The extreme sport of megaprojects.

What kitesurfing has taught me about business and myself. 

I’ve been caught in sudden storms, barely making it back to shore. I’ve seen kitesurfers—some far more experienced than me—get yanked high into the air by unpredictable gusts, only to come crashing down. One tragic story that still lingers in my mind is that of Jason 'Ghostrider' Maloney, an Ontario kiter who was thought to be too skilled to be taken by the sport he loved. But when a sudden wind picked him up and slammed him back down, he fell unconscious and never made it back.

I’ve watched lightning strike near Cherry Beach, kites turning into unintended lightning rods as the sky darkened too fast for comfort. And then there’s winter kiting—an entirely different beast. The moment you hit that ice-cold water, the clock starts ticking. Hypothermia isn’t a possibility; it’s a certainty. I’ve always had a dry suit, but I’ve seen people out there in wetsuits, pushing their limits. If they go down, they’ve got about 30 minutes before things turn deadly.

So, why do I find this relaxing during my time off?

How I Fell (Literally) Into Kitesurfing 

Before I begin, please know you have my permission to fully skip this section if you actually don’t care to listen to me geek out about the kitesurfing stuff and just want to get to the business stuff. 

The first time I saw someone kitesurfing was at Mont Tremblant. I was snowboarding, making my way down the mountain, when I spotted a lone figure gliding effortlessly across the frozen lake below, pulled by a massive kite. It looked surreal—completely different from the rigid, gravity-bound experience of snowboarding. I was hooked before I even tried it.

At the time, I was already bored with the limited snowboarding options in the east, so I thought, why not snowkiting? It seemed like the natural evolution of my winter sports experience. That February or March, as the season was winding down, I started taking lessons in a field, trying to figure out how to navigate the kite. It was humbling.

My first real attempts were at Woodbine Beach in Toronto—on frozen sand, not even in the water. I had a 7-metre kite, zero experience, and a whole lot of confidence from watching YouTube videos. In theory, it made sense. In reality, I bought a skateboard designed for kiting, got pulled half a metre into the air, and came crashing down. My ankle swelled up so badly I was bedridden for four days. That was my first hard lesson: learning on land hurts a lot more than learning in water.I wasn’t deterred. I kept watching videos, convinced I could figure it out, but eventually realized I needed to start in water if I wanted to avoid more broken bones.

That’s when I went home to Lake Garda in Italy. Water training was a completely different experience. It took a week before I could even stand, but when I finally did, it was exhilarating. From there, things escalated.I bought my own equipment and tried Lake Simcoe, but without much knowledge of kites or wind conditions, I found myself doing the “walk of shame”—the frustrating trek back to shore after the wind dies or you misjudge your position. I had no idea how to choose the right kite, how to read wind shifts, or how to manage the technical aspects of the sport.

So, I went back to learning. In 2016, I took more lessons in North Carolina. By 2017 and 2018, I was struggling through kiting sessions at Cherry Beach in Toronto—where there was little room to launch, unreliable wind, and fully prepared to take the ferry back from the island in case I miscalculated the conditions. I still thought Lake Simcoe was my best bet, but even there, I ran into the same problem: if the wind disappeared, you had to swim back.

By then, I had long abandoned the idea of snowkiting. It had seemed like a great concept at the start, but after two sessions on frozen lakes with no snow cover—just raw, hard ice—it felt like a terrible idea. If you fell, you weren’t landing on powder; you were hitting ice at full speed. The sport that had originally drawn me in was no longer a factor.

By 2019, I had fully transitioned into dedicated kitesurfing trips. That year, I did a 300-km, six-day trip with a group of like-minded riders—five from Canada, four from the UK. I had just bought a new board without straps (which everyone later told me I should’ve gotten with straps), but at that point, I was committed. That same year, I took a Christmas trip back to Brazil with my wife, Divya, where I continued pushing my limits. I moved beyond just learning the twin-tip board and started experimenting with a surfboard and a foil board—each of which required relearning how to kite.

Twin-tip riding is mostly about kite control—80% kite, 20% board. You spend your first few sessions obsessively watching the kite, making sure you don’t send yourself flying into the water. But eventually, your awareness shifts. You stop looking at the kite and start feeling it through the tension in the lines and the pull on your board. It becomes second nature.

Much like the start of a career, the beginning is all about taking in as much information as possible—industry trends, best practices, technical knowledge. But eventually, you stop looking at the details and start operating by instinct.

