From "someday" to "today"

Driving across the country with our kids isn't something my wife and I decided to do on a whim. We've talked about it for years. Even before our kids were born, we would imagine a camper van and the open road and children who behave impeccably when stuck in a vehicle together multiple hours.

But even as our early-relationship selves described the trips we would one day take, we knew we were speaking in hypotheticals. It was a far-off dream, safely filed under someday.

As our family grew, we came back to the idea periodically, but there was always a reason that now wasn't the time. But someday it would be time.

Someday we'd pack up the kids and do a real adventure. Not a week at a cottage or a long weekend in New York — a real one. The kind where you're gone long enough that you forget what day it is, where the car becomes a second home and you realize that years from now, this adventure will be a milestone in your life; all other events will be remembered as "pre-trip" and "post-trip".

Someday.

The thing about someday is that it's a very comfortable place to live. It costs nothing, risks nothing, and it never disappoints you. The trip in your head is always perfect. The weather is great, the kids are enthusiastic, and nobody argues about what to listen to for the first four hours out of Toronto.

I've been thinking a lot lately about something the therapist and author Lori Gottlieb writes about — the idea that when most of us say we want our life stories to change, what we actually want is for someone else in our story to change. We're waiting for the right conditions, the right moment, the right version of ourselves to show up and make it happen. We want a different character to move the plot forward. But that's not how it works. You're not a character in your own life. You're the protagonist. Protagonists are the ones who need to change in order for the story arc to take shape.

I have a poster on my classroom wall that I often point to when my students are in the early stages of the writing process. It says: "Ideas are useless until you get them out of your head and see what they can do." It's true, and it makes a nice poster, but like most catchy one-line inspirational quotes, it's easy to say, hard to do.

Four years ago, my wife and I got the idea out of our heads and started planning how we could save money, take time off work, and out of our heads and on to the road.

In other words: we stopped saying someday and started saying summer of 2026.

In 2022, saying 2026 still felt a long way off. We had only just taken our first major post-COVID trip - a fantastic tour of Newfoundland that only strengthened our resolve to show our kids the rest of the country - so planning something so ambitious felt a bit risky.

But we're doing it. Two weeks from today, our family is starting the eastern leg of our cross-country road trip, from Toronto to PEI and back. In September we'll complete the western journey, driving from Toronto to Vancouver to Whitehorse and back.

We're going to visit playgrounds from coast to coast — which, after years of reviewing Toronto's playgrounds on Danforth Dad, feels like the most natural possible evolution of this little project.

We're going to stand at the Terry Fox memorial near Thunder Bay right around the anniversary of the day he was forced to stop running. We're going to drive through the Prairies and the Rockies and the BC interior, and fly up to the Yukon, and show our kids that Canada is so much bigger and wilder and more beautiful than the neighbourhood we love so much.

Our kids are 9 and 11. They're approaching the end of what I've always thought of as their peak playgrounding years — the age where a great playground can still make a whole afternoon disappear. This trip feels like a way to honour that, to stretch it out a little, before they grow into the kind of kids who are too cool for slides.

Along the way, we're raising funds for Canadian Tire Jumpstart, an organization that works to make sure kids across Canada have access to sport, play, and physical activity regardless of their family's financial situation. Because if this trip is about anything, it's about the belief that play matters — for kids, for families, for communities. If you feel the same way, we'd love your support.

But mostly, I'm writing this first post to say: whatever your someday is, I hope this trip nudges you a little. Not because our adventure is special — but because yours is too, and it's waiting for you to stop filing it away.

The country is waiting. Let's go play.