signals that something honest is trying to break through.

Montreal wasn’t just a failed sales trip. It was a test of emotional tenacity. Every “no” I heard that week was a blow to my ego. And if I’d listened to the fear and defensiveness rising in me, I might’ve walked away from the idea altogether. But I kept showing up anyway.

That’s what creative effort looks like – stepping forward even when you don’t know how it will end.

But this isn’t just about a new product, called “Sherpa”. This is about living life.

It might be the familiar, well-trodden life that's dulling your sense of joy and aliveness. Look for the untamed path, where mystery lives, where outcomes are uncertain. It’s often in this fog of doubt and the mist of discomfort that creativity awakens again.

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I would love to connect with you on LinkedIn, Facebook, or Instagram​

See you next week,

Grayson

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