Anna Levesque
My guest today, Kalob Grady, calls the infamous waters of the Ottawa River home, and the 2025–2026 academic year marks his ninth year working at World Class Academy. Building off his roles as head coach and program director during his first five years, this is now Kalob’s fourth year as head of school.

Growing up on the Ottawa River, Kalob was introduced to kayaking at a young age, and the sport has influenced most of his life decisions. Throughout his career as a professional kayaker, he has represented Canada in multiple freestyle world championships and has raced against the best in the world across five continents. In addition to his competition résumé, Kalob has coached with multiple programs—from the Ottawa Kayak School in Canada, to Kayak the Nile in Uganda, Patagonia Study Abroad in Chile, and most recently, freestyle programs for local youth on the Ottawa River.

Welcome, Kalob. I’m excited you’re here—thanks for joining me.

Kalob Grady
Thank you, Anna. I really appreciate the opportunity to come on and join you on your podcast.

Anna Levesque
The first question I always start with is: when I say “discomfort zone,” what comes up for you? What does that mean to you?

Kalob Grady
When I think of the discomfort zone, I think of anything just outside your normal comfort zone to anything that really pushes your boundaries—in sport or in life. On the river, it could be a new line or a new rapid. It could be trying a new trick, putting yourself in a position to fail in front of your friends or peers.

In life, it could be those big steps or decisions—where to go to school, what career to pursue, where to live—all of which can make you uncomfortable. So, a really broad range of situations come to mind when I think about being uncomfortable.

Anna Levesque
Yeah, it is broad, and it’s in all areas of life. I love how you mentioned fear of failure in the context of trying a new trick. In kayaking, I coach my clients that it’s okay to fail—failure is part of growth. If you want to learn something new, you have to try it. There’s no way that when you’re learning something for the first time—whether it’s a freestyle trick or ferrying across more powerful current—it’s going to be perfect right away.

So, why is that idea of failure something you think about? Is it something you grapple with? And if you do, what’s your strategy? How do you approach it for yourself? And since you coach teenagers, what’s your strategy for them?

Kalob Grady
I’ll answer in reverse. In coaching teenagers, one thing they lack is a fully developed prefrontal cortex, which affects decision-making. Because the fear of physical consequence isn’t always there, the fear of social consequence often becomes more prevalent.

We work a lot on breaking down fixed mindset versus growth mindset, and we celebrate failure in low-consequence settings. This builds skills safely, helps them get uncomfortable, and shows them that failure is okay. Once they’ve built those skills, they can put them into action in scenarios where consequences are higher and failure isn’t an option.

On a personal level, I’ve definitely gone through that stage—being a teenage kayaker, trying to accomplish different things around the world. More recently, I’ve noticed that I’m most comfortable when I feel in control of the outcome. That could be a line I choose to run, or one a student is running. But as soon as I feel out of control, I get really uncomfortable.

Maybe it’s part of getting older and pushing the envelope less. Now, I’m often more fearful and uncomfortable watching other people try new things than I am doing them myself.

Anna Levesque
When you’re coaching, it’s actually good practice to focus on others—you kind of forget about yourself. That’s why you need solid skills in whatever venue you’re in, so you can set safety, watch, and cheer them on. I know that feeling of nervous excitement watching someone try something new.

Kalob Grady
Exactly. In some scenarios—safe settings—you want students to fail, and you’re totally relaxed. But then you get to bigger rapids, and while you might feel calm running them yourself or watching your peers, the moment a student steps up, your heart rate spikes. It’s a physical response to not knowing what they’ll do when they face their fear or a challenge.

Anna Levesque
There’s also the perceived lack of control that comes with kayaking. In mountain biking, rock climbing, or skiing, the surface beneath you isn’t moving—but on the river, it is. For people who crave control, that’s challenging. But it’s also one of the best reasons to try whitewater kayaking—it teaches you to work with the water. You can’t control the river, but you can control your response and how you set yourself up.

Kalob Grady
I agree. Water can seem soft, welcoming, and safe—until you add current. Then it becomes a relentless, humbling power. Once you’re locked in, you’re along for the ride, and it’s all about the skills you’ve built and how you respond in the moment.

Anna Levesque
Right. Earlier you mentioned fixed mindset versus growth mindset. What do those mean to you?

