Blog #7 - The Traveling Entrepreneur Part #2 : Building the Canadian Dream

The Traveling Entrepreneur – Part #2: Building the Canadian Dream

In my last blog, I explored the American Dream and how it reveals itself differently depending on the city. Chicago made me want to build. San Francisco made me think twice.

But what about here at home? Does Canada even have a version of the American Dream? Is all hope lost for entrepreneurs in Canada? Or are we still trying to figure out what that dream could and should be?

After exploring the complex, vibrant, and sometimes contradictory landscapes of the American Dream, my journey continues closer to home. As an aspiring Canadian entrepreneur, I find myself asking: what does success look like here? What is the Canadian Dream—and how can it be built, nurtured, and shared?

Canada’s entrepreneurial spirit may not roar as loudly or glamorously as its southern neighbor’s, but it carries its own unique strengths. Here, success is often rooted in community, resilience, and a deep respect for personal growth. Yet, I’ve also noticed that the Canadian Dream can feel quieter, more modest, and sometimes harder to define.

In this blog, I explore four iconic Canadian cities—Ottawa, Toronto, Quebec City, and Charlottetown—to see if there’s something emerging that we could call “The Canadian Dream.”


Ottawa: Ambition in a Government Town

I was born in Ottawa, raised just outside in Kemptville, Ontario, and spent part of my post-secondary years here before moving east for business school. So, I’ve seen the city through two lenses: before and after my entrepreneurial mindset awakening.

Ottawa is growing steadily. It’s decently clean, proud, and full of people with big goals. Yet it’s also the Canadian government town—and that reality shapes its culture, economy, and opportunities in profound ways. I often see Ottawa as a city where entrepreneurship comes to die.

Many people I’ve met both in my personal and professional lives have brilliant ideas, strong skills, and undeniable talent. But often, those ideas remain just that—ideas. The stability of a government job looms large. It’s seen as “safe,” “comfortable,” even “prestigious.” With benefits like early retirement, solid pensions, and job security, the incentive to take entrepreneurial risks becomes low. The promise of steady paychecks often outweighs the uncertainty and hustle that building a business demands.

I’ve witnessed firsthand how this comfort can breed complacency. In many departments, inefficiency is tolerated and even expected—ten people doing what one person might manage in the private sector, processes bogged down in layers of bureaucracy, innovation slowed by risk aversion and a lack of responsibility that leads to wasteful spending.

But underneath this culture of caution, there’s unmistakable ambition. Ottawa’s entrepreneurial spirit is quiet but persistent. The city has incubators, tech hubs, and co-working spaces trying to nurture start-ups and innovation but at its core, lacks in true business support a city needs to become iconic. There are sparks of energy among younger generations who don’t want to settle for traditional paths.

Still, the challenge remains: how to break through the cultural inertia? How to shift the mindset from “secure” to “bold,” from “comfortable” to “creative” and I think potentially most important from “small idea” to “Big business”

Ottawa feels like a city on the cusp, full of untapped potential waiting for a catalyst—someone or something to ignite that spark and inspire risk-taking, collaboration, and a new vision of success beyond government work. The dream here exists, but in my opinion needs to be ignited as Ottawa in a few words is sadly “Somewhat boring" with the potential to be iconic.


Toronto: Canada’s not quite, New York City

Last summer, I returned to Toronto and revisited some iconic spots—the CN Tower, the Royal Ontario Museum, Kensington Market, and the F1 Exhibition. Growing up, I remembered Toronto as a city pulsing with life and vibrancy, a place where culture, creativity, and ambition seemed to collide on every corner. But now? It feels different—more fragmented, more transactional and absolutely no personality.

Downtown Toronto is a sea of hurried people, all moving in different directions yet strangely disconnected. Faces are often glued to screens; strangers brush past without a glance. The city seems desperate to mimic New York’s relentless energy and stature, but it’s missing the intangible cultural backbone—the lived-in grit, the organic communities, and the messy, layered stories that give a place soul. Toronto feels polished but somewhat hollow, a shiny shell without the beating heart inside.

Yet, what surprised me most was the charm I found—not in the glittering downtown, but on the edges.

Near the airport, I visited Woodbine Mall, a place clearly showing its age. It’s a fading relic of a past retail boom—empty storefronts, dated signage, and quiet hallways. But beneath that surface of decline, there was something else: resilience. Neighbors still meet and talk in its corridors, families come for affordable shopping, and local vendors hold on. The sense of community, though quiet, persists.

With a casino being constructed across the street and a wave of new condos rising nearby, this struggling mall might just hold the key to becoming the epicenter of a future neighborhood revival. It represents a space where real people live and work, a patch of opportunity overlooked by the city’s glitzy ambitions.

Toronto’s story seems split between the dazzling but impersonal downtown core and the overlooked, human-scale suburbs and side streets. While the city wrestles with rapid growth, housing crises, cost of living, and cultural shifts, these peripheral communities offer a different kind of promise—a chance to build something grounded in authentic connection and tangible need.

For entrepreneurs, this duality is both challenge and opportunity. The downtown rush may feel saturated and competitive, but the outskirts hold untapped potential for community-focused innovation. Building the Canadian Dream in Toronto may not mean replicating New York’s hustle—it may mean rediscovering local roots and investing where the real people are then building a culture and identity from there.


Quebec City: Culture Over Commerce

Quebec City surprised me. I came looking for the French-Canadian version of the Canadian Dream—and instead found the cultural capital of the province, a place where history and identity are not just preserved but fiercely celebrated as the foundation of everything the city is and could become.

