A recent report by Robert Half found that one in three Canadian employers who cut jobs during early AI adoption have since reinstated those positions or very similar ones.
The reason? AI needed more human oversight than expected. Corporate employment isn’t just under threat from AI — it’s unpredictable in both directions.
This reinforces the core findings of VistaPrint’s recent report: when your professional stability is subject to that kind of volatility, pursuing entrepreneurship starts to look less like a risk and more like a safer bet.
For Canadian workers, the message is becoming impossible to ignore: even the most “stable” corporate jobs are increasingly at the mercy of decisions made well above their pay grade.
But as more Canadians question whether the corporate path is worth it, the data points somewhere unexpected. VistaPrint’s latest report found that 80% of small business owners say they’re happier running their own business than when they were employees. Nearly half (46%) say they’re “much happier.”
Dave DeSandre, SVP of North America, VistaPrint, discusses with Retail Insider the findings of the VistaPrint report.
Question: The data shows 80% of small business owners are happier running their own businesses than they were as employees. Is that really a mindset shift, or just a mood?
Answer: It tells us this is a mindset shift, not just a mood, and that distinction matters. A mood is reactive. What we’re seeing in the data is structural. 80 per cent of the small business owners we surveyed say they’re happier running their own business than when they were employees. Nearly half, 46 per cent, say they’re much happier. That’s a before-and-after comparison from people who have actually worked on both sides of the equation. They’re not just feeling good at the moment. They’re making a judgment call, and the verdict is clear.
What’s driving that? 54 per cent cite flexibility in their schedule as a key contributor to their happiness, and 41 per cent point to doing work they’re genuinely passionate about. The majority of Canadian entrepreneurs are telling us their satisfaction comes from how and why they work, not just what they earn. That’s a fundamental reframe of what success looks like, and it’s showing up in their confidence too. 77 per cent say they’re confident in their ability to grow over the next 12 months. These aren’t people in a defensive crouch. They’re planning for what’s next.
Q: There’s a lot of anxiety right now about AI displacing workers. Where does entrepreneurship fit into that story?
A: The AI narrative has been told almost entirely from the employee’s perspective: who’s at risk, what companies are restructuring. That’s a real story and it matters. But there’s a parallel story that isn’t getting nearly enough attention: the same technology is genuinely leveling the playing field for entrepreneurs.
Design, marketing, analytics, content creation. Capabilities that used to require entire teams or significant budgets are now accessible to a solo operator. The barrier between a one-person shop and a mid-size company has never been lower. Our data reflects this. 80 per cent of Canadian small business owners are already using AI at least monthly, and 72 per cent say it’s had a positive impact on their happiness.
That’s not a coincidence. It’s freeing up time and mental bandwidth that entrepreneurs are redirecting toward the work that actually matters to them. The AI economy has disrupted a lot, but for entrepreneurs who lean into these tools, it’s created an opening.
Q: The list of major Canadian employers making cuts keeps growing, with AI cited as a driving force.What does that wave of corporate disruption actually have to do with entrepreneurship?
A: For some it forces people to ask a question they’d been putting off. Who actually controls my future? For a long time, the implicit answer was stay at a big company and build seniority. That calculus is changing in the minds of some.
What our data captures is the other side of that reckoning. Canadians aren’t just leaving corporate environments out of frustration. They’re arriving at entrepreneurship with a clear-eyed view of what they’re getting in return: autonomy, flexibility, and the ability to make meaningful decisions about their own work.
This isn’t the honeymoon effect that fades once the reality of a business sets in. Two-thirds (67 per cent) of small business owners tell us they’re happier now than when they first opened their doors. The further people get from traditional employment, the more the decision validates itself.
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