Roger Federer on Perspective: The Only Game Worth Winning

It was hard for anyone who heard Roger Federer’s commencement speech at Dartmouth College not to be inspired by the wisdom of a 20-time Grand Slam winner. The key points–Effortless is a myth; It’s only a point; Life is bigger than the court –are especially relevant for anyone leading a team.

Still, while the message will resonate with leaders, how many could realistically follow such well-grounded advice in their early work life, or even mid-career? Probably not many. It’s easier to give this kind of advice after a successful career rather than during a rollercoaster climb.

Why? The pressure to succeed is usually so high and reputation is at stake with financial stability usually top-of-mind. It’s unlikely ambitious leaders could give the same level of battle-honed counsel, as too often, perspective gets lost as three factors dominate their mindset: goal obsession, ego domination, and work-life imbalance. 

While individually troublesome, together they’re toxic.

1.   Goals Dominate Mindsets.  

Most A-type personalities think primarily about medals and money, driven by a tribal instinct to win. Few can tolerate the pain of losing. 

At Stanford’s first commencement address by an athlete, tennis legend John McEnroe emphasized the danger of that all-consuming  win/lose mentality: “Measure your success by how much you evolve, not necessarily how much you win.”  

Of course, aggressive battles are played out in every industry. Nowadays, the AI crown is heavily contested by data behemoths. Time will tell who wins. In the meantime, goal-hunting leaders risk missing opportunities derailed by a range of power, ego, risk, and identity-based misjudgment traps, as illustrated in my book Tune In.

Great leaders and entrepreneurs know how to handle repeated setbacks. Like athletes, writers, actors, and job applicants are frequently rejected. Federer tells how he only won 54 percent of the points over 1,526 matches, even though he won 80 percent of his matches. That’s almost a coin toss for each point. The disappointment is no different from facing sales underperformance or client defections. 

The trick is expectation management about success, notoriety, and awards. Hollywood’s Ryan Reynolds learned this early: “Expectations were eating me alive.” When you’re up, the only place to go is down, even if that’s hard to accept. 

2. Ego Dictates Decisions. 

In my experience, many business leaders don’t move on from disappointment or loss quite so easily. Ego typically gets in the way. While the business mind is consumed with reputation preservation and optics, athletes move on a lot more quickly, absorbed by the momentum of the game. 

Federer rightly states “When you’re playing a point, it has to be the most important thing in the world, and it is. But when it’s behind you, it’s behind you.” 

Novak Djokovic made a similar comment when he won Roland-Garros last year.  He advised us to “Live in the present, forget the past, as the future will just happen.” He places psychological distance between the error and the next move, as the winner’s mind is anticipating the next opportunity. Michael Jordan agrees: “I have failed over and over again, and that’s why I succeed.”

When most of us make a mistake or even tell a bad joke, we can irrationally replay the moment. We’re convinced everyone is watching and suffer humiliation on repeat. It’s known as the spotlight effect. But the reality is, others are too busy focusing on themselves–except when they have a vested interest or something at stake. In sports, fans and competitors scrutinize every game move, and in business, it’s customers, employees, competitors, regulators, and shareholders.

3. Balance Dissipates Perspective.  

For a leader, growing your business can become an all-consuming ecosystem with like-minded people. You live with your competition, constantly tuned in. At his final pro match, Federer was seated on the bench next to his biggest rival, Rafael Nadal. Both sobbed. With legacies intertwined in mutual respect, maybe in that moment, they gained valuable perspective. “Life is bigger than the court,” after all.

When founders struggle to let go of their organizations, some stay on in executive chairman roles. Founders Michael Bloomberg, Warren Buffet, and Richard Branson still play strong roles in their organizations. 

Similarly, athletes remain within the sport as spectators or commentators. Sir Alex Ferguson still attends Manchester United matches, even though he retired as a manager in 2013. 

When 39-year-old Serena Williams retired in 2022 as one of the highest-paid female athletes, she rightly spoke about the need for a well-considered retirement plan. 

Looking Ahead.

Like the entrepreneur, in tennis the court and adoring fans become part of your DNA, fused with personal identity. Like any competitor, by controlling your mental frame, you broaden your perspective beyond winning or being the best in your field, and improve your ability to cope with potential disappointment.

Life goes on. Time passes, and with it, our obsession with winning, pseudo-priorities, and transient obsessions. No doubt Rafa Nadal and Andy Murray will take note of Federer’s inspiring address as they face a retirement decision this summer. 

When the best sports leaders of this generation impart their wisdom, it’s time for us to tune in.