I have been planning a road trip from Alberta to southern Ontario at the end of August.

“Planning,” however, may be too generous a word. I have been looking at maps, comparing routes, calculating driving times, checking border crossings, considering hotels, examining highways, and repeatedly asking variations of the question: What if we went this way instead?

This is what I apparently do when faced with uncertainty. I open Google Maps.

The purpose of the trip is straightforward enough. My youngest is moving into residence at art school. His sibling is coming with us, so the three of us will spend several days in a car together, crossing a substantial portion of the continent before eventually arriving at a dorm room where boxes will be carried upstairs, things will be arranged, goodbyes will be said, and I will drive away with one fewer child in the car.

But first…

There were originally three possible routes. The first was the thoroughly Canadian option: stay north of the Great Lakes and remain in Canada the entire way. There is something appealing about this. No border crossing. No currency conversion. No explaining ourselves to an American customs officer who wonders why three Canadians have apparently decided to transport an art student across the Upper Midwest.

The problem is that this route adds roughly four hours of driving. Four hours does not sound catastrophic until you add it to an already very long drive. Then four hours begins to feel less like patriotism and more like poor judgment.

The second possibility took us farther south, through Minneapolis, Indianapolis, and southern Michigan. I liked this option partly because it would allow us to visit a friend in Indianapolis, and I made my case.

My children listened. Then they noticed Chicago.

They were not enthusiastic about driving through Chicago, which is an important distinction, and not Chicago itself. Chicago may contain magnificent architecture, museums, restaurants, music, and several million perfectly decent human beings. I, for one, am a die-hard fan of Chicago blues. None of this persuaded my children that navigating its freeways in the middle of a cross-country move sounded relaxing.

I attempted advocacy, but I could also see the beginnings of resentment. One of the privileges of getting older is slowly learning that winning an argument is not always the same thing as getting a good outcome.

So, Chicago lost.

That left Route Three: northern Minnesota, Wisconsin, and Michigan. Almost immediately, it felt right.

It is not quite the shortest route. It is not the route that allows me to visit everyone I would like to see. It does, however, appear to offer the best combination of manageable driving, interesting country, and something both of my children explicitly said they wanted from the trip: they want to see the Great Lakes.

That surprised me a little. They weren’t simply asking, “How quickly can we get there?” They wanted the journey to contain something.

So we will head through the north woods, cross Wisconsin, enter Michigan’s Upper Peninsula, and make our way along some of the largest bodies of fresh water on earth. Somewhere along the way, my youngest will also get to visit a friend in Michigan.

It is, in other words, not the most efficient route. It may be the best route.

There is probably a lesson in that, although I am suspicious of turning family road trips into metaphors too quickly. Sometimes Highway 2 is just Highway 2.

Still, this particular journey is making it difficult not to notice what is happening. I am taking my youngest child to art school.

There are few things more hopeful than sending someone you love toward a life you cannot predict. Art school makes the uncertainty especially obvious. There is no sensible parental spreadsheet that can tell me exactly what he will make, who he will meet, what he will discover he is good at, what will disappoint him, what opportunities will emerge, or what kind of person will eventually come home for Christmas.

And perhaps that is true of every child leaving home. Eventually parenting requires us to accompany someone toward a future we cannot arrange for them.

You can help pack the car. You can pay attention to the route. You can remind everyone to bring their passport. You can reserve the hotel. You can even spend an unreasonable amount of time deciding whether to go above or below Lake Michigan.

But you cannot map what comes next.

There is something freeing about admitting that. A long road trip contains the same humbling truth in miniature. We have a route. We have hotels. We have border plans. We have estimated arrival times. And almost certainly, something will go wrong.

There will be construction somewhere I did not anticipate. Someone will urgently need a bathroom twenty kilometres after insisting they absolutely did not need one. We will discover a restaurant we should have stopped at only after passing it. A hotel will be stranger than its photographs. Someone will become irritated. Someone will fall asleep and miss the scenery they specifically said they wanted to see.

Perhaps we will take a wrong turn, and perhaps the wrong turn will be beautiful.

I used to think good planning meant eliminating uncertainty. Increasingly, I think good planning may mean creating enough structure that uncertainty does not frighten us when it arrives. We know where we are going. We do not know exactly how the journey will unfold.

That seems about right.

There will be several thousand kilometres of road before we reach southern Ontario. There will be Alberta, Saskatchewan, Manitoba, Grandma… and then Minnesota and Wisconsin and Michigan – and my brother’s place in Kitchener. There will be shorelines and gas stations and border crossings and probably more coffee than anyone should drink. And eventually there will be an art-school dorm room.

We will unload the car. Then, at some point, only two of us will get back into it.

I know the route home will feel different.

For now, though, the three of us are going east together, and we are taking the road with the lakes.