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Roger Federer’s advice to students also works for investors: You can be wrong almost half the time and still win.ASANKA BRENDON RATNAYAKE/The New York Times News Service

When Roger Federer delivered the commencement address at Dartmouth College last June, the tennis legend offered something more enduring than a motivational pep talk – he gave a masterclass in decision-making.

Mr. Federer shared a stat that surprised many: “In the 1,526 singles matches I played in my career, I won almost 80 per cent of those matches … [but] even top-ranked tennis players win barely more than half of the points they play.” In fact, he won just 54 per cent of points across his career.

What mattered wasn’t perfection – it was focus and resilience. “When you lose every second point, on average,” he told graduates, “you learn not to dwell on every shot.” The goal isn’t to win every point. It’s to play the next one with full commitment.

That mindset – intense focus in the moment, but letting it go after the moment has passed – has surprising relevance in investing.

In 2021, BlackRock portfolio manager Ronald van Loon published research in the Journal of Portfolio Management asking a simple question: How often do professional investors actually need to be right to beat the market?

His answer: not very often. In U.S. equities, outperforming the market required a success rate of just over 53 per cent. For fixed income, it was closer to 51 per cent.

That echoes Mr. Federer’s 54 per cent. You can be wrong almost half the time and still win – if your strategy is sound and you get the cornerstone decisions right.

This isn’t just a technical insight. It’s a psychological reset. Many investors act as if each trade must be a winner, each financial choice perfectly timed. But as Mr. Federer’s point-win ratio shows, individual outcomes matter less than the pattern of decisions over time.

In fact, overconfidence in precision often backfires. Research consistently shows that frequent traders underperform. One study found that the heaviest traders lagged buy-and-hold investors by more than seven percentage points annually. The problem wasn’t intelligence; it was obsessing over daily price movements instead of focusing on long-term wealth-building fundamentals.

The same principle holds in personal finance. Success often comes down to a handful of choices: building an emergency fund, saving consistently, avoiding high-interest debt, and staying invested through market cycles. Get those mostly right, and you’re on track. Obsessing over whether to buy Stock A or Stock B? Much less important.

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There’s also evidence that wealth often hinges on a few foundational life decisions. Married couples build wealth faster – one study showed a 77-per-cent increase in net worth over single people, with gains compounding year over year. Geography matters too: moving from a high-cost to low-cost city while maintaining income can yield enormous long-term savings. Yet people often stress more over optimizing grocery bills than over these life-altering choices.

Mr. Federer’s second big point was about resilience: “The best in the world aren’t the best because they win every point. It’s because they know they’ll lose – again and again – and have learned how to deal with it.”

Investors face the same challenge. Markets fall. Strategies disappoint. Setbacks are part of the process. What matters isn’t avoiding failure – it’s not letting failure define your next move.

The ability to treat each new financial decision as independent from the last is crucial. Too often, past mistakes cloud future judgment. The investor who sold everything during the 2020 crash may still be sitting out the recovery, paralyzed by regret. But, as Mr. Federer said: “When it’s behind you, it’s behind you.”

Research supports this mental flexibility. Studies show that financial literacy, mental budgeting, and self-control have a bigger impact on financial well-being than predictive skill. It’s not about brilliance – it’s about process and discipline.

That’s why planning works. Not because it ensures perfect execution, but because it gives you structure to respond when things go off course. According to a study by Charles Schwab, 96 per cent of people with a written financial plan say they feel confident about reaching their goals, and 76 per cent say they feel more in control of their money.

So how many financial decisions do you need to get right?

Mr. van Loon’s research – and Mr. Federer’s career – suggest it’s fewer than you might think: just slightly more than half.

Focus on the 54 per cent that truly matters: save consistently, avoid high-interest debt, invest for the long haul, and protect yourself against major risks. Success doesn’t require perfection. It requires focus, resilience, and the humility to let go of what you can’t control.

Mr. Federer didn’t win every point. But he won when it counted. The same is true for investors who focus on getting the big calls right and letting go of the rest.

Michael Jordan once said: “I’ve missed more than 9,000 shots in my career … I’ve failed over and over and over again. And that is why I succeed.” Like Mr. Federer losing 46 per cent of his points, greatness emerges not from avoiding failure, but from responding well when it comes your way.

Sam Sivarajan is a keynote speaker, independent wealth management consultant and author of three books on investing and decision-making. His forthcoming book will explore how to thrive in a world of uncertainty.

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