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September 14, 2018 General

Business Lessons Learned While Hiking

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By Theresa Conway

I’ve spent a lot of time in the Adirondacks over the past decade.  This past year, I continued my quest to hike all forty-six High Peaks in the Adirondack State Park of New York.  My last hike was a much-needed and long-anticipated clarity break with my family.  During the long and arduous hours on the trails, I learned many lessons that apply to my daily life at work.

Lesson #1: You’re going to catch a lot of spiders.

The trailheads of the High Peaks always start off in the trees.  The first person, who leads the morning hike on the trail, will run into all the little spider webs that were spun during the night – many at face level!  When hiking with my family, I usually hike in the lead to set the pace and clear these spider webs.  While I’m not particularly afraid of spiders, the feeling of spider webs on my face and arms is a little disconcerting.  This serves as a constant reminder that I am the first person on the trail that day.

The lesson I learned from catching these spider webs is that company leaders will always run into obstacles or complications that must be cleared for others.  This is especially true for growing companies encountering obstacles for the first time. Just because you’re catching spiders doesn’t mean that you abandon the hike.

Lesson #2: If you’re too focused on the trail, you will lose sight of where you’re going.

There are twenty trails in the Adirondacks called trailless peaks.  These trails were created by decades of hikers paving the way, but they are not maintained and have no markers.  The conditions of these trails are often muddy and eroded, and full of rocks and roots. 

To navigate safely, you often have to stare down at the spot where your hiking boot will next land.  In the autumn, after the leaves have fallen and covered the trail, trailless peaks are especially difficult to navigate.  If you’re too focused on where to step next, you will lose sight of where the trail is heading and end up off trail.  You then have to undertake the careful and unsettling task of navigating back to where you last saw the trail to get back on track.

The lesson I learned from hiking trailless peaks is that while it is important to focus on the day-to-day operations or weekly scorecard metrics of a company, it’s equally important to step back and make sure you are achieving your long-term strategic goals. When your goals are right for your company, they will keep you on the trail and lead you to your destination.

Lesson #3: Follow the cairns.

Cairns are piles of small rocks on bare summits or trailless peaks that were built by stewards and previous hikers to mark the trails.  This summer, I encountered a rubble slide on one of my climbs, and it was the carefully placed cairns that helped me find the best footing to safely make it up the incline.  Absent these cairns, I would have struggled to find a safe trail that avoided the precarious loose rocks of the rubble slide.

I’ve always known that I’m on the right trail by following the cairns.  A few years ago, as I was ascending the backside of Mt. Marcy, the highest peak in New York State, the evenly spaced cairns allowed me to stop and catch my breath in a cadence that carried me to the top of the mountain.  I have a small cairn in my office that reminds me of these trails and nudges me to find cairns in my daily life that keep on the trail that I navigate every day.

The lesson I learned from following the cairns is to look for guidance from those that have encountered similar business situations in the past. Here are four “cairns” I can recommend:


I have many more trails to hike and many more lessons to learn.  Hope to see you on the trails!

Photographs by Theresa Conway. Taken with iPhone 7 Plus.

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Theresa Conway

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