Kalob Grady
Historically, a fixed mindset is when you stick to what you’re already good at. For example, I’ve been known for doing the right air screw—it became a running joke among my friends because I loved it and did it all the time.

A growth mindset is the opposite: putting yourself in situations where you might fail, knowing that’s where the best lessons happen—ideally in low-consequence environments. If you’re in a supportive group, you’re more likely to try new things. In contrast, high-pressure environments where failure is judged can make people stick to their strengths.

Freestyle is a great way to develop that growth mindset. You can fail a hundred times on a front loop and be totally fine—and when you finally get it, the celebration fuels you to try more.

Growing up on the Ottawa River, I was lucky to have a supportive community with great coaches like Steven Wright and Mo Keller. From a young age, they encouraged me to try new things, fail, and keep going. Spending afternoons paddling with friends on different waves—bailing a bunch and still calling it a great day—shaped my approach to paddling as I moved into river running and creeking.

Anna Levesque
Yes! The Ottawa is one of my favorite rivers—beautiful, fun, and such a positive community.

Kalob Grady
Exactly. It attracts great paddlers throughout the season—both for big waves in spring and for wrapping up summer in August. As a kid, it was amazing to see top kayakers out there having fun, not just chasing the biggest waves. It shows that the best kayakers are often the ones having the most fun wherever they’re paddling.

Anna Levesque
Totally. I’ve seen that intergenerational mix on the river—it’s inspiring.

Kalob Grady
Yes. And it’s why I hope freestyle becomes “fun and cool” again, especially for younger paddlers. I think the competition scene has shrunk from its heyday in the 2000s, and while competitions give athletes goals, we need more of that middle ground—fun, low-pressure freestyle with friends. Without it, young paddlers sometimes jump straight into big river running and waterfalls, burning out after a few years.

Anna Levesque
Hmm, yeah, that’s really sad actually.

Kalob Grady
To bring it full circle, my hope and goal would be to go back to the days where everyone had a freestyle boat, and a creek boat was secondary. I know a lot of the original exploration in Chile was done with freestyle boats because people brought them to paddle the Futa. They were running the Palguin and the Fui in freestyle boats.

Anna Levesque
Yeah, which were freestyle boats back then.

Kalob Grady
Now, no one brings freestyle boats to Chile. We have half-slice boats now, which open up a whole range of hybrid ways to approach the river. But overall, I’ve seen a shift in kayaking culture away from that playful approach. I think the Southeast might have the best culture I know of in terms of “Don’t care what the level is, don’t care what boat you have—just grab something, come down to the river, and let’s go have fun.” Let’s do splats, cartwheels, squirts—whatever. Kayaking is supposed to be fun, something to do with friends. I wish more rivers and communities held onto that.

Anna Levesque
Yeah, having that love and paddling with family and friends, and the joy of connecting with the river—it’s not just something to conquer or use to show off accomplishments. It’s a living being that you can connect with and learn from.

Kalob Grady
Exactly. Not seeing the river as something to conquer, but as something to enjoy—that’s key. And bringing it back to pushing the comfort zone, I think kayaking sometimes naturally comes with that conquering mindset, but it doesn’t have to.

Anna Levesque
Right. So, what have you learned about yourself from putting yourself in the discomfort zone—not just on the river, but in your career at World Class, as head of school, and now learning to fly airplanes?

Kalob Grady
Being exposed to navigating fear and discomfort on the river from a young age has really helped me—both as a kayaker and in other areas of life. In kayaking, trusting yourself and the skills you’ve worked so hard to develop goes a long way when you’re staring at a big rapid, a waterfall, or surfing Gladiator on the Ottawa with a massive river-wide hole downstream.

When you’re uncomfortable, your heart races, your chest tightens, everything feels tense. But if you can remind yourself, “I’ve put myself in a position to succeed,” and approach it with confidence and focus, things usually go well. If, on the other hand, it feels like a roll of the dice, and you’re tense or hesitant, you don’t paddle the way you’ve trained yourself to paddle. Forward strokes get shorter, your edge control gets sloppy, and you’re more likely to make mistakes.

