Chapter Thirteen — Michael Phelps

Plan B

Jeff Cunningham
6 min readMay 31, 2021

How humble upbringing and a freak accident inspired Olympian Michael Phelps and SAP CEO Bill McDermott to do great things.

Plutarch is the most famous biographer in history for a good reason. He was the first to write about great leaders like Julius Caesar by looking past his victories and probing into the smaller details of a big life. He wrote:

“For it is not histories, I am writing, but lives and the most glorious deeds do not always reveal the inner workings. Frequently, a small thing gives more insight into a person than battles where thousands fall.”

When we think about the enormous challenges facing leaders today, things like disruptive technology and geopolitical hysteria come to mind. We expect our leaders to rise to the occasion, and when they do, we celebrate and praise them.

But is that “end of story”?

In fact, by simply adding up the highlights of a leader’s life, have we really learned how to translate their unique talent into winning in our own lives? Our tendency to dwell on the peaks of a career — as if we are answering a multiple-choice test — causes us to miss the best parts.

Michael Phelps with 23 Olympic gold medals (photo: Sports Illustrated)

How many Olympic gold medals has Michael Phelps won?

1. 8

2. 29

3. 23

Phelps won his 23rd gold medal in the 2016 Olympic Games in Rio, the highest number of medals won by a factor of more than two of anyone in Olympic history. That record began over 2,100 years ago, by the way.

But each of Phelps’ medals deserves a story all its own. The significance isn’t that Phelps won 23 gold medals. It’s that on 23 separate occasions, he challenged the best competitor in the world and won.

Humble Beginnings

“The wildest colts make the best horses.” — Plutarch

SAP CEO Bill McDermott (photo: Business Insider)

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William R. “Bill” McDermott is the first American CEO of SAP, the global enterprise software firm. Previously, he was the youngest officer at Xerox. But long before those victories, he started a corner delicatessen in his hometown of Amityville, Long Island, at the age of 16, to pay his way through college.

SAP, as the world’s largest business software company, with over 85,200 employees and 350,000 customers in 180 countries, and $30 billion in revenue, makes McDermott one of the most successful executives of his generation. He is a well-known figure at Davos, at the White House, and in all corners of the earth where enterprise business is done. Although he makes it look easy, it was anything but.

“I grew up understanding that anything given or earned can be taken away. To this day, I truly believe I must keep proving myself. When you start to feel entitled, that’s when you start to slide.”

When McDermott was seven, his five-year-old brother died. Early in his career, he left Xerox to become president of Gartner Group, a leading IT consultancy. That same week his wife was diagnosed with breast cancer. Later, his mother died of pancreatic cancer. He was at her bedside when she told him to leave because he had to give a speech at Radio City Music Hall before an audience of 20,000. He returned to his mother’s side shortly before her death.

Michael Phelps was training for the Beijing Olympics in 2008 in Ann Arbor, Michigan, when he was trying to do something many of us do several times every day, get into a car.

It turns out the Olympian is a bit of a klutz.

“You should just keep me in the pool, put a bed in the pool, give me food in the pool so I never get hurt. I’m bad on land.”

He fell, bracing himself with his right hand, and broke his wrist. A broken wrist is a nuisance to most of us, but to a swimmer at Phelps’ level who wins races by hundredths of a second, it’s the wing flap to an airplane. You can’t swim competitively and win with a broken wrist.

Bob Bowman, Phelps’ coach since his early days of training, put a rose-tinted lens on it when he told the Detroit Free Press he was “not worried” and that the break “could have healed on its own.”

But media pundits were quick to catch on to the severity of the injury and thought it spelled disaster for Phelps. They predicted it would keep him out of the water and doubted not just that he could win but whether he would even qualify. “Will he even be able to compete in the Olympics at all?” the headlines blared.

Later, Bowman admitted Phelps was as upset as Bowman had ever seen him. “He was devastated,” Bowman said. “He kept saying, ‘It’s over. I’m finished.’”

Phelps knew he had to lay off swimming but still find a way to prepare. He let his natural competitive instinct take over and figured out a way to train without swimming. “I realized that all the people that told me I couldn’t do it, that this is going to make it even harder, you know what? I’m gonna do it.”

Phelps got back in the water using a kickboard, doing his laps using only his legs. Let’s call it the Phelps crawl because it helped him set a world record.

Fast forward to Beijing. Nine months later, Phelps faces incredible competition from Serbian gold medalist Milorad Cavic in the 100-meter fly. With less than one lap to finish, Phelps is a full stroke behind Cavic. That’s when Phelps kicks into high gear. His turbocharged kick was strong enough to get his hands to the wall first — and he won the gold by 1/100th of a second.

When the race was done, Bowman said, “The tremendous setback…without it, Michael would not have won the race.”

Michael Phelps agreed, and he also learned something about himself and life, when you overcome adversity, it becomes your friend:

“It made me realize that things can change in the blink of an eye, and it also made me realize that when you use your imagination, anything can happen.”

Success is based on following guiding principles, somewhat like the importance of good directions on a road trip. If we veer off course, things get bumpy, although we may see some interesting sights. For some people, that’s called adventure. For others, it is needless risk-taking. You have to know our vehicle. In our work with extraordinary people, we discovered six guiding principles that work to enhance their experience.

Standing On The Shoulders

It is a metaphor of dwarfs standing on the shoulders of giants (Latin: Nanos gigantum humeris insidentes) and expresses the meaning of “discovering truth by building on previous discoveries.” This concept has been traced to the 12th century, attributed to Bernard of Chartres. Its most familiar expression in English is by Isaac Newton in 1675: “If I have seen further, it is by standing on the shoulders of Giants.”

“I was in a stream that turned into a river that became an ocean. All I did was swim.”

— Don Keough, chairman Allen & Co.

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Jeff Cunningham
Jeff Cunningham

Written by Jeff Cunningham

Behind the image: Inside the lives of the world’s most intriguing moguls, disruptors, and oddballs

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