The Pursuit of Outliers
“Understand power laws. Outlier math rules all.”
Life often feels like a lottery where most tickets yield nothing, and a few yield jackpots. This is not an illusion; it’s a reflection of reality’s heavy-tailed nature. Most of the value in the world—whether in wealth, ideas, relationships, or opportunities—comes from outliers. But because outliers are rare and counterintuitive, most people fail to find or even recognize them. Worse, they often sabotage their search with bad strategies, optimizing for the average instead of seeking the exceptional. The trick to winning this game is to embrace its fundamental unfairness: the world rewards persistence, boldness, and the willingness to fail repeatedly in pursuit of the improbable.
Heavy-tailed distributions are everywhere. Incomes, for example, are not evenly spread. The median person lives on far less than what even the bottom of the top 1% earns. Startups are another classic example: a handful of companies like Airbnb or Stripe define the entire value of a portfolio, while the rest barely survive. And it’s not just about money. The impact of ideas, the joy of relationships, and even the outcomes of personal projects follow the same skewed pattern. Most things are mediocre, but a few are transformative.
This unevenness is frustrating because it feels unnatural. We expect life to be like picking apples, where any random one will do if it isn’t bruised. But life is more like panning for gold: hours of sifting dirt for the occasional glittering flake. The problem is most people don’t realize they’re panning for gold, so they give up too soon or accept rocks as “good enough.” They don’t take enough samples, and they don’t filter for the right qualities. They aim for competence when they should aim for brilliance.
The way to beat heavy-tailed distributions is to sample relentlessly. If you’re blogging, write post after post, knowing that most will flop, but one might go viral. If you’re dating, meet as many people as you can, even if most first dates go nowhere. The secret to finding outliers is simple: see more of the world. This is the opposite of how most people behave. They get discouraged after a handful of failures, mistaking bad luck for bad strategy. But failure is inevitable when you’re searching for something rare. Each failure is not evidence that you should stop; it’s proof that you’re still in the game.
Finding outliers also requires changing how you evaluate opportunities. Most people optimize for what’s “good enough.” They make checklists, ticking off easy-to-measure qualities like job titles, income, or physical attractiveness. But outliers often look bad at first glance. Airbnb sounded like a terrible idea: strangers sleeping in your home? Yet it worked because its founders had the grit and adaptability to turn skepticism into success. The real art lies in filtering for hidden potential, not superficial perfection. Don’t ask, “Is this good?” Ask, “Could this be amazing?”
Outliers also demand persistence. Success in a heavy-tailed world often requires long-term investment. This is why some people settle: they underestimate how good the best outcomes can be. If your current job or relationship feels “pretty good,” you might assume it’s the best you’ll find. But what if you’re only at the 90th percentile? Rejecting something good is hard because it feels like risking everything. But the truth is, abundance is real. If you found one good thing, you can probably find another. Settling is only rational when you’re confident you’ve hit the extreme upper tail, and most people don’t even get close.
The pursuit of outliers is demoralizing because it involves a lot of failure. This is why most people give up. They mistake the inevitable grind for a sign that they’re on the wrong path. But the grind is the path. The process of sampling and filtering, of trying and failing, is what leads to success. You don’t need to be smarter than everyone else; you just need to be stubborn enough to keep going when others stop. Heavy-tailed distributions reward endurance.
The world doesn’t hand you outliers; it hides them in plain sight, among the clutter of mediocrity and failure. To find them, you have to train yourself to think differently. Take more chances. Fail more often. Ignore the conventional wisdom that says a few samples are enough. Remember that the best outcomes look unimpressive at first. And above all, trust that the process works. Outliers are real, and they’re worth the effort. You just have to keep searching.
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My aim is to live a balanced and meaningful life, where all areas of my life are in harmony. By living this way, I can be the best version of myself and make a positive difference in the world. About me →