What Roger Federer’s Career Can Tell Us about Success, Failure, and Career Satisfaction

At the ripe age of 41, Roger Federer announced today he is retiring from the world of professional tennis. After 1500 matches and 103 title wins including 20 in grand slam events, Federer announced he would be leaving the sport following the Laver Cup next week in London. While his “greatest of all time” (GOAT) status is disputed, he’s clearly one of the GOATs of tennis. It’s worth reflecting on how that kind of greatness gets built.

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In his 2021 book, Range: Why Generalists Triumph in a Specialized World, author David Epstein recounts Federer’s background as an example of the importance of wide-ranging development in building expertise. Federer’s mother, a tennis coach, famously refused to play tennis with her son as he was growing up because his style of play was so unorthodox that it was nothing but frustration to play against him. Instead, she encouraged him to try a wide variety of athletics:

He would kick the ball around with her when he learned to walk. As a boy, he played squash with his father on Sundays. He dabbled in skiing, wrestling, swimming and skateboarding. He played basketball, handball, tennis, table tennis, badminton over his neighbor’s fence and soccer. He would later give credit to the wide range of sports he played for helping him develop his athleticism and hand-eye coordination.

In a society and culture that is hyper-focused on developing narrow expertise, Federer’s route to the top started with “play” across a wide spectrum of activities that developed different skills. All these different skills came together when Federer decided in his teens that tennis would be his vocation.

Epstein argues (and I agree with him!) that the future belongs to generalists, people who can integrate knowledge and skill across a variety of domains. It fosters a mindset of curiosity and experimentation in work, allowing individuals to try out different paths. By trial and error (and success) we are able to identify the type of work that is personally satisfying and sustainable. This broad-based approach is an insurance policy for one’s career, allowing workers to move between jobs and sectors with a portfolio of knowledge and skills anchored by the master skill of flexibility.

One survey done a few years ago found that 93 percent of parents would like their child to be an engineer. As the new school year begins, it’s a good time for a gut check: Are we giving our kids enough “range” to consider the almost unlimited opportunity the American economy affords, or are we so worried about their economic futures we are “funneling” them toward the kinds of jobs we think are “secure,” and thereby ignoring natural interests and abilities?  In my view, taking on a course of study, job training, or career you don’t really like because it is advertised as a good economic payoff may end up being the riskiest play of all, and a shortcut to burnout and professional disillusionment.

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