I’ve had a lot of conversations with leaders over the years. Most of them are about growth, succession, team dynamics, pressure, uncertainty — the familiar terrain of running something that matters.
My conversation with Mark Gasparotto was different.
Mark spent just over twenty years in the Canadian Army as a combat engineer officer. He led soldiers through Bosnia, Kabul, Kandahar, and Haiti. He was part of Operation Medusa — Canada’s largest combat operation since Korea. He’s been blown up. He’s buried a soldier. He’s sent people home wounded.
Today he runs The Gasparotto Group, helping business leaders build the mindset and resilience to lead through pressure. And when I asked him what keeps him up at night now that he’s an entrepreneur, he didn’t miss a beat.
“Making payroll. And some days, I wish for the simplicity of a gunfight, quite frankly.”
I’ve been in enough boardrooms to know that line lands differently depending on who’s in the room. For anyone who’s carried real responsibility — the kind where the consequences are yours and nobody else’s — it makes complete sense.
Humility Before Authority
Mark didn’t come into the military thinking he was built for it. He told me that his infantry training in Chilliwack was the first moment he realized natural ability would only take him so far.
“It broke me down to some core elements. Some of the weaker parts of my character came out — and I didn’t like what I saw.”
That kind of honesty is rare. Most leaders I work with have a version of that story — the moment they realized they weren’t as prepared as they thought — but few of them say it out loud, and fewer still learned from it as cleanly as Mark did.
His first posting after training put him in command of thirty to forty soldiers, paired with a twenty-year veteran who knew far more about the job than he did. The Army does that deliberately, he told me. Cognitive and experiential diversity. You’re technically in charge, but you’d better be humble about what you don’t know.
That’s a lesson that translates directly into business. I’ve seen leaders struggle for years because they couldn’t hold both things at once — authority and humility. Mark had to learn it early, in conditions where getting it wrong had real consequences.
What It Means to Struggle Well
The phrase Mark kept coming back to was struggle well.
Not survive struggle. Not get through it. Struggle well — meaning with intention, with preparation, with some understanding of what’s actually happening to you when things get hard.
He breaks resilience into two frameworks, and both of them stuck with me.
The first is a table with four legs: body, mind, heart, and soul. The tabletop is your relationships. That’s your whole humanity — physical, intellectual, emotional, spiritual, relational. If one of those legs is weak or missing, you’re still standing. Until you put enough pressure in the right place.
The second is about time. Resilience before adversity — what are you doing to prepare? Resilience during — how do you perform when it’s live? And resilience after — how do you actually recover, not just get back to functional?
Most leaders I work with have thought seriously about the middle part. The before and after get less attention. That’s usually where the gaps are.
The Line That Stayed With Me
The line that stayed with me longest from our conversation wasn’t about combat. It was this:
“Most people don’t rise to the occasion in crisis. They fall to the level of their training — or the level of their systems.”
I’ve seen that play out in business more times than I can count. The leader who held it together wasn’t the one who performed best under pressure in the moment. It was the one who had done the work beforehand — the thinking, the preparation, the honest assessment of where they were weak.
That’s not an insight unique to the military. But it’s stated more clearly by someone who’s actually tested it in conditions where the margin for error is zero.
