I sternly but supportively urged my friend Charles up the last crest of the Boston Marathon’s infamous Heartbreak Hill. My four colleagues and I surrounded him—two in front, two behind and me beside him, tethered by an 18-inch chain looped around my arm that Charles held while we ran. Adorned in neon green bibs that read “Caution Blind Runner,” we were a mobile phalanx with one mission: to help Charles get over the finish line of the 2009 Boston Marathon safe and sound.
I had met Charles because I serve on the Board of the New York Road Runners, organizers of the New York City Marathon, and through them I was introduced to the Achilles Track Club. Achilles helps physically challenged athletes compete in running events across the globe. Charles, a member of Achilles, had made up his mind to run a marathon; he just needed a team to assist in the effort. So four other volunteers and I started to prep with Charles for the big day.
I plan meticulously for marathons—I’ve run 26—but I know that something will go sideways at some point. It always does. Now I had a litany of new questions.
“How would we train?”
“How would we establish a comfortable pace?”
“Was special equipment needed?”
“How would bathroom breaks work?”
“Would I be warning him about every discarded banana peel, wet crushed cup and slick manhole cover?”
In thinking through this Rubik’s Cube-like puzzle, I was struck by how much it felt like entrepreneurship. Training for and running a marathon felt a lot like starting a company. In both cases, you experience:
• Intense Focus
• Teamwork
• Decision making with very little data
• Peaks
• Valleys
• Failures
• Wins
• Excitement
• Despair
• Pace
• Goal setting
• Active listening
• Strategy
• Adjustments
• Razor-sharp awareness
• Discipline
• Extra effort
• Doubts
• Dedication
• Perseverance
• Reality checks
• An ability to quash doubts
And, most importantly, the ability to deal with enormous uncertainty without panicking. Building a business, that uncertainly is part of your everyday reality. In running, I had learned to cope with it after watching runners pass out in front of me, having people puke on my shoes, realizing my toenails were falling off and being so hungry that I once picked up a squashed mini chocolate bar and ate it with the wrapper on.
The big difference between running a marathon and the entrepreneurial journey is that, in the latter, you don’t know where the finish line is, whereas in a marathon, no matter how many of them you run, seeing the finish line is exhilarating. You’re almost there! But Charles wouldn’t be able to see the finish line—and still, he was embracing the uncertainty.
After we crested Heartbreak Hill, Charles started to run out of gas. We had been on the course for over three and a half hours, and the temperature was dropping with the sun. The rolling hills that dot the last six miles of the Boston Marathon now felt like mountains. We encouraged Charles to keep his form and breathing regimen intact.
“Use your arms to get you up this hill—almost there. Slight left—there are cups 10 yards ahead. Gatorade station, 200 yards. Stay strong, stay strong.”
He nodded, but he had not responded to our words in two miles—he was too tired to talk. Uncertainty had set in, and panic would come if we didn’t do something.
Then, about 100 yards beyond the Gatorade station, I noticed a preppy guy in loafers with an old-school boom box at his feet. He noticed us too, and appeared struck by “Team Charles.” He fiddled with the boom box, and suddenly the theme from Rocky, “Gonna Fly Now,” was blaring. The crowd clapped and cheered. Charles pulled his head up and started to churn his arms like pistons as his breathing came together. Preppy Guy fell in stride with us and ran the last 3.5 miles in his loafers with his teal sweater tied around his waist. He DJ-ed the entire way: the theme from Chariots of Fire, “Eye of the Tiger” and, as we crossed the finish line, Kool and the Gang’s “Celebration.”
That was followed by lots of tears and hugs, and as the race organizers placed a medal around his neck, Charles asked everyone about the mysterious music man. “Was that guy on a bike?” Through the tears we roared with laughter and hugged Charles, Preppy Guy and each other. Panic never arrived. We did.
