From startup dreams to self-made plans

Startups may be media darlings, but for many Canadians, they’re still more of a supporting act in their career journey rather than the headline role. That disconnect raises a bigger question: what do workers really want, and what does it mean for the future of work in Canada?

According to Employment Hero’s 2025 Annual Jobs Report, only 2% of Canadians say working at a startup is their ideal job. In contrast, 22% dream of working for themselves or owning their own business. For workers aged 55 and over, that number jumps to 32%. This isn’t a fluke, it’s a signal. Canadians are prioritizing purpose, flexibility and self-direction, particularly later in their careers.

But this isn’t a rejection of ambition. It’s a redefinition of risk. Taking a role at a startup often means betting on someone else’s big idea — and that can be exciting, fast-paced, and rewarding, but it also comes with unpredictability. Self-employment carries its own risks, but they’re different: you set the pace, and you own the outcomes. Both paths have their benefits, but the choice between them is something weighing on many Canadians’ minds today.

Dana Buxcey knows that trade-off well. After building her career as Director of Growth at tbk, helping scale one of Ontario’s top digital agencies, she launched twoseven — a full-service marketing agency focused on brand strategy, social media and design. She kept a full-time job while building her business, a decision rooted in both practicality and long-term vision.

“For me, it wasn’t about escaping the 9-to-5,” Dana says. “It was about building financial security and autonomy. I wanted to grow something of my own, but not at the expense of stability.”

Dana’s story reflects a deeper cultural shift. The idea that entrepreneurship equals freedom has always been more myth than reality and many Canadians are waking up to that. “People assume being your own boss means freedom from structure,” she says. “But when you’re running a business, it’s often 5 a.m. to 9 p.m. The hustle is real, especially in the early years.”

And while platforms and social media may give the illusion of overnight success, Dana is quick to dispel that too. “Having 20,000 followers doesn’t mean you’re making money,” she says. “It just means you have an audience. There’s a lot of survival-mode hustle that gets glossed over.”

So why are more Canadians taking the plunge into self-employment, and why later in life?

According to Dana, it comes down to confidence and clarity. “By your 30s, 40s or 50s, you’ve built networks, savings, maybe a home. You’ve got more to fall back on and you’re probably tired of doing work that doesn’t align with your values.”

In other words, it’s not burnout. It’s intentionality. “People are ready to do what drives them,” Dana says. “They’re not chasing hype. They’re following experience.”

That doesn’t mean entrepreneurship is easy — especially in a high-cost environment. Dana recommends starting small and staying strategic: “Keep your full-time job if you can. Start your business on the side, model your costs, and have at least $10,000 to $15,000 saved. And lean on your network — talk to people who understand tax, insurance, and the benefits you’ll lose once you leave traditional employment.”

But this shift isn’t about chasing a dream. It’s about designing a reality that feels more sustainable, more meaningful and more in tune with what matters. Canadians aren’t turning away from work — they’re turning toward themselves.

That’s not something employers can counter with perks or job titles. It’s a signal that the default career path is changing — and for many, self-employment is becoming the most viable version of success. For startups, that means leaning into what makes you different: offering growth, clarity and overcommunication so people feel like they’re building with you, not betting on you.

The future of work in Canada won’t be led by who’s hiring — it’ll be shaped by who’s building.