Jim, I’m thinking of paddling the Yukon River this summer. Any interest?”
Steve Myhill-Jones, who recently sold his company Latitude Geographics, is one of the most disciplined and methodical people I know. When he says he’s thinking of something, it really means he’s pretty much planned it out. I said yes right away.
With the addition of our friends (and local tech sector all-around good guys) Scott Lake and Brad Williams, the eight-day, 320-kilometre canoe trip north from Whitehorse to the Village of Carmacks promised to be worthy of its own Robert Service poem.
And yet, the most surprising and lasting impact of the trip was not so much the adventure itself, but the lessons we uncovered on the river and around the campfire. Lessons not just about what it means to have a successful and meaningful trip (which we most certainly did), but about business and life.
By day three I was collecting metaphors and insights that simply appeared to us on the river unannounced. With long days on the river and a sun that barely set at midnight, our extended conversations illuminated both our juvenile wit (hey, it was four guys in the middle of nowhere) and our natural impulse to find meaning in the mistakes we made and the minor hardships we overcame each day.
Of course, “What happens on the river stays on the river.” Nonetheless, here are a few notes I collected, with input from my travelling companions, to consider as your paddle your own way in business and in life.
Go all in.
Once we started, there was no turning back. We could not go back up the river and we couldn’t get plucked out partway. We had to finish no matter what.
Business Lesson: One can argue whether having a Plan B when starting a business shows a lack of commitment or appropriate risk mitigation. The way we see it, business is a river trip, not a lake trip: If you’re in, you’re in.
The best maps keep it simple and clear.
We had a GPS. We had detailed topographical maps. But the source we relied on for most of our daily decisions was a hand-drawn map. It wasn’t to scale, and it missed a few key features, but on a swift-moving river with three other guys asking for a quick decision on where to go, it communicated what was needed without extraneous information. Brad was especially gifted at reading the map and making the right call.
Business Lesson: The hand-drawn map reminded us of the great pitch decks and strategy meetings we’d observed throughout our careers in business. Succinct and to the point, it helped us get to a decision quickly and confidently.

Time does not equal experience.
Steve had far more years paddling than me. But I had a cheat code: As a kid, I learned to paddle an incredibly efficient stroke from people who had been taught by the legendary Omer Stringer (look him up). To my fellow Yukon paddlers, it looked like I was barely paddling. And yet my canoe was consistently quick. It was a bit of a revelation to us all: Time spent paddling does not equal better performance; learning to paddle correctly does.
Business Lesson: Entrepreneurs who learned early on the right way to do things usually outperform those with years of building companies on imperfect practices.
Make your own view.
Most of our campsites were on gravel bars with stunning views. But one day we found ourselves on a high bank overgrown with bushes. “No view!” we complained to no one but ourselves for the better part of an hour, until finally Scott made the call: “Guys, make your own view.” And so, armed with the vintage Western W49 Bowie knives Scott had given us, we went to work. Twenty minutes later, we — and every camper to follow that summer — had a better view of the river.
Business Lesson: So often we complain about something — a job, a boss, a competitor impeding our progress — that we forget it’s completely in our control to fix it. Don’t like what you see? Make your own view.
What’s your grizzly bear?
There are bears in the Yukon. Lots of them. And sometimes that stops people from going there. But it didn’t stop us. With Steve’s guidance, we took precautions (sealing food and carrying bear spray) and understood the risks. In the end, we didn’t see a single bear — not even when Steve and I hiked up a mountain covered with bear poop. But irrational fears can cause you to miss out along the way or not even start on a journey in the first place.
Business Lesson: Often they are just stories we tell ourselves — the “grizzly bears” of starting a business. Are they real? Sure. But don’t let them stop you from starting. Chances are you won’t see one. And if you do, that’s what bear spray is for.
The best weather report is opening your tent and looking outside.
We checked regional weather forecasts every so often via satellite phone. To be honest, they were pretty inaccurate. One or two valleys could make all the difference, and the reports just weren’t that precise. Soon enough, we learned to gauge our decisions against cloud movement well enough that we always made camp before any rain came. And often it didn’t come, even though it was called for.
Business Lesson: In business, people sometimes make decisions based on factors like sector trends or macroeconomic forecasts. But be careful of low accuracy/low precision datasets. Usually, it’s far more important — and helpful — to just look at what’s happening around you.
Don’t confuse luck with skill
We hit historic Lake Laberge on day two. It’s a 50-kilometre, two-day grind with the potential for high winds and deadly waves. Some years earlier, the lake had battered Steve’s trip. This year it was like glass for the two days we spent on it. Three hours after we left the lake, the wind picked up and battered those in the legendary Yukon River Quest who were following us, forcing some to drop out of the race. Clearing Lake Laberge with perfect weather had nothing to do with our abilities. It was luck. Moreover, it would be foolish for us to have any heightened confidence to tackle it in the future based on that experience.
Business lesson: In business, success is about timing, luck and — no matter the conditions — determination. Don’t tell yourself any different, or you’ll find yourself soaking wet.
Design the trip that suits you.
Want to paddle 700 kilometres from Whitehorse to Dawson City in 52 hours? Go for it. But you’ll hallucinate and have to pee in the canoe. Want to drink wine by a fire and eat Scott’s fresh-made naan bread at a beautiful campsite? Then do what we did, but don’t feel intimidated or “less than” when the Yukon River Questers go by.
Business lesson: Like paddling the Yukon, entrepreneurship is not just one thing. It’s whatever you need it to be. So what do you want?
Jim Hayhurst is a trusted advisor to purpose-driven organizations and leaders. He is currently active in six companies and social impact projects that elevate Victoria’s reputation as a hub of innovation, collaboration and big thinking.