I’ve learned that if it feels like rolling the dice, it’s better to take a step back. Confidence keeps you relaxed and paddling well. That kind of confidence comes from a lot of exposure in lower-consequence environments, where you can push your comfort zone without big risks.

Anna Levesque
Yeah. And where do you feel confidence in your body?

Kalob Grady
Fear is easy to locate—it’s tangible. Confidence is more subtle. For me, a good example is racing at the North Fork Championships. Some years, I’d be relaxed, chatting with friends, giving fist bumps, and enjoying the moment before my run. Those were the years I raced best. Other years, I’d isolate myself, overanalyze, and get too focused on the outcome. That tension never leads to my best performance.

When I’m confident, I’m light, happy to be there, and ready to go without obsessing about the consequences. If I catch myself questioning, “How is this going to go?” I know it’s time to reset—chat with a friend, play a song—anything to relax and reconnect.

Anna Levesque
I hear that—relaxation and connection. But in kayaking, there’s always some “rolling the dice” because we can’t control the water completely.

Kalob Grady
True, but my appetite for risk has changed over the years. I want to kayak for life. My goal is to paddle the Futa at 82 years old—partly because it rhymes.

That long-term vision helps me decide in the moment: Will this rapid or waterfall deepen my love for the sport, or am I doing it because of external pressure? That perspective has kept my ego in check and allowed me to paddle big water with supportive friends where it’s okay to say, “Not today.”

Anna Levesque
I love that. And I get it—healing from my disc herniation right now, I’m so glad I listened to my inner voice on the Upper Palguin earlier this year. Knowing when to walk away is part of paddling for life.

Kalob Grady
That’s a really good story—thanks for sharing it. Your example of looking at a waterfall you’ve run countless times is something I see a lot. Many paddlers, now with careers and maybe kids, go through the phase of “I’ve always run Gorilla, so I’m going to keep running it.” Then one day they get there and decide they don’t want to run it—and they see that as the end of their kayaking.

The truth is, you can run the Green without running Gorilla.

Anna Levesque
Right. Well, now you kind of can’t—well, you can, but it’s a bit different. Anyway, I get what you’re saying.

Kalob Grady
Maybe that’s a bad example, but my point is: be okay with reshaping what kayaking looks like for you as you move into your 30s, 40s, and 50s. I’m sure you’ve seen it—people you paddled with in your 20s, then your 30s and 40s—slowly become less dependable as kayak buddies. For folks who’ve long defined themselves as “Class V kayakers,” the day they stop running that level, they start phasing out of the sport. And I’m like, I just want to kayak with you.

Anna Levesque
Yeah, for sure—and have fun. I’m grateful I’m married to someone like Andrew who still paddles Class V but can also have a blast on Class II. He paddles with his dad, who’s in his late seventies, on the Nantahala—it’s just part of a deep passion.

So, Kalob, do you have a question for me?

Kalob Grady
I’m curious—was there a moment in your career that made you start thinking about fear and discomfort differently? Or was it always something you paid attention to?

Anna Levesque
When I first started, I didn’t know much—I was just into the adventure. It was fun. I started on the Rouge River. Later, in the late ’90s when I began paddling Class V, I often felt alone. I was a good playboater from time on the Ottawa, New, and Gauley, and I’d guided rafts. When I got sponsored in 1999 for freestyle, I started touring with incredible creek boaters.

I had some creeking experience, but not much—I felt like I’d missed the Class IV progression. I was often the only woman and definitely the most nervous. That’s why I started Girls at Play: to get more women into the sport. Early on I framed it through gender; over time I realized it’s about anyone—anyone can show up nervous and still do this.

Back then, the culture wasn’t as supportive as it is now. You’d get judged for what you did or didn’t run, and I felt like there was something wrong with me. I wanted to be good. I wanted to be cool. There were supportive folks—Andrew, Dustin Knapp—but I wanted to be the person I’d needed. That’s what drew me to this work and why I want this podcast to normalize that even high-level people feel fear and approach risk with calculation.

Kalob Grady
Exactly. One of the biggest misunderstandings in today’s adventure-sports media is the assumption that athletes are thrill-seeking for external validation. In reality, most of us are calculated athletes who have trained extensively.

Anna Levesque
Right—and there’s a deep passion driving it.

