I just returned from my annual guys’ trip to the Boundary Waters. Although I’ve done this trip twice, I didn’t know exactly what to expect. There were two new people joining us, we changed some of our usual plans, and all of this was taking place during an especially busy chapter at Ei.

Still, I knew I had to go. The third time doing anything is special (see lesson #29 here). It becomes a tradition. A level of comfort begins to emerge. It’s not easy, but it is easier.

As usual, the trip was chock full of life lessons, but one stood out:

Discomfort precedes comfort.

A Worthwhile Challenge

This is a challenging trip in nearly every way. The packs are 50-60lbs, the canoes add another 40-50lbs. Unloading and reloading canoes is a dance of lifting and situating all of this weight onto each of the seven guys. Then, we carry those items (also known as “portage”) through elevation, rocks, roots, mud, and bugs. You’re hiking all of this in wet shoes because the edges of the water are simply unavoidable. When you’re paddling, you could face impossibly narrow streams, beaver dams, scorching sun, or winds so strong your boat turns sideways. There is no signage for the routes and no technology. You simply read a paper map and follow the route you set to complete.

And there is no “pre-booking” of campsites. You may aim for a specific site, but if it’s taken, you have to paddle to another. And maybe another. When you arrive, you spend 1-2 hours creating a home. Tents, kitchen area, covered area for seating, bear line for the food bag (which must be hung 12ft off the ground). Then, it’s time to find and cut firewood, unpack food, maybe fit in some quick fishing, and prepare the next meal. Finally, dip your water bottle in the lake and spend a few minutes filtering (it’ll still be yellow).

We did 13 miles of this on day one. Seven hours straight. In windy, gloomy conditions, we landed on the edge of Canada. Throughout the trip, we switched campsites three times, going even deeper into Canada and further from home. We were sore, tired, and spent. And yet, we laughed, played, swam, cooked, and had fun. Even with all of that work and discomfort, we felt a great sense of accomplishment. The group became a crew. Any comforts of home were long gone. The moment we entered the Boundary Waters Canoe Area Wilderness (BWCA), a new measure of “comfort” emerged.

To be honest, there were moments I hated — cursing that I’d chosen to do THIS as a vacation. But, just like prior years, there was so much beauty, so much accomplishment, such good company, and such a drastically different view of the world that I learned to love it all over again. (Aside from the mosquitoes. I hate mosquitoes).

This was the first time I left the Boundary Waters with no injuries or ailments. Aside from a few bug bites, I feel the same as if I’d gone to Cancun (okay, maybe a bit sorer). It’s the most comfortable I’ve felt after a trip of this intensity.

Discomfort in Life & Work

On the way home, I learned of Michael Easter’s work and his book, The Comfort Crisis. He writes about how comfort is a driving motivation for humans, and yet, for most of our existence, we’ve been hunters and gatherers — creating our own food, clothing, and shelter. Over the past century, our comforts have increased at such a rapid pace that our brains are still adapting and redefining resilience, endurance, and growth. It’s a complex challenge because comfort isn’t a universal concept and the same levels of comfort aren’t accessible to everyone.

Still, he advocates for incorporating more physical and psychological challenges into our lives — in appropriate doses for each type of person.

What’s the right amount?

It’s no secret that the past few years have already added a great number of challenges to life and work. Loneliness, burnout, uncertainty, political divide, war — how much more discomfort can any of us handle?!

I don’t have a clear answer. But I do believe one thing we can infuse into our lives, teams, and companies is a greater sense of agency.

When someone chooses a challenge rooted in a curiosity, passion, or deep interest — and they understand the possible reward — challenges are reframed as opportunities. We can help one another see opportunities for growth, connection, new perspectives, and even joy.

This is why I’m so excited for 2024 — a Leap Year. Helping people see where they want to make a shift and try something new (small or big) has never been more crucial.

They may not carry a canoe and pack, but they might see themselves and their world in a new light.