For a week every month, I take a two-and-a-half-hour flight from Chicago to Winnipeg, Canada.
That might sound surprising: It’s a lot of time to spend in the air, and Chicago has so much to offer. However, I’ve been in a long-distance relationship with my Canadian partner, Andrew, for over two years, and neither of us is ready to move just yet.
Andrew and I met at a conference for financial bloggers a decade ago, and we were great friends and colleagues for many years before we became a couple.
Today, we run an online business together, which allows us to work remotely and travel regularly between our countries. Because we both have children from previous marriages, neither of us plans to move countries anytime soon.
There are challenges, but I feel like I get the best of both worlds
As an American, I’ve gotten used to certain apps, tools, and conveniences that I can’t access in Canada.
For example, Canada doesn’t have Venmo or Cash App, so Andrew and I split costs or pay each other back using Wise. If we start a movie on Hulu, we can only watch it when we’re in the States, since the streaming service isn’t available in Canada.
As inconvenient as that can be, I often feel like I get the best of both worlds. Take food, for instance: Andrew looks forward to getting Chick-fil-A when he visits me, because there isn’t a location in Winnipeg. (Although the chain does exist in some bigger Canadian cities, like Toronto.)
And, though we have A&W here in the US, it doesn’t have poutine on the menu, which is the unofficial Canadian national dish. So, I always make sure to order that when I visit him.
I’ve found that the pace and culture feel very different in both places, too. As someone who’s been self-employed for almost 15 years, I appreciate being able to surround myself with other motivated entrepreneurs whenever I’m here.
In Winnipeg and other Canadian cities I’ve visited, though, I’ve been able to slow down more. The pace feels more relaxed, and I often think of Canada as my safe haven.
In the future, we might choose both
There are also structural differences between the two places. Canadians fund their universal healthcare system through taxes, whereas a majority of Americans have private insurance.
What’s nice about Canada’s system is that residents don’t have to stress about an unexpected bill or an expensive ER visit.
That said, there can be trade-offs, like longer wait times for emergency care and surgeries. In the US, I appreciate that I can usually make medical appointments quickly, even though they come at a cost.
There are parts of American culture that will always feel hard to leave, but spending so much time in Canada has also shown me that stepping away from hustle culture can be soothing for my soul.
There are parts of American life that Andrew appreciates, too — but I know that if we live elsewhere, he’ll miss many aspects of his home, like his close-knit family and the beautiful, wide-open prairies in Winnipeg.
I’m not sure what the future holds once all our kids go to college, but we will likely spend half the year in Canada and then work remotely in a warmer area during the winter.
Whatever we choose, I know what will matter most is making sure we create a lifestyle that feels unique to us, a perfect blend of our cultures together.
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