Kalob Grady
Before rapid fire, one more thought on handling fear and discomfort, and why it matters whether you’re a kayaker, another type of adventure athlete, or just someone who appreciates your perspective. Alex Honnold talks about society’s lack of exposure to discomfort or fear in today’s protected world. Without that exposure, small life events—a delayed flight, a detour when you don’t have another podcast to listen to—cause outsized stress.

His point is that intentionally putting yourself in the discomfort zone builds capacity to navigate it. That’s true for me not only in kayaking but also in flying planes and working with World Class Academy around the world. When things go wrong, your body doesn’t shut down—you problem-solve. It’s the same in whitewater.

If your body’s natural response is to freeze, you lose control over the outcome. In flight training, much of the PPL/CPL work is learning what to do when the plane stops wanting to be a plane. With World Class, it’s a dynamic program: we might have students and faculty spread across multiple countries. Knowing you’ve been exposed to stress and can operate through it is huge. As Honnold puts it, if you’re always protected, the first time you’re outside your comfort zone your body can’t handle it—and then you lose control of the outcome. As we said earlier, I like having as much control as I can, on the river or anywhere else.

Anna Levesque
Yes. And for me, the discomfort zone has built self-awareness. You notice your coping mechanisms—anger, freezing, shutting down—and learn to regulate them. You realize you do have control over how you respond. That’s powerful.

Okay—rapid fire. These are meant to be answered in a sentence or less. What’s a morning ritual that sets you up for success?

Kalob Grady
Cup of water, kettle on, coffee made, play Wordle, then the first hour of emails—I feel productive right away.

Anna Levesque
What’s a non-negotiable self-care practice?

Kalob Grady
This might not sound like self-care, but I don’t need a lot of sleep most nights—then about every 10 days I need a lot. Being okay with a full 12-hour sleep shutdown day when my body asks for it is important for me.

Anna Levesque
A favorite motivational quote, book, talk, or song?

Kalob Grady
A quote I wrote in my senior year of high school—rooted in ideas I’d heard elsewhere: “I will never be the person who sells my happiness now on the bet that I can buy it back later.”

Anna Levesque
What do people get wrong about you?

Kalob Grady
Because I work for a U.S. high school and spend a lot of time with Dane, a lot of people think I’m American. I’m Canadian.

Anna Levesque
Throughout your life, have you felt like the underdog or the favorite?

Kalob Grady
Always the underdog—always a little short. It’s a healthy place to be; you learn a lot by surrounding yourself with people who are better than you.

Anna Levesque
Hard moves in easy water, or flooding?

Kalob Grady
For learning: hard moves in easy water. For adrenaline and that sense of accomplishment: high water. Nothing’s more fun than a flooded Class III that becomes massive, low-gradient big-water fun.

Anna Levesque
One word that describes your comfort zone?

Kalob Grady
My front porch.

Anna Levesque
“Freedom through discipline,” or “I do what I want”?

Kalob Grady
I usually follow “I do what I want right now,” within the bounds of long-term goals that still matter.

Anna Levesque
In one word, what do you hope your legacy will be?

Kalob Grady
Tough to do in one word, but: I’d rather be remembered for being kind than for being a kayaker.

Anna Levesque
Anything else you want to share?

Kalob Grady
I think we covered most of it. I’m an open book—if anyone has more questions, send me a message on Instagram: @kalobgrady88. If you’re ever on the Ottawa River, I kayak most days and I’m always keen to show people the magic of the Ottawa—or go for a surf. Fingers crossed the levels drop into prime freestyle soon. The kayaking community is inclusive and supportive; I’m happy to pay it forward. Don’t be a stranger—shoot me a message. And Anna, I’m grateful for the chance to talk with you today. I really enjoyed it. Thank you.

Anna Levesque
Thank you, Kalob! That’s generous—y’all should take him up on that if you’re up on the Ottawa. Thanks again for being here; I appreciate you.

Kalob Grady
Thanks, Anna. Have a great rest of your afternoon, and best of luck with your recovery. Hopefully we’ll see you back up here on the Ottawa—and also on your home river—really soon.

Anna Levesque
Thanks. Yeah, I know—that’s the worst. Honestly, the worst thing about this disc herniation is having to cancel my trip to the Ottawa. Boo. But next year.