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A Lesson in Preparation and a Trail Race to Remember

I’m not what one would call a "runner". These days, I’m fortunate to live across the street from a forest—conservation land with a few hiking trails that serve as the grounds for sporadic runs with our 4-year old vizsla, and every once in a while, with my teenage daughter or preteen son.

The trails are fairly technical—running terminology that indicates rough terrain, specifically how likely you are to step on a rock or tree root (among other obstacles). I have to constantly watch and anticipate each foot fall. Failure to do so has led to quite a few stumbles, several rolled ankles and, admittedly, a handful of spills.

Like most runners, especially slow runners like me, I do a lot of thinking while plodding along. Some days I try to solve a family issue, others I ponder the dynamics of the baseball or basketball teams I coach, but often I think about my search business and our clients.

Some Historical Perspective

Between 2007 and 2010 I ran a marathon each year for four years straight and even then, I balked at calling myself a "marathoner". I reveled in the discipline it took to train for a marathon and enjoyed training with a few friends who were running their first marathons.

I wasn’t fast. To be clear, my goal was simply to finish the 26.2 miles and experience the rush of emotion that always accompanied crossing the finish line.

During the summer of 2011, while training for my 5th marathon, I had a Forrest Gump moment. I was in the middle of a 14-mile training run when I simply stopped. I was done. Maybe it was boredom. Perhaps I was tired. I could have been dehydrated. At that moment, I just knew that road running wasn’t doing it for me.

I called a friend who is an accomplished marathoner—she’d actually won one a few years back. Rather than push me to continue my marathon training, she encouraged me to pivot my training towards trail running. She and her husband had signed up for a 9.5-mile trail race in northern Massachusetts, near the New Hampshire border, and urged me to do the same.

For the next few weeks, I took to the local trails and genuinely enjoyed the experience.

The mental difference between trail running and road running, to me, is stark. Trail running is just more involved—watching every foot fall, using different muscles, engaging with your immediate surroundings. It also takes more time to cover the same distance as a road run.

The morning of the event, following an hour-long drive to the race site, I received a text saying that my friend’s husband was sick and that they had decided the skip the race so he could recover. I was disappointed but quickly realized that, to be fair, if either spouse had competed, I had no hope of keeping up with them. I had no illusions of us running side by side (or one behind the other), chatting amiably, while maintaining what was likely to be their 6 or 7-minute per mile pace. Truth be told, I figured we would say hello before the start and compare notes after the race, recognizing that that would finish well ahead of me.

Are You Equipped to Compete?

In early 2011, Christopher McDougall's book Born to Run was quickly becoming a National Bestseller. In its aftermath, road runners and trail runners alike began to experiment with barefoot or minimalist running—donning footwear that lacks cushioned heels, soles and arch support—basically running with very little between your feet and the road or trail surface.

As I joined the group of runners congregating near the starting line, I glanced at my competitors’ various footwear choices. For most, trail running shoes were evident–designed to protect feet on rugged terrain. There were quite a few runners with road running shoes—generally more lightweight than trail running sneakers. I also noticed a handful of competitors wearing the new Vibram FiveFingers—picture a glove for your foot—essentially a sock with a rubber sole with individual slots for each toe.

One runner stood out. He was clad in black–black bandanna, black sweat-wicking t-shirt, and black shorts. But what caught my eye was his choice of footwear. He was wearing black sandals akin to those worn by the fabled Tarahumara in McDougall's book. Picture an open-toed sandal or flip-flop, but with a sole about the thickness of a quarter (not a quarter inch, mind you, an actual 25-cent coin). It was uber thin.

We struck up a conversation during which he extolled to virtues of minimalist running. He’d been testing these sandals for a few weeks and swore by them.

I asked, "Have you run with them on trails? Have you run this trail before? Have you asked others that have run this trail about how technical the terrain is or isn’t?" Did he know what he was getting himself into? I sure didn't, but I was wearing trail sneakers. He more or less dismissed each question. "I'll be fine," he said, and with that we wished each other 'good luck' and readied ourselves for the start of the race.

Knowing When to Quit

Two miles into a nine-plus-mile trail race, I rolled my right ankle. It smarted something fierce. I was in the middle of the race pack on a single-track trail and politely moved aside to let other runners pass, including my new friend with the minimalist sandals.

