Why the bravest thing you can do is start before you feel ready.
Confidence is not a prerequisite for starting; it is a byproduct of doing.
We often wait for a surge of certainty before we launch a project, sign a lease, or pitch a collaboration. But in the world of grassroots arts leadership, certainty is a luxury we rarely afford. The most transformative projects in history didn’t begin with a polished five-year plan; they began with a “let’s see what happens” attitude and a high tolerance for the awkward.
If you are feeling discouraged because things aren’t moving as fast as you hoped, or because your last event didn’t go as planned, remember that you are currently in the most vital stage of growth: the messy middle.
Why is this mindset so critical for young leaders? Because the pressure to appear “established” can stifle the very creativity that makes your organization unique. When we are afraid to make mistakes, we default to the safest, most boring versions of our ideas. We copy what the big galleries are doing because it feels proven. But the world doesn’t need another miniature version of a corporate museum. It needs your specific, unpolished, and daring vision.
Discouragement is often just the gap between our taste and our current skill level. Bridging that gap takes time, and more importantly, it takes a lot of “failed” experiments.
To navigate this, we must adopt the “Crazy Idea” protocol. This means intentionally carving out space for projects that have a high probability of failure but a high reward for learning. If you are running a community zine, maybe you try a one-night-only “invisible” gallery. If you are a theater collective, maybe you perform in a moving bus.
These aren’t just stunts; they are stress tests for your creativity. When you try something wild and it doesn’t work, you haven’t lost anything—you’ve gained information. You’ve learned about your audience, your logistics, and your own resilience. This is how you build true confidence. It’s not the belief that you will always succeed, but the knowledge that you can handle it when you don’t.
Furthermore, we have to respect the timeline of community building. Trust isn’t something you can optimize with a software update. It is built through the slow, consistent act of showing up, even when the room is half-empty. All things of lasting value take time to take root. Think of your organization as a garden, not a factory.
There will be seasons of planting where nothing seems to be happening on the surface, but the roots are stretching deep into the soil. Discouragement is often just a lack of perspective on what season you are currently in.
Finally, give yourself permission to be a beginner. The future optimist knows that the current landscape is meant to be reshaped, and that reshaping is a noisy, iterative process. Your mistakes are not signs that you are a failure; they are signs that you are actually in the game. The only way to avoid mistakes is to do nothing, and doing nothing is the only true risk.
Keep your eyes on the horizon, but keep your hands in the dirt.
The future you are building is made of these small, brave, imperfect moments.
Be bold enough to try the things that scare you, and be patient enough to let them grow. You are doing better than you think you are.
Northern Arts and Regional Innovation
This is a collaborative initiative by The Arts Incubator Winnipeg and the Art Borups Corners art collective, supporting artists and creative projects in Melgund Township, Northwestern Ontario. Our groups champion rural arts development, community programming, Indigenous arts partnerships, and cultural innovation—strengthening the local and regional arts sector through mentorship, exhibitions, digital media, and sustainable creative entrepreneurship. Our events and activities include artists from Melgund Township, Winnipeg, Ignace, Sioux Lookout, Dryden, and beyond. You read more innovation-focused posts here.
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