Travel Light #2: entrepreneurial thinking is the missing link to creativity

"The intellect is always looking for a map, but the intuition only needs a compass. --Martha Beck

If creativity helps us discover what longs to be expressed, entrepreneurial thinking helps it find its place in the world.

Creativity is our inner curiosity, listening to intuition, desire, and inspiration. Entrepreneurial thinking is our outer curiosity, exploring people, systems, and opportunities. Creativity asks, "What feels alive here?" Entrepreneurial thinking asks, "How might this find its place in the world?

Entrepreneurial thinking isn't necessarily about starting a business

Entrepreneurial thinking isn't synonymous with starting a business; a business is only one possible vehicle. The deeper question is: what form allows this creative impulse to reach the people it is meant to reach?

When I first started a theatre festival that eventually became Canada's largest ten-minute play festival, I had no intention of turning it into a business. In fact, had that been my primary goal, I doubt I could have built it with the same creativity and integrity.

I've also seen creatives start businesses primarily to fulfill their own creative needs, which can become a trap. A business ultimately has to serve others, not just ourselves. Creativity can, and often should, find many different expressions.

Testing and the feedback loop

Creativity flourishes when we're free to play, following our inclinations to discover what wants to emerge. Entrepreneurial thinking takes that essence and experiments with it, assuming the first expression of an idea is rarely its final form.

The key is creating a feedback loop. Creativity and entrepreneurial thinking aren't separate stages so much as overlapping conversations. Imagine you've spent nine months writing poetry on your own. Eventually, your entrepreneurial thinking nudges you toward a local poetry reading. You arrive feeling slightly intimidated but soon discover an encouraging community. You hear others read, share your own work, receive honest feedback, and realize you've found a place where your creativity can continue to grow.

The hidden creative

What do these people have in common?The retired farmer with drawers of unpublished poetry. The schoolteacher who wrote novels for forty years without showing anyone. The amateur photographer whose family discovered thousands of carefully catalogued negatives only after his death. The work existed. It simply never found its way into the world.

Creating for ourselves is reason enough to be creative. But entrepreneurial thinking deepens the experience by inviting connection—with others and with ourselves. Our creative work often longs for relationship. We're social creatures. Like our friendships, our art seeks intimacy.

When momentum replaces meaning

In my own life, I've come to see how important it is to stay connected to one's creative source. When I was running the theatre festival, I began because I loved stories and helping people discover their creative voices. As the festival grew, I spent more and more time writing grant applications, recruiting volunteers, managing budgets, and organizing schedules. I became a highly efficient organizer. But I stopped directing, stopped writing, stopped teaching playwriting workshops. I became disconnected from the very thing that had inspired me to begin.

Entrepreneurial thinking can create tremendous momentum. But without reconnecting to creativity, that momentum can carry us further from the work that first gave it meaning.

I had to remind myself that creativity acts as a compass, while entrepreneurial thinking provides the energy and means to move.

Without periodically checking the compass, it's possible to travel a great distance in a direction that no longer feels true. When we see creativity as inner curiosity and entrepreneurial thinking as outer curiosity working together, something quietly remarkable happens. They're the same impulse, simply directed inward and outward at once.

The unexpected thread

For years, painter Emily Carr couldn't sell her work or find an audience. Critics and much of Victoria had little interest in her paintings of British Columbia's forests and Indigenous villages. To keep painting, she ran a boarding house she nicknamed the "House of All Sorts." She raised sheepdogs, made pottery, and hooked rugs she simplified for tourists so they would actually sell. None of those things were the destination. They were scaffolding—a way to keep the real work alive until the world was ready for it. Recognition didn't come until Carr was in her fifties. By then, she'd spent decades doing the quiet, unglamorous work of creating the conditions that allowed her creativity to survive.

It's a useful corrective to the myth that entrepreneurial thinking is always about bold pitches and big swings. Sometimes it's a boarding house. Sometimes it's a rug made for someone who'll never know what else you create.

The vehicle doesn't have to be glamorous. It simply has to keep your compass pointed in the right direction.

The entrepreneurial thinking creed

1.     Entrepreneurial thinking is the curious search for where your creative impulse belongs in the world.

2.     It's not necessarily about starting a business. It's about finding the right vehicle for what your creativity reveals.

3.     Testing your creative work in the world helps you discover who it serves and how it grows.

4.     You will be tempted, at some point, or many points, to chase momentum instead of meaning.

5.     No one can guarantee the world will meet you there. But if you keep returning to your compass, you'll never lose your direction.

6.     Entrepreneurial thinking, paired with creativity, leads to work that feels both meaningful and alive.

Till next time. Travel light.