Every street corner tells a story. Walking through Old Quebec is like stepping into a living tapestry of heritage: centuries-old stone buildings, cobblestone streets, statues honoring key figures, and vibrant public art that reflect a proud, enduring French-Canadian identity. Unlike many modern cities that often try to erase or gloss over their pasts in favor of “progress,” Quebec City wears its history openly, embedding it into daily life.

From a purely economic or entrepreneurial standpoint, Quebec City doesn’t claim the frenetic pace or high-tech ambition of Toronto or Vancouver. It’s quieter, less dominated by start-up culture or rapid scaling ventures. Entrepreneurship here takes a different shape—one that is more cautious, community-oriented, and often deeply intertwined with cultural preservation and local identity. Small one-off shops are more prevalent than large companies. The local shops may not hold the millions that entrepreneurs often seek however they are wealthy in personality and culture.

This leads to a crucial insight: the Canadian Dream, as Quebec City shows us, might not be about chasing fast growth or competing on a global economic stage. Instead, it could begin with pride—a grounded, collective pride in language, heritage, and community. Here, success is measured not just by financial gain but by how business and culture can coexist and reinforce one another.

Quebec City challenges the prevailing notion of entrepreneurship by showing that economic development can and should be aligned with cultural continuity. The city’s small businesses, artisanal shops, local food producers, and cultural festivals all thrive because they honor tradition while adapting to today’s realities. This approach creates a sustainable ecosystem where commerce supports culture rather than displacing it.

Linking back to earlier reflections on cities like Toronto and Ottawa—where the dream can feel fractured between ambition and comfort, hustle and disconnection—Quebec City offers a different model. It asks: What if the Canadian Dream isn’t just about building bigger or faster, but about building deeper? About valuing roots as much as growth, identity as much as innovation?

This perspective is vital for Canada as a whole, a country advertised as being built on diverse cultures, histories, and languages, but with no real national identity. The Canadian Dream may ultimately need to be plural—a mosaic of dreams reflecting the distinct realities of places like Ottawa, Toronto, Quebec City, and beyond. Quebec City reminds us that entrepreneurship here can be a force for cultural affirmation as much as economic advancement.


Charlottetown: The Dream on a Small Scale

Charlottetown is personal for me. I lived on Prince Edward Island for six years, attended business school there, and spent many summers visiting my grand parents, specifically as it relates to this blog my entrepreneurial grandfather—who, through his example, made me believe this small city was quietly humming with potential.

In many ways, Charlottetown is a business hub, but it’s a different kind of hub. It’s small, intimate, and embraces a slower pace. Here, entrepreneurship exists but tends to be modest in scope. The risks entrepreneurs take are measured, and the rewards, while meaningful, are more contained than in larger urban centers. The mentality leans toward stability, community, and sustainability rather than rapid growth or high-stakes disruption.

This more cautious approach may at first seem limiting, but it reveals a fundamental aspect of the Canadian Dream that’s often overlooked. Maybe the dream here isn’t about chasing the next big thing or scaling up quickly—it’s about doing work that feels fulfilling, building something sustainable, and maintaining a balance between ambition and security.

For many in Charlottetown, I believe the Canadian dream is safe, respectable, and quiet. It’s about taking chances, but not risking everything. It’s about nurturing a local business that supports family and community. It’s about contributing to a shared way of life where success is defined not just by financial gain but by quality of life and connection to place.

When I reflect on Charlottetown alongside cities like Ottawa, Toronto and Quebec City, it becomes clear that the Canadian Dream isn’t a single story but a mosaic of many—ranging from bold ambition to steady perseverance, from cultural pride to cautious entrepreneurship. Charlottetown embodies the smaller-scale, heart-centered dream that balances hope with humility.


The truth is, Canada doesn’t have a clear, defined version of “The Canadian Dream” — partly because we struggle with a cohesive national identity that doesn’t really exist outside of “We’re not American”

Where the American Dream celebrates bold ambition, risk-taking, and the relentless pursuit of success, the Canadian mindset often leans toward modesty, caution, and security. We take pride in our healthcare system, our reputation for politeness, and our social safety nets. But when it comes to business innovation or global ambition, we often hold ourselves back to take the safe route.

Right now, if the Canadian Dream exists at all, it tends to be a quiet one: get a decent education, land a stable government or corporate job, buy a house (if you can), and enjoy a safe, peaceful, quiet life. There’s absolutely nothing wrong with that. In fact, it’s a model of stability many admire. But for a new generation of dreamers, builders, and creators, it may feel uninspiring—too small, too safe, too cautious.

So, what could the Canadian Dream become?

It could be a bold fusion of our strongest values — safety, community, being welcoming etc — with a renewed willingness to take risks. Having a dream where we build global companies from small town ambitions, where culture and creativity are not afterthoughts but central drivers of our economy, and where entrepreneurship is celebrated as much as public service.

To realize this, we have to stop being ashamed or apologetic about our culture, our history, or our uniquely Canadian ways of doing things. We need to start taking a page from the American book by thinking bigger, building bolder, and embracing risk—not recklessly, but with confidence and conviction.

The Canadian Dream could become a vision for building something with deep purpose, not just profit. But to get there, we need a shift in mindset and to grow a backbone. We need to believe that we are capable of more—and to support those who dare to push entrepreneurial boundaries.

It’s not about 100% copying the American Dream or mimicking any other model. It’s about defining a new dream—one rooted in who we are and who we want to become.

And maybe, just maybe, this is the generation that finally makes that dream real.

 


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