Eight years ago, and a few weeks before Calgarians headed to the polls in a civic plebiscite to decide whether to bid for these 2026 Games, I wrote a piece titled An Olympic Sized Opportunity, which I’d encourage you to read again before reading on, and concluded, rather unequivocally, that the answer was an obvious Yes. “Isn’t this a complete no-brainer?” I asked rhetorically.

Ah, the intemperance of youth. Wrong I was. Caution won. And Calgary lost.

Of course, there are people who will say we got it right in 2018—and not without reason. The modern Olympics carry a lot of legitimate baggage. Host cities have watched budgets balloon far beyond original projections, with cost overruns and taxpayers left holding the bag long after the circus leaves town. Security requirements have become massive, expensive, and increasingly sobering, and the world we live in is far more complicated than the one that once celebrated amateur sport and shared optimism, and certainly than the one that existed last time Calgary hosted, in 1988, nearly four decades ago. The Olympic brand itself has taken a beating in those intervening years, tarnished by corruption, backroom dealing, and governance failures that make it feel, at times, less like a celebration of human excellence and more a case study in institutional graft.

Still, I couldn’t shake the feeling that here was this little town in northern Italy simply going for it—improving its infrastructure, leveraging federal and regional dollars for local and lasting benefit, building new highways and transit and, best I could tell, underground water mains that appeared to be working. It made me wonder what Calgary might look like today had it leveraged the federal and provincial dollars on offer eight years ago. Had we tapped into the legacy and spirit of the ’88 Games, and demonstrated to the world—and particularly to our mercurial and imperialistic neighbour to the south, what Canada is capable of when it chooses confidence over caution.

Calgary could have advanced long-discussed legacy projects: improved regional and airport transit connections, like a train from the airport to downtown, you know, like Vancouver has; modern multi-sport facilities, renewed investment in Canada Olympic Park, housing tied to transit, and public spaces designed for long-term community use. These were not speculative ambitions, but practical projects already on the civic horizon—initiatives that would have strengthened the city’s infrastructure, competitiveness, and quality of life for decades. Calgary would have continued to grow and invest regardless—and indeed, some of these projects are now underway. It’s not as though Calgary is sitting idle on those backless metal McMahon bleachers staring wistfully at an unlit cauldron. We are building. We are investing. The new arena, Arts Commons, East Village, the broader Rivers District and entertainment district are real, ambitious, city-shaping projects. Calgary is not stagnant—far from it.

The question, however, was whether we wished to harness a unique moment to do so with greater coordination, urgency, and lasting impact and to do so using federal dollars that—for once—would have flowed into our province, rather than out of it.

Looking back, older and wiser, this, to me, is about more than just sport. It’s about decision-making. It’s about leadership. And, to bring it back to what we do around our firm every day, it’s about the one that got away; the hire we didn’t make.

Sometimes the risk isn’t making the wrong choice—it’s making a careful one without conviction. And that, I believe, is what happened with Calgary’s Olympic bid. We obsessed over the how and forgot the why. We tiptoed around neutrality and process while the opportunity itself slipped away. We faced a mobilized, on-message “No” campaign and countered it with Eddie-the-Eagle nostalgia and dutiful but uninspired economic analysis. We let “fancy process,” as I wrote in 2018, substitute for leadership.

And in the end, caution prevailed—not just in a Games bid, but as a habit. A reflex to manage risk rather than make a case, to avoid conviction rather than articulate it. In a different era, that might have been forgivable. In this one—where infrastructure, influence, and democratic confidence are increasingly contested—hesitation doesn’t remain neutral for long. When capable cities and countries decline to lead, others are eager to fill the space, unburdened by process, doubt, or democratic restraint. And history suggests that’s rarely how the good guys win.

I see the same dynamic play out in executive search. As in civic life, decisiveness and boldness are often mistaken for the same thing—and neither survives long in committee. Boards deliberate. They chase ever-elusive consensus. They want just one more option. To de-risk, to justify, to cover their hind end. That’s rarely how anything memorable gets built.

And then the candidate walks—often right across the street, to the competitor who knew what they wanted and had the conviction to act. The missed hire is almost always remembered more vividly than the ones actually made.

Cities, even countries, aren’t so different. The 1988 Olympics transformed Calgary—building infrastructure, galvanizing volunteers, attracting global attention, and leaving a legacy still visible today. The 2026 Games could have been another chapter in that story—renewing venues, inspiring a generation, reigniting civic and national pride. Instead, we chose caution over aspiration. And here we sit, talking about crumbling feeder mains. Or, as Calgary’s new Mayor put it recently, a water system “sick, dying and terminally ill” Not exactly Faster, Higher, Stronger.

And so, while Cortina—population 5,700—stepped up, a community energized by something larger than itself, Calgary watches from a distance. In hiring as in hosting, you don’t build legacies with timidity. You don’t inspire with caution. The missed hire is remembered vividly by those who hesitated—but the world moves on.

To be fair, the hire you did make often works out just fine. Let’s face it, most of us are those hires. Calgary has continued to grow and prosper without the Games. But fine isn’t transformative. And for a place that calls itself the Blue Sky City, signalling endless possibility, it’s hard not to wonder what might have been possible had we moved a little faster, reached a little higher, been a little stronger. Of course, the Olympics are messy, expensive, and complicated—just as hiring a truly transformational leader carries risk. But risk is the price of relevance. When the why is clear, the danger isn’t acting—it’s dithering.

That’s how I feel about the Olympics. Caution quietly closes doors. The great candidate doesn’t vanish—they simply go lead somewhere else. The Games didn’t disappear—they just landed in Cortina. The opportunity moved on. And that, in the end, is the lesson I keep coming back to. You don’t build legacies with excessive caution. You don’t inspire people by hedging. And no one—no board, no city, no generation—is remembered for the hire they didn’t make, literal or proverbial.

As I said at the top, regret isn’t something I spend much time with—and I don’t intend to start now. It has done its job, though: reminding me that doors rarely announce when they’re about to close. And so I’ll do what I’m far more comfortable with than regret, which is looking forward. Forward to the moments still to come—the cheers, the tears, the medals, the memories—even if they’re watched from the couch rather than the stands. 

With that, I’ll say, Go Canada! 🇨🇦

Regards,

Adam