On Luck & Serendipity

I don’t throw salt over my shoulder, and I am by no means particularly superstitious or religious. But I’ve had a peculiar affair with the number 18 for much of my life, and figured I’d share some thoughts on why we look for signs of luck and how they help us.

18
The number 18 seems to always pop up for me at inflection points in my life. As an undergrad at Cornell, I was assigned “skb18” as an email address, as the 18th person with the initial SKB at the university. My phone number at my first job was 902–1800 (9x2 also wasn’t lost on me). I was accepted to business school on January 18th. My wife’s birthday is 9/9/81 (which can be twisted to ring all kinds of bells on my 18 radar). The first investment I ever made in the founding of Behance was $18,000 to cover a 5 month contract for the designer who became my co-founder. The first home I purchased with my wife was on the 29th floor of a building in NYC (again, some math required, but it’s there). And the list goes on.

Why do we look for inconsequential patterns and signs? What do they mean? And what does our observance of such quirks teach us about the role of luck and serendipity in life?

Here’s one way to think about it: The only control we have over life is when we’re able to make decisions. Otherwise, life just happens to us. As a result, decisions are precious and difficult, especially when we lack sufficient data and experience. Where you go to school, who you marry, what job you choose, what risks you’re wiling to take in your career…you make these decisions only with a “leap of faith.” And this massive leap leaves you with a gap of uncertainty.

The big question is, how do you fill the gap so you can live your life (or execute your big idea) without “knowing” whether or not you made the right decision?

How can you achieve conviction without certainty?

Pattern recognition helps. If you’ve had a lot of experience in the area, you can bridge the gap with gut instincts that are informed from your past. But often times, these pivotal life decisions happen early in life and you need some other force to bolster your confidence.

Enter serendipity — “the occurrence and development of events by chance in a happy or beneficial way” — the things we notice and grasp on to as handrails along the tight rope of the unknown. The random run-in that makes new terrain feel familiar, the coincidence that calms our nerves, or the “sign” that catches your eye. What if luck and serendipity are always there but only harvested when we need to tip the scale of conviction?

I’ve always believed that luck is not a thing, it is a perspective. It is a lens through which you see an occurrence — often a common one — as an opportunity (or at least a signal that emboldens you). You see luck if and how you want, and when you see it and choose to capitalize on it, you benefit from it. If you have bold plans, you need it.

Perhaps I’ve taken note of the number 18 throughout my life as a way to venture forward with no headlights? Perhaps “18” — and as many derivations of it as I need — is just the manifestation of confidence without reason? It’s probably always there, along with every other number, but I pluck it out to supplement the other more rational drivers of my conviction.

The role of luck and serendipity also grounds us. When we admit that some part of our good fortune can only be attributed to luck, we remind ourselves that nothing profound is accomplished alone. The role of others — and other circumstances beyond our control — play a critical role. When big decisions are made and risks are taken that require a leap of faith, we tap into the inexplicable. If it helps you endure the leap, then by all means find your magic number.