Five Leadership Lessons from Finishing the Appalachian Trail

Thousands of people from around the globe start each year. Less than ten percent have ever finished. 

It was 7:52am. I rounded the corner, sprinting with every ounce of energy left only to see his burnt orange pack turning away to begin the journey, leaving me behind. It looked as if I was too late.

Earlier That Morning

After months of waiting, Tyler called and had set his finish date: August 5, at Mount Katahdin in Baxter State Park, Maine. It is the northern terminus of the Appalachian Trail. I booked my plane tickets to come straight from a business meeting in Canada to Bangor, Maine.

It was Friday morning, August 5. My wife, Jessica, and I set our alarms for shortly after 4am, threw on our hiking gear and started off. We stopped at a gas station in the last town to stock up with plenty of water and snacks.

We had awaited this day since March 18 when my younger brother, Tyler, set off on a nearly 2,200 mile expedition through over fourteen states—the Appalachian Trail. Each spring, thousands of people say their goodbyes to loved ones at Springer Mountain in Georgia. They turn to the trail for a five-month journey through woods and mountains, streams and boulders, fields and rivers. With a fifty-pound pack strapped to their back and hiking poles gripped tight, they embark on the adventure of a lifetime.

Day after day we waited for updates on progress. Sometimes just a few days would pass between phone calls or at the very least, texts. Sometimes it was weeks. Throughout the 141-day journey, Tyler shared desciprtions and photos of God’s incredible creation, stories of crazy hikers with absurd trail names, adventures while hitchhiking into rural towns and feats of the human body surviving the wilderness. He avoided wildfires, woke up to mice on his tent, conquered thirty-three mile days, learned what it was to be starving, stared a bear right in the eyes, scaled down the side of waterfalls, nearly tripped on a rattlesnake oh and not to mention survived walking 2,200 miles through snow, rain, wind, altitude, bogs and heat.

The Rendezvous

As we entered Baxter State Park, we were hoping, praying that Tyler would be at his rendezvous point. We had not spoken for some time. We told him, during our last conversation that we would arrive between 6:45am and 7:00am at his campsite so we could hike the last 10.4 miles of the trail with him and watch him summit Mount Katahdin. If we did not arrive by 7:45am Tyler was to begin his hike alone. Our contingency plan was to meet Tyler in the mid-afternoon at the bottom of the mountain.

Our GPS had us arriving at 6:30am. Plenty of time to meet up with Tyler. Turn after turn, our signal got weaker and weaker until it read “No Signal.” We had just turned down an unkempt, gravel road. The GPS had us turning away from the signs that I was confident were the signs we were supposed to follow. I had looked on Google and Apple Maps. Surely both were not wrong.

It had been a mile or two since I had seen any sign markers. I grew increasingly anxious. I took our rental car and began speeding down the gravel road, dodging pothole after pothole and trying to maintain some semblance of traction. 

We were just minutes before our estimated arrival time when I saw a sign for the AT. Phew! I pulled in and realized there was nowhere to park. This did not seem right. I had reserved a parking pass in advance with a clear description of the lot. This was definitely not it.

I quickly thrust the car in reverse to retrace our steps. About a quarter mile down the road, there was a middle-aged-woman in a faded, blue t-shirt smoking a cigarette. We rolled down the window, “Where is Katahdin Stream Campground?” I shouted out the open window. She kindly pointed us to the direction of the trailhead I had just attempted to drive a car down. 

“Where do I register for parking?” I asked with an inkling I was in the wrong place. 

“Oh, anywhere will be fine. There is a gravel lot down there where people park to hike,” she explained.

“So how far to the campground?” I inquired.

“A couple miles or so.”

At this point, we knew we were not in the right spot. We were supposed to be parking at the campground, not miles from it. Our options: 1) turn around and drive as fast as possible back down the rugged gravel road retracing our steps with hope to make it on time; or 2) hike to the campsite on the AT trailhead we had accidentally stumbled upon. Well, the one thing that we knew for certain was that we were on the trail and the trail most certainly led to Tyler’s campsite. We decided to park. We started to hike. 

About twenty minutes into our hike, we saw a brown sign with white lettering that said the Katahdin Stream Campground. On one hand, I was relieved. On the other, I panicked. We were still just shy of five miles away. We had just an hour until our worst-case-scenario rendezvous time. I was not going to let Tyler start his climb without us. He had to know we were there for him. I turned to Jessica and I knew the only way I could make it through over a thousand feet in elevation change, forest, streams, bogs and rock, was to run. Wow, I knew I was going to have to run part of the AT. We kissed goodbye, I gave Jessica the bag with food and water, and I ran. I ran fast.

Of course, my run started straight uphill on rock. Poor timing. When I reached the top, there was a split in the trail. I texted Jessica praying she would get the text to go right and follow the blue blazes. The brush became thick and the terrain, difficult. I was hopping from rock to rock, lunging to grab the next tree for balance. More than once, I was panicked that I had not seen a blue blaze marking my path. I quickly learned the whole AT was not actually a trail but a series of markers or “blazes” you had to look for yards ahead to know generally where you were going. Through leaping and sliding and jumping and running I quickly realized the human body has amazing traction, agility, balance and speed when faced against tough deadlines.

It was about 7:15am. On normal terrain,  I would have arrived at or been close to my destination. The end was nowhere in sight. I kept pushing along.

Finally, I heard a stream. Could this be Katahdin Stream? I wondered to myself.

It was not. I had less than fifteen minutes.

The End (Not) in Sight

I was praying. Oh so hard I was praying. My legs had not moved so quickly nor had my body encountered such varying terrain at such a high pace...ever. My feet were aching with the thud of every landing as I jumped from rocks and over roots. Slipping down slopes and pulling myself up inclines. I was praying Jessica would be safe. I was pleading she would find her way. I was praying Tyler wouldn’t leave. I was pleading that time would slow and I would speed up. I was praying I wouldn’t collapse. I was pleading that Tyler would just wait. I was praying.

