Originally, I thought about naming this post “Getting Rich by Getting Lucky Doesn’t Feel So Good.” But as time passed, I realized that sometimes, getting lucky actually feels better as you reflect on it more. This shift in perspective can have significant socioeconomic consequences, such as the tendency to accumulate wealth and increase inequality. Luck can also lead us into delusional thinking, setting us up for future disappointments.
On May 10, 2024, I experienced a stroke of luck—not financially, but in a USTA tennis league match. My doubles partner and I initially lost the first set 1-6, struggling to return powerful serves from our opponents. It seemed only a miracle could save the match for us.
Then, the unexpected happened in the second set. During a crucial point, one of our opponents began to limp after hearing a “pop” in his calf. Despite the injury, he chose to continue playing rather than forfeit. We eventually won 6-2 in the second set and 10-3 in the tiebreaker. While we had started playing better, winning seemed unlikely if he hadn’t been injured.
This incident left me mixed emotions. Over my years playing more than 100 USTA matches since 2009, I’ve never wanted to win by default. Initially, I felt guilty for winning due to my opponent’s misfortune. However, as time passed, I began rationalizing the win, convincing myself of my deservingness based on various reasons, such as my previous unbeaten streak and the effort I put into preparing for the match.
This experience parallels getting hired based on identity or legacy—benefits that often come with internal conflicts about worthiness and performance anxiety. In smaller organizations where you cannot hide, this pressure is magnified, sometimes leading to feelings of fraudulence or failure.
Competing in sports is mercifully straightforward. It’s about preparation and performance, not identity or connections, which is why the push for diversity isn’t as pronounced in sports as in other areas. This meritocracy is stark compared to the business world, where about 90% of startups fail, despite being filled with top talent. If you doubt your abilities, steering clear of startups or entrepreneurship might be wise, as the exposure and risk of failure are high.
During the pandemic, I discussed the book industry with an author who landed a $400,000 deal despite expectations setting her advance around $50,000. The book flopped, selling far below expectations, but she had already secured her “eight book deals’ worth” of payment. This story illustrates a key point: if you find yourself on the favorable side of luck, seize the opportunity—because if you don’t, someone else will.
The tennis match where I won against an injured opponent felt especially poignant because the injured player had previously rejected me from joining his team. This victory, though hollow, felt like a small personal redemption.
But luck in competition, as in life, should not be a constant reliance. As I age and my physical capabilities wane, I appreciate the occasional lucky break more, yet I never want it to define more than 10% of my successes. True satisfaction comes from winning—or succeeding—on one’s own merits.
Life will never be completely fair. Those with great advantages often also find themselves lucky. It’s essential to acknowledge the role of fortune in our successes and strive to share our good fortune when possible, like MacKenzie Scott does with her philanthropy.
In summary, we all encounter luck throughout our lives. What matters is how we handle it—by acknowledging its role, leveraging it responsibly, and continuing to strive for personal and professional excellence regardless of the circumstances.
