All Aboard the Leadership Special
Platform 9¾ Isn’t the Only Magic on Trains. My business does just fine on VIA and Amtrak.
The office is optimized for the present.
Which is exactly the problem.
If you’re a CEO, the present will consume you. Slack, decisions, people, noise… it all demands urgency. And urgency crowds out anything that isn’t immediate.
So a few times a year, I leave.
Not to a resort. Not to a conference.
I fly west… Saskatoon or Winnipeg… and then I take the train back to Toronto.
Two days. One or two nights. Cabin for one.
And I work.
---
The point isn’t the train. The point is what the train takes away.
No reliable internet for large stretches.
No meetings.
No one dropping by.
No ambient obligation to respond.
You can’t react… so you start to think.
There’s also something about movement. You’re going somewhere, even if slowly, and it creates a kind of psychological permission. Decisions feel less stuck. Ideas move. You move.
It’s hard to explain, but it’s consistent.
---
I’m alone most of the time.
That matters.
But not completely alone. Meals break it up. Conversations happen if you want them. At the end of the day, I’ll have a drink in the club car. Just enough social contact to stay human… not enough to derail the focus.
It’s a tuned environment. Not isolation for its own sake… isolation with relief valves.
---
I started doing this after reading about Bill Gates taking “reading weeks.” The idea stuck. You need time apart to deal with things that aren’t urgent.
At the time, I used these trips to clear backlog. Writing, mostly. Things I owed but never got to because the office only ever gives you “now.”
That problem is basically gone. AI took it.
The writing backlog doesn’t build anymore.
But the thinking problem didn’t go anywhere.
If anything, it’s more obvious now. Once the mechanical work disappears, what’s left is the part only you can do. Deciding what matters. Figuring out what to do next.
That’s what the train is for.
---
I think this is a bit of a boss move.
Most CEOs signal importance by being available. Always on. Always responsive.
I do the opposite.
I disappear… on purpose… on a schedule.
And the business survives just fine.
Better, actually.
---
It’s getting harder to book a cabin on VIA Rail now, which is interesting in itself. So I’m experimenting.
Next trip I’m flying to New York and taking the Silver Meteor down to Miami.
It’s not as nice. Food’s worse. The experience isn’t the same.
But I’ll have more connectivity… and for this particular trip, that helps. What I’m working through benefits from some input.
The platform changes. The principle doesn’t.
---
I don’t take the train to travel.
I take it to think.
Everything else is just logistics.
I love this framing of train travel. The idea about subtracting noise from modern life. Modern work environments are engineered for immediacy, but not for clarity. When you remove the constant inputs, what’s left is the part that matters most; the thinking.
I especially like the “tuned isolation” concept. The train offers enough solitude to go deep, but with small opportunities to stay human. Meals. The club car. That balance feels right.
The point about leadership resonates as well. The CEOs who need to be constantly visible and build companies built on 'cults of personality' are not durable. Stepping away, be it deliberately or regularly, signals a kind of confidence. You have built a sustainable system that works without you hovering over it.
Also, there’s something to be said for the analog nature of train travel. Slow movement, limited connectivity. It creates space in a way that no productivity hack really can.
Interestingly the First Person Essay published in this week's Globe & Mail is very much grounded in these ideas about the power of train travel -- "Still, suspended between destinations, between two worlds with all their demands, structures and stimulations, the train car feels like no place at all. It grants silence, anonymity and time to just be".