Leadership Is An Infinite Game

screenshot 2025 09 12 at 3.31.33 pm

Last night I had the privilege of standing shoulder-to-shoulder with Atlantic Business Magazine Top 50 CEOs.

As I looked around the room, I saw creators—the people who stare straight at problems that would paralyze most and say, “Let’s build.”

Nassim Taleb once argued that entrepreneurs deserve the same respect we afford soldiers; statistically, our odds of “success” aren’t great, yet we still charge the hill. Why?

Because leadership is an infinite game—there is no finish line, only the daily obligation to earn the right to play tomorrow.

Some reflections from the evening:

1. Relentless uncertainty, deliberate creation.

From COVID to mass inflation to Economic warfare, the hits don’t stop. But that’s precisely when builders choose to lead.

2. The power of aligned urgency.

Chrystia Freeland graciously thanked the business community and promptly challenged our community to champion the elimination of inter-provincial barriers. support the energy corridors, and drive productivity (And god do we need to do this). With the economic and sovereign threats pointed out way, this is Canada’s time.We either lean in now or miss a generational opportunity.

3. Growth in public, discomfort in private.

The first time I was recognized, I felt wildly out of place. Four ceremonies later, I understand the point: pause, take stock, and take a moment to celebrate what our teams are building while.

Gratitude Roll-Call

First off, to our team Symplicity Designs – It was an honour to share last night with you. Thank you Sarah Gallant, Mary Beth Tingley, MA, CPHR, Evelyn Bannister, and Zachary Knopp thank you for joining me last night. Without your leadership, we don’t succeed. Chris Johnston & Mark Symes were busy leading our next cohort of Levership

I could tag dozens, but I want to make sure to say a special congrats to Margaret Melanson – We’ve been in the trenches together and I know your leadership first hand. Well deserved. Laura Kanaan and Mathew Benvie congrats on your first one! I love what we’re building. Bradley Farquhar and Courtney Sherlock thank you for being part of my tribe at EO Atlantic Canada

John Flewelling, P.Eng. – Humble, curious, razor-sharp. Your leadership of CBCL Limited, with over 500 employees, is what we need as we build Canada. My team said “He has good vibes.” Your table agreed, they erupted after hearing your name three times—including Atlantic Canada’s 2025 Top CEO – Congrats! Well Deserved!

To every leader honored—and to the teams that make the impossible look routine—thank you for proving that Atlantic Canada doesn’t wait for opportunity; we manufacture it.

Here’s to earning the right to plan tomorrow—together.

And yes – The hat was a tribute to Dad.

I miss him dearly. This is the first year he wasn’t with me at the ceremony. Without him, none of this is possible. I know that I stand on the shoulders of a giant. We all do Symplicity Designs.

WANT TO READ MORE?

Follow Matt on LinkedIn to stay up-to-date on his posts in real time and subscribe to his newsletter