The Serendipity Paradox: Why Luck Isn’t Just for Gamblers
There’s a peculiar irony in how we talk about luck. We either dismiss it as a fluke or romanticize it as some mystical force. But what if luck—or serendipity, as I prefer to call it—is neither? What if it’s the invisible thread weaving through our lives, shaping outcomes in ways we can’t fully control but can, perhaps, better understand?
I’ve spent years dissecting this idea, both in my career and in conversations with some of the most successful people I’ve met. And here’s what I’ve come to realize: serendipity isn’t just about being in the right place at the right time. It’s about recognizing that the right place and the right time often find us, whether we’re ready or not.
The Myth of Meritocracy
One thing that immediately stands out is how uncomfortable we are with the idea that luck plays a significant role in success. We’re raised on the gospel of hard work—the notion that if you grind long enough, success is guaranteed. But here’s the kicker: hard work is necessary, but it’s not sufficient.
Take my own journey, for example. I’ve worked in finance for decades, and while I’ve put in the hours, I can’t ignore the moments where serendipity stepped in. Like the time I called the market bottom in 2009. Was it skill? Partly. But it was also the fact that my wife’s school calendar gave me the space to step back and see the bigger picture. Or the time I met Josh Brown by the pool—a chance encounter that led to a transformative partnership. These moments weren’t planned; they were allowed to happen because I was open to them.
What many people don’t realize is that success is often a collision of preparation and randomness. We like to think it’s all about merit, but the truth is messier. Personally, I think this is why so many successful people downplay luck—it’s easier to believe in a world where effort alone determines outcomes.
The Uncomfortable Truth About Luck
Here’s where it gets interesting: luck isn’t something you can control, but you can position yourself to be lucky. It’s like increasing your surface area for serendipity, as Cate Hall puts it. But even that phrase feels misleading. Are you really increasing luck, or are you just increasing your chances of being in the right place at the right time?
From my perspective, the latter is closer to the truth. Luck isn’t something you manufacture; it’s something you invite by being curious, persistent, and open to opportunities. Take Howard Marks, the chairman of Oaktree Capital. When I interviewed him, he was refreshingly honest about the role of luck in his success. He didn’t dismiss hard work, but he acknowledged that fortune had smiled on him in ways it hadn’t for others.
This raises a deeper question: if luck is such a significant factor, why do we spend so much time obsessing over skill and effort? I think it’s because admitting the role of luck forces us to confront the fragility of success. It’s humbling—and for many, that’s uncomfortable.
The Hidden Patterns of Serendipity
If you take a step back and think about it, serendipity isn’t random in the way we often assume. There are patterns, even if they’re not immediately obvious. For instance, my decision to start tracking housing data in the 2000s wasn’t random; it was driven by my mom’s career as a real estate agent. But the fact that this knowledge positioned me to predict the financial crisis? That was serendipity.
What this really suggests is that luck often emerges from the intersections of our lives—our interests, relationships, and experiences. It’s not about waiting for the stars to align; it’s about creating a life where the stars can align.
A detail that I find especially interesting is how often serendipity is tied to relationships. My wife, for example, came into my life because I asked a girl to dance at my high school prom. That decision, made on a whim, shaped the course of my personal and professional life in ways I couldn’t have predicted.
The Paradox of Preparation
There’s a saying I’ve always found contradictory: “Luck is where preparation meets opportunity.” On the surface, it makes sense. But if you dig deeper, it’s problematic. Preparation is within your control; opportunity often isn’t. So, are we really talking about luck, or are we just repackaging hard work?
In my opinion, this phrase misses the point. Luck isn’t about meeting opportunity; it’s about being available to meet it. That’s why I’ve always emphasized curiosity, networking, and mastery in my career. These aren’t just strategies for success; they’re ways to increase your odds of being in the right place at the right time.
But here’s the paradox: the more you chase luck, the less likely you are to find it. Luck thrives in the spaces where you’re not trying too hard—where you’re open to possibilities without being attached to outcomes.
The Future of Serendipity
As we move further into an era dominated by algorithms and data, I can’t help but wonder: are we engineering serendipity out of our lives? Algorithms are designed to predict and optimize, but serendipity thrives in the unpredictable. What happens when we lose the ability to stumble upon something unexpected?
This raises a deeper question: can we design systems that preserve the element of chance? Or are we doomed to live in a world where everything is calculated, and nothing is left to fate?
Personally, I think the answer lies in finding a balance. We can use data to inform our decisions, but we shouldn’t let it dictate them. Serendipity requires a degree of chaos, and I, for one, hope we never lose that.
Final Thoughts
Serendipity isn’t just a nice word for luck; it’s a reminder that life is messy, unpredictable, and beautifully imperfect. It’s the reason why two people can work equally hard and achieve wildly different outcomes. And it’s the reason why, despite all our planning, the best moments in life are often the ones we didn’t see coming.
So, the next time you find yourself at a crossroads, remember this: hard work is essential, but it’s not the whole story. Sometimes, the most important thing you can do is show up, stay curious, and be open to whatever comes your way. Because in the end, that’s where the real magic happens.
