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If you’ve spent any time around youth sports, you know the obsession with “AAA.” It’s the top tier, the big leagues before the big leagues. Parents whisper about it in arenas, and their kids pin their self-worth to it. Coaches act like making it is the only thing that matters. As a parent, I get it—there’s this weird social pressure to make sure your kid is on “the best team.” You find yourself scanning rosters, comparing tryout lists, and wondering if you’re ruining their future because they’re in AA instead of AAA (or God help you, house league!). As if future happiness is determined at age 9 with a pair of skates.

Personally, I don’t think double or triple letters are always the best place for a kid. Some thrive. Others burn out. Some are just playing the wrong sport altogether. You can grind your way up to competitive-level hockey and still be miserable if, deep down, you were meant for soccer, or track, or playing guitar in the basement.

That’s the trap: with the right skills and a little bit of luck, you can make it to the highest level of the wrong game. From the outside, it looks like success; from the inside, it might be quite the struggle.

This trap has defined a good chunk of my career, a decade in product management. On paper, it looked like the dream: influence, visibility, high-stakes decisions. I was in the room where things happened. And I was good at it—just like some kids are good enough to make AAA even if it’s not their natural game. I built roadmaps, ran prioritization sessions, wrangled stakeholders, and lived in the land of trade-offs.

But… it always felt… off. Like I was running a marathon in a weighted vest. Meetings drained me. Wins felt like relief, not joy. Often, I didn’t want to wake up in the morning. It took many years for me to realize that deep down, I knew I was out of position. This wasn’t obvious right away—I convinced myself for years that my struggles were just part of the gig.

Building Something From Nothing

After a layoff, I caught a break and stumbled back into my game. Almost immediately, I felt how different it was to be in the right place. That realization hit hard when I rejoined Telus a few years ago. The company wanted to enter the smart home space—they had a business case, but no product. No roadmap. No definition beyond “we should do this.”

I led design on what would become their new SmartHome+ app. In less than a year, a scrappy team of us designed it from the ground up. And here’s the thing: design wasn’t just decorating the edges—we were instrumental in defining the product. We set the vision, mapped the journeys, decided what mattered first, and collaborated with engineering to make it real. It was messy and intense, but the work with my design team felt right.

Now, a year and a half after I moved on, Telus is still shipping features based on our design foundation. Stuff we sketched and argued about back then is just now hitting production. I don’t know what the team is doing day-to-day anymore, but it’s strangely validating to see those ideas still alive and being built. It’s like leaving behind blueprints and coming back to see the house not only built but with new wings still being added.

There was a big gap in the cultural fit for me (I had left Telus years before for a reason), but that experience is when it clicked for me: this is what it feels like to be in the right game. The long hours didn’t grind me down—they energized me. Instead of dragging myself through prioritization meetings, I was excited to shape the direction.

Shaping What’s Already There

Fast forward to today: I’m at Coveo, leading a team of designers in a very different setup. No blank canvas. No greenfield product. Instead, I inherited a team working on a mature platform in one of the most competitive spaces imaginable: AI.

Coveo has always been about technical depth. Our products are built on precision, scale, and sheer engineering prowess. But now the opportunity is to win on experience. To make the power of our AI feel effortless and indispensable to the people using it. Walking into that, my first job wasn’t to “revolutionize design.” It was to stabilize:

• Get clarity on roles in a restructured team.
• Sit down one-on-one with people throughout the company to actually listen to what is working (and what is broken).
• Prioritize what matters most across people, processes, and eventually, product.

And here’s the irony: all those product management skills I carried like baggage? Suddenly, they’re jet fuel. Juggling backlog prioritization, trade-off discussions, and stakeholder alignment all felt like survival tactics during my time in product management. In design leadership, these skills and my experience over the years now amplify my strengths. I’m not forcing myself to play the wrong game anymore; I’m using skills from other games to excel in the right one.

Twenty Years, Many Teams

Looking back, my career reads like a closet full of mismatched jerseys. Agencies. Small companies. Corporate gigs. Large enterprises. Product management. Design leadership. Some of those moves definitely felt like wrong turns at the time. But here’s the truth: every stint taught me something I carry now.

It’s like spending a season in the wrong sport. Maybe you weren’t cut out to be a rower, but 5 a.m. practices still drilled discipline into you. Maybe your coach was a hardass about conditioning, and that toughness stuck. The wrong game can still prepare you for the right one.

That’s what product did for me. It toughened me up. It taught me patience and how to navigate endless ambiguity. And now, in design leadership, those lessons are assets—not weights.

Choose the Game, Not the Jersey

The AAA Trap is seductive. Prestige hits hard at first, but the crash comes fast. You keep climbing because you can, because everyone around you cheers when you make the cut. But the truth is brutal: the wrong game at the highest level is still the wrong game.

The right game doesn’t necessarily feel easier. It’s still hard work, long hours, and tough calls. But it feels different. The hard work energizes instead of draining. The wins feel like fuel, not relief. And the impact lasts—like seeing a product you helped define continue to ship features years later, or watching a team you stabilized grow into its stride.

If you’re thinking about switching sports yourself, here’s the short version of my playbook:

• Track your energy, not just your résumé. Pay attention to what gives you flow versus what feels like slog.
• Reframe detours as training (both in your mind and on your résumé). Practicing at the wrong game still builds muscles you’ll use later.
• Don’t confuse prestige with fit. The “AAA” title doesn’t mean you’re in the right sport.
• Expect to start fresh, but not empty. A pivot might reset your role, but you’re carrying transferable skills (and scars).

In the end, it’s not about making the AAA team. It’s about knowing whether you’re playing the right sport in the first place—and having the courage to switch when you finally realize what that is.