Are you a +1?

There's a certain nostalgia that comes with revisiting a past passion. Just recently, I had the opportunity to experience it firsthand when I embarked on an expedition down some of Oregon's most renowned whitewater rivers. The adventure took me back to my early twenties when the pulse of whitewater kayaking dictated the rhythm of my life.

When I was in my early twenties, I lived in the pristine Mount Robson Valley, nestled in the Canadian Rockies. In this wilderness paradise, icy rivers, fuelled by glaciers, are bountiful. Enthusiastic kayakers can spend every summer day tackling challenging rapids, never feeling the sting of boredom.

My kayaking journey reached its climax when I became part owner of my own white water rafting company in a little town called Valemount. Anyone who has travelled there knows how special this little pocket of British Columbia is.

But owning the rafting company opened up a new passion: entrepreneurship. And although a seasonal rafting company can become a fantastic lifestyle business, my eyes began to settle on bigger goals. So I moved to Vancouver to start my next journey into various capitalist exploits.

For the last decade, I’d become estranged from my kayak, the paddling community and the white-knuckled, tight-chested emotion that comes with dropping into a steep piece of whitewater. It is a special feeling.

But last week, I rekindled that flame. Together with a group of old friends, we paddled the Clackamas River in southern Oregon, a class 3 run with some sporty class 4 drops, and the North Umpqua River, a river of similar temperament. This was followed by a three-night expedition down the Rogue River - one of America's most revered stretches of whitewater.

Returning to the river was like opening a time capsule from my past - the muscle memory in my hips as I carved down a rapid and the instinctive reaction to the chaos of hydrology. To the untrained eye, a big rapid often resembles disorder - a flurry of water rushing downstream. But to a seasoned paddler, there is order and patterns, an understanding of what features are dangerous, and where there is a clear passage.

What struck me most about revisiting this part of my life was the sense of companionship. I participate in many adventure sports - I mountain bike, trail run, ski and snowboard - all fun sports to do with friends. But while all of these sports offer a certain companionship, whitewater kayaking stands apart. When paddling a high-consequence river, you need more than good friends; you need people who have your back if things go south.

Unlike a mountain, a river, after a misstep, doesn't afford you a pause to catch your breath. It continues to push you downstream, relentlessly, posing the risk of being swept into log jams or underwater sieves. If problems arise, there is no option to take a minute to catch your breath. The force of a river is unforgiving, and we can’t breathe underwater.

At the risk of sounding overdramatic, whitewater rescues can quickly become body recoveries. When someone gets in trouble, the group needs to spring to action immediately.

This underscores the importance of having the right companions by your side. You need people who can take care of themselves, make intelligent decisions, and are ready to jump into rescue mode should one of their peers go down.

On the river, there is a system to help assess the competency of a group. Each member must self-identify as a +1, a -1 or a 1 relative to the river's difficulty.

A +1 is someone comfortable with the level of difficulty and will be competent to execute a rescue if needed.

A 1 believes they can care for themselves on the river and is not over their head in terms of challenge. However, they are at the upper end of their skill limit and should not be relied on for rescue.

A -1 is someone whose skill level will be seriously challenged by this river and must be shadowed by a stronger kayaker if they need a rescue.

The sum of these self-assessments should always be a positive number. Like any adventure sport, whitewater kayaking has unavoidable inherent risks; the goal is to limit exposure to these risks as much as possible.

Early in my kayaking career, I was often the -1. I was full of ambition but green in experience. I would often join groups that had been running rivers for much longer than I had. As my skill grew, I started finding myself in the “1” group and eventually in the “+1” group.

Pondering this system last week while on the river, I was struck by how I have integrated similar concepts into my life beyond kayaking.

As an entrepreneur, I surround myself with disciplined, big-picture thinkers who lack a capped mindset about their capabilities. There is always a mix of mentoring and mentorship - anyone who has ever educated or mentored someone understands that teachers often learn as much as students.

My self-identified score shifts as I migrate through the facets of business - I may be a “+1” if we discuss product development, but a “-1” in administration processes. I have a lot to offer and a lot to learn.

As an investor, my conversations gravitate toward those with more significant accomplishments, superior deal flow, and greater financial success. To stress-test a hypothesis about where I want to deploy capital, the most effective strategy is to elucidate it to another person. The process of instructing someone else about my convictions invariably exposes my blind spots.

Social relationships, too, are an energy exchange. Individuals can either inject me with inspiration, ambition, and a competitive mindset, or they can deplete my positivity, quell my motivation, or—most detrimentally—lower my performance standards. However, like entrepreneurship, this dynamic isn't binary - those who require my assistance today may provide the guidance I need tomorrow.

In my friendships, I gravitate towards energetic adventurers who relentlessly seek personal growth and challenge, who crave unique experiences, and who uphold high integrity and aspirational character.

Over the years, I've distilled a few guiding principles to help me manage relationships:

1. The richness of life correlates directly with my willingness to engage in difficult conversations. It's worthwhile to frequently revisit this question: Is this relationship more important than my goals? A word of advice - it doesn't make me a villain if the answer is no.

2. If I find myself repeatedly contemplating whether or not to maintain a relationship, the answer is usually no.

3. The most rewarding relationships are those where both parties feel they are getting the better end of the deal. Pursue win-win situations.

4. Although being the expert is gratifying, being the novice is more advantageous. If I look around the table and realize I'm the least experienced person present, then I'm usually in the right room.

5. Like the river, life presses forward whether we are ready or not. Put your paddle in the water and take control...

Keep reading with a 7-day free trial

Subscribe to Jay’s Letter to keep reading this post and get 7 days of free access to the full post archives.

Start trial

A subscription gets you:

	The Deep Dive - The Most Important Signals in Business, Finance and Culture.
	Portfolio Allocation and Rationale
	The Sovereign Life Blue Print