Having let the bulk of the competitors through, I began to walk, then slowly jog, and when I felt up to it, I ran. Half a mile later I rolled the same ankle. I barked an expletive that may have been heard in Canada. It was definitely heard by the walkers behind me and at the water station about a tenth of a mile ahead of me.

After fielding several, "Are you OK?" questions from volunteers and competitors, I asked where we were located relative to the parking lot. My ankle was trashed, my confidence was shot and wanted to get in my car and go home. They explained that I could walk the two and a half miles back to the start or push forward about the same distance on the racecourse, where another trail would lead to the parking lot.

I chose to move forward, admonishing myself and cursing my luck as I trudged towards the trail that would lead me home.

Little by little, which each tentative step, each test of my fragile ankle, I began to feel better. If my foot found purchase on flat ground, if I avoided major rocks or roots, I felt OK. I half jogged, half walked for a bit and in time found a pace that allowed me to avoid the worst of the pain. When I reached the juncture to turn to the parking lot, located about halfway through the course, I pushed past it, believing that I could finish. I didn't want to throw in the towel.

In Hindsight, a Lesson Learned and the Reward for Perseverance

Eventually, I caught up to the walkers. Then the slow joggers. Then a few of the competitors who, like me, had some ailment that forced them to take it slower than they'd originally planned.

A few paces in front of the Mile 7 marker, after a few gnarly hills with jagged rocks and treacherous roots grabbing at the tips of my sneakers, I came upon my friend with the sandals. He was visibly limping and close to tears. His feet were a mess—dirty, bruised, and bloody. He was lamenting his choice of footwear and chiding himself for his lack of research and preparation.

I offered to help him make it to the finish line but he declined. After several attempts to help, he waived me on and encouraged me to finish my own race.

Two miles later I emerged from the forest and slowly ambled across the finish line. My time? No idea. Doesn’t matter. I was just grateful to have finished.

At the finishers' tent, to my surprise, I was handed two brown beer bottles. I noticed a few finishers cracking theirs open on the spot and went to do so myself. I figured I'd earned it. Turning the bottle to see the label, I didn't recognize the brand. No worries, any beer would have tasted great in the moment. But, upon closer inspection, I loudly grumbled, "ROOT BEER?" Who gives out root beer at the end of a race?

Hearing my outburst, a woman in what I estimated to be her 60s approached, held out a bottle of wine, and offered to trade with me. "I don’t drink wine, and besides," she said, "I really like root beer!" We exchanged bottles and when I glanced at the label, I realized that it read "Age Group Champion.” Not only had she handily beaten me in the race, but she also won her age group! This wasn’t just something they hand out to finishers; this was an honest to goodness award.

"I can’t possibly take this. You earned it," I pleaded. She assured me it was a good trade and seemed unphased by giving up the bottle. Maybe she’d won so many awards that she lacked space on her mantle? Maybe she really did love root beer? Regardless, I was touched by her kindness.

I quickly took a picture of the label and emailed it to three people without any accompanying comment: my friend who stayed home, my wife and my parents. My friend, who’d never run with me before, thus didn’t know how slow I really was, congratulated me on my accomplishment. My wife was stunned but also replied with her congratulations. My folks, knowing me as a bit of a prankster in my youth, were the only ones to question the validity of the award. After a few minutes, I came clean to each party we all had a good laugh at my expense.


I never saw my sandal-clad competitor finish the race and don't know what became of him. Did he find a path to the parking lot and peel off in frustration? Did he grit it out and finish? Afterwards, did he continue to run in his sandals or throw them away?

During my recent trail runs across the street, I've thought about him quite a bit while reflecting on the challenges of the executive search and asset management industries in our current environment.

  • Do we understand the race we're running?

  • Are we talking to the right people to gain knowledge of the course?

  • Are we offering guidance and advice to those who need our insight or want to use us as a sounding board?

  • Do we understand the basis of competition as it exists today and anticipate where it's headed?

  • Are we effectively training ourselves for what's to come?

  • Are we innovating and testing ideas that could give us an edge before implementing them?

  • Are we equipping ourselves with the right tools/products/solutions (the right footwear, so to speak) to compete effectively?

  • Are we watching our foot falls—aware of the obstacles that might trip us?

  • Or, are we winging it?

In Case You Were Wondering

It’s been almost 9 years since the trail race and I don't recall what happened to the wine bottle or its contents. I didn’t earn the award. It didn't belong with the salty bib numbers, finishers' medals and other race paraphernalia I've collected over the years.

But I do have the memories, the lessons learned…and the picture.

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