With ten minutes left until the rapidly approaching 7:45am deadline, the ground began to flatten out. Well, relatively speaking. There were still ups and downs and all arounds, just less roots and more padded with pine straw. I promised myself that with every ounce in my body I would run full speed ahead, up and down, side-to-side until the timer ran out. Running full speed for ten minutes couldn't be that bad. The campsite had to be closer than that. My mind argued with my body. I was not set-up for success. I had not had my morning coffee, no breakfast and no water on me. I ran. I ran. I ran so hard.

With almost no energy left, I glanced down at my watch, 7:45am. I slowed down. Was it too late? I feared the worst. But I could not turn around, so I walked quickly, with the only energy I thought I had left. I felt defeated, but I pressed on.

Then I saw what appeared to be a trailhead through the thick pines. Maybe I was close. Maybe I could catch him. My walking pace lasted no longer than forty-five seconds before my adrenaline overpowered my legs and I broke out into a full sprint. I was past running on fumes, this was truly and act of God.

I happened upon the sign. It was a trail sign. An official AT sign. It was an arrow pointing left to Katahdin Stream Campground. It was just a quarter mile away. The trail turned into road. It was so much easier to run on. I pressed on.

I ran and ran. I saw campsites. Human life! Tents were still set-up, there was hope. I ran through the camp but he was not there. I kept running down the trail, around bends. He was not there. It was 7:51am. Scenarios were playing through my brain, I was close enough to the mountain that I could have run up behind Tyler to catch him. Seven minutes wasn't too far of a head start, was it?

The Corner

I was sprinting. I rounded the last corner in the campground. I thought I saw that burnt orange pack. Hope! Two football fields away. With every square inch of oxygen in my lungs I mustered to shout, “Tyler!” He did not turn around. Maybe it was not him. I ran harder. One football field away.

Then, all of a sudden, at 7:52am, I saw him. I saw my brother, with pack strapped on, ready to go. He was leaving. He did not see me. His hiking partner, Chris, saw me. He pointed. Tyler whirled around. Success!

He started walking towards me, dropped his hiking poles, opened his arms and I ran right into them. I got all choked up and began to cry. Two grown men, beside ourselves, with tears of sweet reunion. I had made it. Tyler had made it. Here we both were, at our own finish lines. We had made it.

I have never been more proud in my life. To see my little brother all scruffy-bearded with shaggy long hair and more stinky than ever about to finish his lifelong dream made me sob with tears of joy, of pride, of love. The hikers funk--a common descriptor for the soured-milk/B.O. smell wafting from thru-hikers--could not keep us from an incredible embrace and sweet reunion. Writing this on the plane back, I’m crying. This was better than any graduation or any awards ceremony. This was truly once in a lifetime. It was once in a million. 

After a couple minutes of conversation, hugs, tears and pictures, we decided that he should go on his way to hike Katahdin without Jessica and me. It wasn’t the original plan, but plans change. I got to see my brother. I got to watch him walk off to finish his dream. I let him know we would have an air-conditioned car at the right campsite by the time he would finish. I wished him well as he turned to do the last ten plus miles of the trail he had been hiking for 2,200 miles over 141 days.

Five Leadership Lessons from the Appalachian Trail 

The trail embodies so many key qualities you see in a successful business leader. The odds of finishing the trail successfully are far more slim than being successful in business, yet the lessons can be applied in both places. Tyler's courage, bravery and passion left me with five incredible lessons. 

• Tyler had vision. After reading a book, he knew he was going to hike the trail in its entirety.
• Tyler had focus. So many incredible career-changing opportunities came up, time and time again. In fact, more opportunities than I’ve seen for anyone else. He knew he was going to hike the trail so he turned each one down as he focused on his goal.
• Tyler had drive and determination. Time after time, people told Tyler he was crazy for turning down opportunities or to go live in the wilderness for five months. He had drive and determination, he was going to hike the trail. He did it with integrity. If he got off the trail at any point to go into town and grab food or visit with a friend in a nearby town, he made sure to start back exactly where he left off. He was determined to finish the trail in its entirety, no shortcuts.
• Tyler had perseverance. Getting on the trail is one thing. Heck, I got on the trail. Staying on the trail is another. Nearly fifty percent of all thru-hikers drop off in Virginia. By the end, only ten percent on a good year have made it the whole way. Through hunger and extreme weather, through unfathomable aches and pains, he made it. He never gave up. There were times he considered it, but he never gave up.
• Tyler had a running mate. If you have ever heard me present on leadership, you have heard me talk about a running mate. Every successful person has had a running mate. Tyler found his the first day on the trail, Chris. After a week or two, they decided to journey the rest of the way together, spurring one another on.

Words still do not seem to form when I try to recount the overwhelming emotion I felt embracing my brother after my run to him and then again after he took the last step on the trail, arms raised high touting his victory. Words cannot begin to scratch the surface of how proud I was to watch him sign a ceiling tile with his trail name at Appalachian Trail Café in Millinocket, ME as one of the few thru-hikers who made it. I was proud to share with a wine-maker during a wine tasting in Winterport, ME that my brother had just finished the trail the day prior. The 60-something winemaker’s response of respect, admiration and pride for my brother was indescribable. He started showing Tyler off. The pride was contagious.

There are not many feats in life with bragging right like finishing the entire Appalachian Trail. But let me say this: Tyler, I am so incredibly proud of you and I am proud of Chris, who you met along the way. I am glad you found each other early on in your journey and spurred each other on to one of the greatest physical, emotional, mental and spiritual challenges on this earth.