Why the leaders who excel, don’t know the route, but they know how to read the conditions.
I have been writing the same book for six years.
That sentence is a little embarrassing to type, so let me be more precise about it. I have been writing a book for six years. It has been three completely different books in that time, and the one I’m finishing now (out in early 2027) is one I could not have described to you at the start, even if you’d held a pen to my hand.
Version one was about one-degree shifts. Small, deliberate moves that compound over time.
I still believe in the idea; it survived into the final book. But as I got close, I realized I had a mechanism with no problem attached to it. A beautiful tool, sitting on a workbench, solving nothing in particular. You can’t build a book on an answer that has no question.
So I started over. Version two was about authenticity. A real thesis this time, with something to say.
But the closer I got, the more I felt it pulling me off my own ground. It was a departure from what I’m known for that was just too drastic to commit to. The direction I actually wanted to move was toward more credibility and depth in the space I’ve spent a decade in: the future of work, how teams navigate uncertainty. Authenticity, for me, pointed somewhere else. So I let it go too.
Two false starts. Years of work, twice set aside. From the outside, it looks like someone who couldn’t make up his mind.
It wasn’t. It was something I didn’t have a name for until I read about a Harvard professor and a boat full of explorers.
The professor and the explorers
Linda Hill, who wrote Collective Genius, was stuck on the epilogue of her book. She and her team had rewritten it more times than they could count. Then one day she was reading about the explorers who first crossed the open ocean — the ones with no maps, no GPS, no satellite imagery. Just stars, currents, the moon, and a sense of where they were trying to go.
And she realized something the modern world had quietly forgotten. The leader we keep asking for; the one who stands at the front of the room and lays out the path, step one, step two, step three, follow me — made sense in a world where the path was knowable. A world where the future looked roughly like the past.
We don’t live there anymore. And the leaders we need now aren’t pathfinders. They’re Wayfinders.
Pathfinder vs. Wayfinder
A pathfinder knows the route. A Wayfinder knows how to read the conditions: the currents, the weather, the tools on hand, the people in the boat. A Wayfinder can’t tell you exactly which way the journey goes. But they know how to navigate whatever shows up. Wayfinders still plan. They simply treat plans as hypotheses rather than promises. They prepare rigorously, but they expect reality to teach them something the plan couldn’t anticipate.
It’s a small shift with enormous consequences:
- Pathfinders give answers. Wayfinders ask better questions.
- Pathfinders sell certainty. Wayfinders build the capacity to keep moving when certainty isn’t on offer.
- Pathfinders take you to the future. Wayfinders co-create it with you.
Here’s what I finally understood about my own six years. I thought I’d been failing to find the route. I hadn’t. I’d been Wayfinding the whole time and not realizing it was a method rather than a mess.
My direction never moved. It was fixed from the start: build something credible and useful in the space I’m known for. What kept moving was the destination, the actual thesis of the book. One-degree shifts. Authenticity. (Un)certainty. Each version was a course-correction, and the test I applied each time wasn’t “is this a good idea?” It was “Does this move me along my direction, or off it?”
Authenticity was a good idea. It just pointed off my line. A pathfinder, committed to the map, would have marched straight into a book about a topic that wasn’t his to own. The Wayfinder kept the direction and let the destination reveal itself.
And nothing was wasted. That’s the part that matters. The one-degree shifts from version one didn’t die, but rather, they became a load-bearing piece of the final framework. A wrong turn still illuminates. There is no such thing as a wasted move on the water; there are only moves that taught you something and moves you haven’t made yet.
“Anyone who tells you they know what the future looks like, doesn’t. Stop following pathfinders. Become one who reads the conditions.”
What changes on Monday
If you lead a team right now, three things shift.
- Stop pretending to know things you don’t. The team can tell. The credibility you think you’re protecting is the credibility you’re spending.
- Replace “here’s the plan” with “here’s the direction, let’s figure out the next step together.” That is not weakness. That is the entire skill.
- Spend less time perfecting the strategy deck and more time building the team’s ability to read conditions. Your job is no longer the map. Your job is the compass.
And if you’re not leading a team, if you’re just trying to navigate your own life, the same shift applies. Stop demanding a five-year plan from yourself. Nobody knows what five years out looks like, and the certainty you’re trying to manufacture is fake. Get good at reading where you are. Get good at the next move. The journey gets built one wayfinding decision at a time.
I know this works because I lived it the long way around. I didn’t plan my way to this book; I navigated to it, keeping the direction fixed and letting two destinations go when the conditions told me to. The book about why you can’t pre-plan your way through a changing world could not, it turns out, be pre-planned. It had to be wayfound.
Stop following pathfinders. Become a Wayfinder
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