The term serendipity was coined on January 28, 1754 by Horace Walpole, the fourth Earl of Oxford, who stole those first three syllables from the Persian folktale The Three Princes of Serendip. That story is about three banished princes who wander outside their kingdom in despair until a series of happy coincidences leads them back to the throne (or some strange timeshare co-throning arrangement). As Walpole originally wrote, those blessed with serendipity are “…always making discoveries, by accidents and sagacity, of things they were not in quest of.” Nowadays, we call those people “lucky sons of bitches.” Times change.
Luck is, as they say, a fickle woman, undirected and unreliable. Relying on luck as a regular buoying force is a fool’s game (remember Marlon Brando in “Guys and Dolls”) like playing scratch cards or bocce. You can’t create it and you can’t destroy it, but that doesn’t mean you can’t create the conditions in which luck thrives. This is called “sagacity,” a term you don’t hear much nowadays and an idea that warrants consideration, especially in the age of optimization. Here is a beginner's guide to cultivating serendipity.
Clear the path: You want a promotion. So, take control of everything you can. The baseline is good, hard work, timeliness, and courtesy: if another employee has something to say against you, it should be nothing more than a difference in a professional strategy.
Make social space: There’s no particular virtue in being the guy no one has anything bad to say about. You want to be the guy that people actively recommend. In order to be that guy, you have to seem like a multi-dimensional human being. The best way to do this is to engage with your co-worker while not actually working. If you smoke, make the most out of corner smoke-breaks. If you’re a caffeine-hound, spearhead a trip to get coffee. When you create “extracurricular” time at work, time to joke, ask about families, and tell your own stories, you’re not only creating a happier work environment, you’re positioning yourself as someone who co-workers want to recommend when something big comes down the pike.
Embrace flexibility: Writers are coached to “kill their darlings”—delete the cute shit - for the good of the larger piece. The same principle can be applied to professional choices. Sometimes, getting attached to bits and moments of your working life inhibits decision-making. A nice commute, a fun relationship with a co-worker, or the burden of sunk costs are not reasons for professional complacency. Always be attentive to opportunities, large or small, that, though they hold immediate logistical or interpersonal challenges, will position you more favorably five years down the line.
Be Honest (With Yourself): Be brutal: Is your career panning out? If not, if things are just good enough to lull you into stasis, move on, ASAP. There is no worse place than to plant the seeds of luck than in the fallow ground of “fine."
Take Initiative(s): As Gretzky posters across North America counsel, “You miss 100% of the shots you don’t take.” If that metaphor works for you, go with it. We prefer to think of it this way: If you’re not doing anything, you’re not doing anything. In small terms, embracing risk can mean pitching ideas to senior managers or taking a chance on a big but unstable client; in grand terms, that means identifying what skills, experience, and network you have, and starting a business that makes use of these assets.
Be generous with your time: While we’ll hold back from invoking “karma,” doing right by others is more than an ethical imperative—it opens an avenue for you to be the recipient of favor. Cover for co-workers when they need it, help friends lug boxes from apartment to apartment, babysit your sister’s kids, and don’t just write a check to an African NGO—volunteer locally. People want to help those who have helped them: Don’t stop them.
Photos by Warner Bros.