Relocation

In August 2021, I relocated from Chicago to Toronto with my entire family. It was a major move—personally, professionally, and culturally. And like any big transition, it came with moments of uncertainty, unexpected hurdles, and also, immense growth.

This wasn’t my first experience working abroad—I had previously spent two years living and working in Venice, Italy. But at that time, I was younger, single, and traveling light. Relocating to a new country with a partner, children, and a growing career is a completely different challenge—and opportunity. Three years on from arriving and just one year back in the US, I’m going to reflect on what that meant for me and the opportunities I discovered.

The Challenges: Uncertainty, Adaptation, and Starting from Scratch

We moved mid-COVID, when travel restrictions and safety concerns made it impossible to visit Toronto beforehand. That meant we had to find housing remotely—no in-person viewings, no weekend scouting trips, just Zoom walkthroughs and a leap of faith. It was stressful, to say the least, even with the support of the company.

Then came the cultural transition. While the U.S. and Canada share much on the surface, I quickly learned that business culture can be very different. From communication styles to regulatory frameworks, I had to adapt my leadership approach and relearn how to navigate stakeholder relationships in a new context. Even simple things like setting expectations, decision-making pace, or navigating humor in meetings took recalibration.

And socially? We started from zero. No local network, no weekend meetups, no pre-existing community to lean on. Building new friendships and support systems takes time—and intentionality. It’s something no job description or relocation package fully prepares you for.

The Positives: Professional Growth and Perspective

The upside was significant. I stepped into a more senior leadership role—one that challenged me to stretch my strategic planning capabilities and gain real-time exposure to an entirely new market. Managing logistics in Canada during an ongoing global supply chain crisis forced me to deepen my understanding of regional nuance.

Canada is not the U.S. when it comes to logistics. The market structure is leaner, with a much smaller set of national carrier options. Purolator and Canada Post are the only two full-coverage parcel providers, which means supply chain leaders have less flexibility and greater exposure to risk if disruptions hit. I experienced this firsthand during the Vancouver port strikes, the British Columbia floods, and other disruptions that exposed the fragility of key transportation arteries across the country.

This concentration also has major implications for reverse logistics. Canada's geography—vast and sparsely populated in many regions—makes returns particularly challenging. With limited carrier coverage and long last-mile routes, facilitating consumer returns is significantly more costly and time-consuming than in the U.S. In rural areas especially, the reverse flow of goods can be so inefficient that it affects customer satisfaction and operational sustainability. It taught me to think more creatively about product life cycles, circularity, and how to bake resilience into both forward and reverse flows.

These challenges sharpened my leadership muscles. I had to adapt network strategies, stretch my planning approach, and think more creatively than ever before. It was one of the most accelerated learning periods in my career.

Another fascinating discovery was the uniqueness of Canada’s retail landscape. Major players here aren’t necessarily household names elsewhere. Canadian Tire, for example, is one of the largest and most influential retailers in the country—yet virtually unknown outside its borders. Meanwhile, Hudson’s Bay, a legacy retailer with deep roots, is actually older than the United States itself. These companies operate in a different competitive environment, often with a greater focus on multi-purpose physical stores and hybrid fulfillment models. Understanding these distinctions wasn’t just educational—it helped me develop more regionally informed, customer-centric strategies and appreciate how deeply logistics is shaped by culture, history, and infrastructure.

Relocation as a Stepping Stone for Broader Leadership

One of the most overlooked benefits of relocation is how it can serve as a strategic stepping stone for career advancement. Moving into a smaller market—like Canada compared to the U.S.—often means inheriting a broader scope of responsibility. In my case, I stepped into a role that required me to oversee multiple functions, expand my influence cross-functionally, and take ownership of regional strategy.

From an Individual Development Plan (IDP) perspective, this type of move hits the “70% Experience” sweet spot—a real-world challenge that accelerates growth by forcing you to apply new skills in unfamiliar territory. For anyone looking to build executive readiness, a relocation assignment can be one of the most powerful, practical ways to gain that next-level experience.

Reflections for Leaders Considering Relocation

Relocating for work isn’t easy—but it can be transformational. It forces you to develop flexibility, cultural intelligence, and resilience. It demands that you listen more, assume less, and grow faster. It makes you a more empathetic leader, because you’ve experienced the discomfort of being the outsider, of rebuilding from the ground up.

But it also comes with a responsibility. If you're leading teams across borders or welcoming colleagues who are relocating, understand the full picture. Make space for adaptation. Be proactive in supporting integration—not just into the job, but into the community and culture as well.

For anyone contemplating a move like this: do it with eyes open. Yes, it’s hard. But it’s also one of the most rewarding professional and personal decisions you can make. You won’t just change your geography—you’ll change your perspective, your leadership, and your legacy.

A photo of Toronto I took during my commute, 2022

So many boxes…