How to get lucky

One mistake at a time

Luck gets a bad rap. Largely because people have the audacity to suggest that it doesn’t exist. Believing in luck is dismissed as a superstition–a symbol that can’t affect the outcome of a situation.

I heartily disagree. Without a healthy dose of luck, there’s no way that I would be in my current position. Probability doesn’t shine kindly on me: I’m an Indian kid who moved from the Middle East to Canada on the cusp of Canadian winter. I knew no one, had little money, and a very, very loose plan. But I’m still here. I’ve started and sold companies, I have a great family, and good friends.

In short, I consider myself a lucky man.

Luck isn’t a divine ingredient. It’s not something that falls from the sky. Rather, luck is a series of self-fulfilling prophecies that you have to be equal parts presumptuous and humble to create. I have always felt like a lucky person, and so I have been very lucky. I can almost hear you rolling your eyes at how irritating that sentence was. But the research has actually uncovered empirical evidence to back that statement up. The formula of presumption and humbleness that I mentioned above works like this: presumption assumes that you will find success; humility assures that you will work to find it.

People hear “luck” and start to feel like their life is a series of flukes. In my experience, those who dismiss the influence of luck are those who can’t give up control. The thing is, our lives are absolutely subject to randomness. We have a tendency to stamp happenings with an explanation to avoid accepting that there may not be one. We are afraid of the unknown.

One story that has always stuck in my mind as a great example of luck, randomness, and saying yes to chance, is Slack’s origin story. The 2.8-billion dollar unicorn was born of a failed project that was threatening to bankrupt Stewart Butterfield and his team. In an effort to make good on the $17 million he’d taken from investors, he threw Slack–then a simple prototype that his game-engineers has used for intra-office communication– at the wall. And did it ever stick.

One of the foremost researchers on the topic of luck (there are actually quite a few) is Richard Wiseman. He suggests that by maximizing your chance opportunities, you’re actually able to create more luck. By definition, chance is “the possibility of something happening.” Truly lucky people become skilled at recognizing and acting upon opportunities for chance, thereby expanding the options available to them. They relax into and seek out unknown circumstances. They widen their networks. They ask just for the hell of it. Someone says yes, and you’ve suddenly got a little luck. The trick now is to leverage it, and to make a little more.

Here’s where the self-perpetuation kicks in: navigating new experiences is a skill you can practice, and improve upon. With such practice, you begin to develop an intuition about which chances are going to be lucky ones. Of course, you can never know for sure. The point of luck isn’t to become a gambler. The point is to learn how to identify and take meaningful risks. And should those risks not pay off, to have built a mindset that says “next time.” A great example of luck well played actually comes in the form of golf, a sport I hate, but nonetheless. In an interview, pro golfer Colin Montgomerie explains how holes-in-one aren’t a product of luck alone. Typically, a “sensible” play ends up with the drive landing slightly below the hole itself (apparently, making a downhill putt is difficult?). So a hole in one is actually a reckless play. Or a mistake.

Failure is a friend of luck: it tests your belief in yourself. I have had close calls in my life and my business. Anyone who runs a company would tell you the same: when you do what you love, failure is personal. In his research, Wiseman has also found that lucky people expect good fortune. Not because they are arrogant or privileged (well, some are), but more related to their having a generally optimistic point of view, and making a point of clearing negativity out of their minds. When you’re confident your future is going to be good, you’re much better able to persist in times of failure. You’re also generally more pleasant to be around, which helps with networking and making friends.

On this same note, when bad luck (life is just a series of random events, after all) DOES happen, people who have this mindset are much more likely to take control of the situation. After all, lucky people know that the world is random, and that by simply participating in an experience they are able to influence it.

I really believe in luck. However I find when I share this philosophy with other people, they often roll their eyes.

“Easy for you to say. You’re already lucky.”

That’s true. I’ve been practicing luck for about 10 years now. And it is a practice.The hard times are going to happen. Rather than waste time dreading them, and worrying yourself into a hole, think about how those glitches will change your perspective. Think back to Butterfield. Sometimes your fuck-ups will actually be a great move. Let debacles inform your luck, not inhibit it. If you can do that, you’re already lucky.