Lessons from Kiting and Megaprojects

So, why after long stressful months in my career do I choose to unwind with a seemingly stressful extreme sport?  Watching the waves isn’t mentally exhausting—it’s the only time my mind is fully present. Even on weekends, work is always in the background, but when I’m kitesurfing, there’s no room for distraction. In a society that constantly pulls our attention in different directions, I get the rare privilege of focusing on just one thing. The moment my mind drifts back to work, I fall. Kitesurfing demands 100% of my attention—and for that I love it. But here I am, back at my desk after another kitesurfing trip and of course, thinking about work and the unique parallels of kitesurfing and megaprojects. 

1. Conditions change quickly—knowledge is your best defense.

The answer, oddly enough, is control. Kitesurfing might look like a reckless sport—flying over waves, catching wind, moving at speeds that would make any reasonable person hesitate—but the truth is, it’s all about preparation. Understanding the wind is everything. Before launching, you need to know the direction, the strength, and what it means for your session. Toronto has clean east and south winds, but offshore winds? That’s a one-way ticket to a long, miserable swim back to shore. You always have to assess whether you’re dealing with normal wind or storm-driven wind—because one carries you smoothly, while the other can drag you into a situation you can’t escape from.

Much like in megaprojects, stepping into the unknown without preparation invites failure. You don’t launch into a market without understanding the forces at play, scale without testing the waters, or assume success just because something worked before. Success—whether making it back to shore or winning a multi-million dollar bid—comes from equipping yourself with expert knowledge and the right tools.

2. Know when to let go. 

The biggest mistake in kitesurfing is holding on when you should be letting go. I’ve had my kite lines cross with another rider’s—two kites tangled, two people being dragged toward disaster. The only solution? Release on time.Pull the safety release and let it all go, even if it means losing an expensive kite. Holding on too long only makes the situation worse.

In megaprojects, this happens all the time. Teams hold onto flawed strategies, pushing forward due to sunk costs. Projects that should be re-evaluated continue because too much has already been invested. But sometimes, the smartest move is to let go and redirect resources before the damage compounds.

3. Conserve your energy.  

There’s a rule in kitesurfing: the more tired you are, the more you fall, and the more you fall, the more exhausted you become. It’s a vicious cycle. Energy management is key. If you push too hard, you’ll burn out—on the water or in your career.

I’ve learned to recognize when it’s time to come in. When the legs start shaking, when I start making mistakes, when I’m no longer in control—it’s time to stop. In business, we rarely acknowledge these moments. We push through exhaustion, glorifying hustle over sustainability. But just like in kitesurfing, knowing when to pause is just as important as knowing when to push forward.

4. Adapt or fail.

The biggest failure I ever had in kitesurfing wasn’t a dramatic crash or a near-death experience. It was something simple—my harness hook broke, leaving my kite attached only by a safety thin leash. In that moment, I had two choices: panic and hold on, or trust what I had learned and let go. I chose the latter. I let go of the bar, grabbed the centre lines, and used them to retrieve my kite. The situation was bad, but because I had trained for it, I adapted.

Megaprojects often face a similar dilemma: it’s not always the “headline” disasters that cause the most chaos, but rather a single, critical point of failure that goes overlooked until it snaps. Maybe a key supplier drops out, a subtle regulatory shift throws the timeline off, or a crucial piece of technology falters without warning. Leaders have two options: they can cling to the original plan out of fear—worsening the damage—or they can trust in their contingency training and “let go” of what no longer works. By calmly pivoting, reallocating resources, or restructuring processes, a project can be reeled back under control. Just as in kitesurfing, the real test is your ability to respond in the heat of the moment—knowing that the biggest threats aren’t always the most obvious, and that your capacity to adapt is what keeps everything from unraveling.

Success in megaprojects isn’t about avoiding failure. It’s about being prepared for it, knowing how to pivot, and trusting that adaptation is the only way forward.

Anyone want to kite with me?

Kitesurfing demands full attention. Every second, you're reading the wind, adjusting your stance, and reacting to shifting conditions. The moment your mind drifts—toward work, emails, or anything else—you fall.

That’s what makes it so powerful. It’s one of the few times my mind isn’t being pulled in a dozen directions. No distractions, no decisions beyond what’s happening in that exact moment. Pure focus. In business and leadership, the same level of presence is essential. Lose focus, and you make poor decisions. Stop paying attention, and opportunities slip by. Push too hard, and fatigue leads to costly mistakes.

Kitesurfing is an extreme sport. So is business. Both are unpredictable, demand constant adaptation, and punish hesitation. But when you master the fundamentals—reading the wind, knowing when to let go, and staying fully present—you stop fighting the chaos and start riding it. And that’s when it gets fun.