The Paradox of Investing: Why Doing Less Often Means Winning More

Picture this: NASA engineers, perhaps inspired by countless hours spent playing vintage arcade games, recently executed one of the most audacious experiments in space history. They deliberately crashed a spacecraft called DART into an asteroid, aiming to alter its trajectory through the cosmos.¹ The mission wasn't about destruction—it was about understanding how small, calculated actions can create meaningful change. The results wouldn't be immediate; scientists would need months of careful observation to confirm whether their intervention succeeded.

This patient, methodical approach offers a striking parallel to successful investing: sometimes the most powerful moves are the ones that require restraint, precision, and the wisdom to let time do the heavy lifting.

Tennis embodies athletic grace in its purest form. Watch Roger Federer's forehand slice through the air with seemingly effortless precision, or witness Rafael Nadal mount yet another impossible comeback, and you understand why millions are captivated by the sport. While my passion has always resided with soccer—a year-round commitment that left little room for other athletic pursuits—I've developed a deep appreciation for the strategic lessons tennis offers, particularly when it comes to understanding competition at different skill levels.

Here's where it gets interesting: experienced tennis players often share stories about encountering a particular type of opponent that drives them absolutely mad—the so-called "pusher." This player doesn't attempt spectacular serves that kiss the line or execute impossible angles that leave spectators gasping. Instead, they employ a maddeningly simple strategy: keep the ball in play, maintain steady consistency, and wait patiently for their opponent to self-destruct.

The pusher never tries to be a hero. They're content to send the ball back methodically, rally after rally, forcing you to either match their patience or attempt increasingly ambitious shots. Inevitably, frustration builds. You try that aggressive cross-court winner, that blistering serve. The ball catches the net or sails just beyond the baseline. Point lost. Game lost. Match lost.

What makes this so frustrating is that by virtually every measurable standard—speed, power, athletic ability—you might be the superior player. Yet somehow, this seemingly boring, defensive approach consistently produces victories. How is this possible?

The answer lies in a profound insight from Charles Ellis, who built upon the work of Simon Ramo's analysis in Extraordinary Tennis for the Ordinary Tennis Player.² Ramo discovered something that fundamentally changed how we should think about competition:

In professional tennis, approximately 80% of points are won through exceptional execution—brilliant serves, perfectly placed volleys, and aggressive winning shots.

In amateur tennis, approximately 80% of points are lost through unforced errors—serves into the net, missed returns, balls hit out of bounds.

This distinction is critical: professionals are playing what Ramo called a "winner's game," where success comes from superior execution and offensive brilliance. Amateurs, however, are playing a "loser's game," where victory goes to whoever makes fewer mistakes.

The implications are profound. If you're an amateur tennis player trying to win by emulating professional tactics—attempting aggressive serves, going for sharp angles, taking risks—you're employing the wrong strategy. You're trying to win a winner's game when you're actually playing a loser's game. The optimal amateur strategy is counterintuitively simple: play conservatively, keep the ball in play, minimize unforced errors, and allow your opponent to beat themselves.

That's precisely what the "pusher" understands and exploits so effectively.

Now, here's the crucial connection that most investors miss entirely: investing is fundamentally a loser's game that millions of people mistakenly approach as if it were a winner's game.

Just as amateur tennis players lose by trying to play like professionals, amateur investors lose by attempting to trade and time markets like institutional pros. They watch financial media showcasing hedge fund managers executing complex strategies. They read about traders making fortunes through aggressive stock picking and market timing. They see the spectacle of Wall Street and assume that's the game they should be playing.

But here's the uncomfortable truth: for most individual investors, these active approaches don't lead to winning—they lead to self-inflicted losses through excessive trading costs, poorly timed market entries and exits, emotional decision-making, and unforced errors.

Research consistently demonstrates this reality. Studies have shown that the average investor significantly underperforms simple market benchmarks, not because markets beat them, but because they beat themselves through their own actions.³ Just like the amateur tennis player who loses by attempting shots beyond their skill level, investors lose by attempting strategies beyond their capability and understanding.

So what's the winning approach for the amateur investor? The same strategy that works for the amateur tennis player:

Keep it simple. Focus on avoiding mistakes. Play conservatively. Let time work in your favor.

This means:

The pusher wins not through brilliance but through consistency and patience. The successful long-term investor wins the same way.

There's a memorable conversation between David Letterman and Jerry Seinfeld that captures another crucial truth about investing. In 1990, when Seinfeld's show was just beginning, he mentioned a frustration to Letterman: NBC had assigned comedy writing teams to help with the show, but their contributions weren't particularly impressive.

Letterman responded with a penetrating question: "Wouldn't it be odd if they were good? What do you mean they should be giving you great material every day? It's supposed to be hard."

Seinfeld laughed in recognition. Of course it's supposed to be hard. Even the most talented comedians can't consistently produce brilliant material on demand.

This truth governs investing as much as it governs comedy. Finding undervalued stocks, timing market movements, identifying the next great company before everyone else—these things are supposed to be extraordinarily difficult. If they were easy, everyone would do them successfully, and the opportunities would disappear instantly.

The financial media and investment industry, however, profit from convincing you otherwise. They showcase the rare success stories while conveniently ignoring the vastly more common failures. They present investing as a winner's game where skill and effort naturally lead to market-beating returns. This narrative serves their interests—it keeps you trading, subscribing, and seeking the latest "hot" investment strategy.

But recognize this for what it is: an amateur tennis player being encouraged to abandon the conservative game that would lead to victory, and instead attempt the spectacular shots that look impressive but most often result in losses.

Remember NASA's asteroid mission? The spacecraft's collision was dramatic—a high-speed impact captured by cameras from millions of miles away. But the real work came afterward: months of patient observation, careful measurement, and detailed analysis to determine whether the mission achieved its objective.

Successful investing requires the same patient, methodical approach. The excitement isn't in the daily trading, the hot stock tips, or the attempts to outsmart the market. The real success comes from:

This approach may not feel exciting. You won't have dramatic stories about the amazing stock pick that tripled in a month. You'll be the pusher—steady, patient, even boring by some standards.

But when you check your investment portfolio in 10, 20, or 30 years, you'll likely find that this "boring" approach has defeated the vast majority of investors who tried to play the winner's game. You won't have won through brilliance or spectacular execution. You'll have won by recognizing which game you were actually playing and adopting the appropriate strategy.

You'll have won by understanding that in a loser's game, victory comes not from doing everything brilliantly, but from consistently avoiding mistakes.

And that, ultimately, is the most valuable investment lesson of all.