Friday Leadership Report | Alan Kearns, Founder & Managing Partner, CareerJoy
Happy Friday,
This past week, I listened to an interview on CBC with an author who studies famous sayings and how their meaning drifts over time. You know the kind of thing. A line gets lifted out of its setting, polished by a thousand graduation speeches and coffee mugs, and a few generations later it means something close to the opposite of what the writer intended.
Then he got to Robert Frost, and I pulled the car over. Well, not literally. But I did listen to it twice.
We all know the line. “Two roads diverged in a wood, and I, I took the one less travelled by, and that has made all the difference.” It has become the anthem of the bold decision. The entrepreneur who walks away from the pension. The executive who ignores the consultants and bets on her gut.
Be different. Don’t follow the crowd. Take the road less travelled.
Except that is not what the poem says.
Go back and read the middle of the poem slowly. Frost tells us the two paths had worn “really about the same.” He tells us that both that morning “equally lay in leaves no step had trodden black.” Neither road was the popular one. Neither was the brave one. A man stood in a yellow wood, looked down two paths that were, for all practical purposes, identical, and not knowing where either led, he chose one.
That changes everything.
The “difference” in the final verse isn’t about the road at all. It’s about the story. Frost tells us he’ll tell this “with a sigh, somewhere ages and ages hence.” Years from now, he will describe his road as the one less travelled, even though he knows, standing there in the leaves, that it wasn’t true.
And notice the title. It isn’t “The Road Less Travelled.” It is “The Road Not Taken.” The heart of the poem is the path he didn’t choose.
I can picture him. He is older now, settled into a comfortable chair, grandkids spilling across the living room floor. A good life. A very ordinary, very full life. And somewhere in the middle of the noise, his mind drifts back to that morning in the woods, and he wonders what might have been down the other path. He sighs.
I think that sigh is one of the most honest things ever written about leadership.
Here is where I want to be careful, because there is a trap on both sides.
For years we have been told that real leaders take the road less travelled. That conformity is the enemy of greatness. There’s truth in that. Some of the best leaders I have coached over nearly thirty years were people who saw what others missed and had the courage to act.
But I have also sat across the table from leaders who chose the unusual path mainly because it was unusual. They mistook contrarianism for vision. They needed to be seen as bold, and the organization paid for it.
The opposite trap is just as real. Following the crowd feels safe. If everyone else in your sector is restructuring, or buying, or cutting, or rolling out AI, it is tempting to do the same and call it prudence. Nobody gets fired for taking the well-worn road. Until they do.
Canadian leaders are standing at a lot of these forks right now. The EY Canada CEO Outlook for 2026 found that 62 percent of Canadian CEOs now intend to pursue mergers and acquisitions, up from 46 percent heading into January. That is a big shift in a few short months. PwC’s 2026 Canadian CEO Survey found that Canadian chief executives are significantly more likely than their global peers to have moved into new sectors over the last five years, while also being more worried than their global counterparts about whether their companies will remain viable in the medium to long term.
Read those two findings side by side and you see a country full of leaders making consequential choices in a fog. Some of them are joining a crowd. Some of them are striking out alone. And here is the real point of Frost’s poem, the one I think we have been missing for a hundred years.
Whether many people have gone that way or not is not the point.
What strikes me most about the traveller in the poem is his honesty in the moment. He doesn’t pretend to know. He looks as far down one path as he can see, to where it bends in the undergrowth, and that’s as far as anyone can see. Then he decides.
That is what most real leadership decisions feel like. We love to talk about decisions as if one option is clearly wise and the other clearly foolish. In my experience, the easy ones rarely make it to the leader’s desk. The ones that land there are the ones where both paths look about the same. Both are reasonable. Both have costs you can see and costs you can’t. Your team is split. The data points in two directions.
EY put it well in their outlook. Clarity may be elusive, but Canadian CEOs are moving forward anyway.
So what does good decision-making look like when the paths are equal? I think it looks like three honest admissions. I don’t know where this leads. I am choosing anyway. And I am choosing for reasons I can name out loud.
Those reasons matter far more than whether the road is crowded. Are you choosing this path because it fits who you are and what your organization is for? Or are you choosing it because it will look good in the story later?
This is the part of the poem that stopped me in my tracks. The traveller already knows, in the moment, that he’s going to embellish the story. He’s going to tell people he took the road less travelled. He is going to turn a coin flip into a legend.
Leaders do this all the time. I have done it. We make a decision with incomplete information; it works out, and a year later we describe it as vision. Or it doesn’t work out, and we describe the circumstances. Either way, we slowly rewrite the morning in the woods.
Why does that matter? Because the people who work for you were there in the woods with you. They remember that the paths looked the same. When you retell the story as a heroic certainty, something quiet breaks in the room.
When I look at Canada’s most trusted executive teams, I keep coming back to it. Employees at those organizations don’t expect their leaders to solve every crisis or predict the future. What they trust is that their leaders have their back and will face the hard things with them. That’s not a demand for perfect foresight. It’s a demand for honesty.
And the conditions for that kind of trust may be better than we think. The 2026 Proof Strategies CanTrust Index found that trust in each other and in key institutions is rising across Canada, a kind of Team Canada moment in a disrupted world. People are willing to extend trust. Leaders squander it when they narrate their decisions dishonestly afterward.
The leaders I admire most tell the story straight. We had two good options. We didn’t know which was better. We chose this one; here is why, and here is what we have learned since. That kind of storytelling doesn’t make the leader smaller. It makes the whole organization braver, because it gives everyone permission to decide without pretending.
At CareerJoy, we use [LQ] Leadership Intelligence with leaders across the public, private, and not-for-profit sectors. I raise it here because the question Frost leaves us with isn’t really about strategy. It’s about character. Can you make a hard call without certainty, own it without spin, and live with the road not taken without letting it haunt you or harden you?
That is not a skill you pick up in a weekend workshop. It is formed over years, in lots of small decisions, with people around you who tell you the truth.
It is also the question sitting at the centre of our Work. Made Better. 2026 Report. We are in the middle of interviews right now with Canadian organizations about how they develop leaders consistently, not just the occasional star, and I am already hearing how much of this comes down to the kind of honesty I have been describing. I’ll share more when the report comes out this fall.
This time of year, driving up to the cottage on Big Rideau Lake, the maples along the back roads start to turn. Every September it takes me by surprise. And every September I think of that line about two roads diverging in a yellow wood.
Here is what I hope for you this week. When you come to your own fork, and you will, don’t waste energy asking which road is more travelled. Ask which road you can walk with integrity. Choose it honestly. And when you tell the story years from now, in your own comfortable chair with your own grandkids underfoot, tell it true.
The sigh is allowed. It means you took your choices seriously. It means there was a real road not taken, and you were paying attention.
If you or your leadership team are standing at one of those forks right now, we’d love to walk it with you.
Along the road with you,
Alan
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