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How to Put Planned Serendipity to Work For You and Your Business

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Controlled Sloppiness

Scientists have noted for many years that there are clear benefits to avoiding overly controlled research situations. Many have noted how Sir Alexander Fleming stumbled on penicillin discovery in part due to the untidiness of his own lab. Similarly, Professor Salvador Luria of the University of Illinois described in 1952 how “controlled sloppiness” permits the occurrence of fruitful accidents as a general rule:

Our story has as its critical episode one of those coincidences that show how discovery often depends on chance, or rather on what has been called “serendipity”—the chance observation falling on a receptive eye. The episode is a good illustration of the principle of “controlled sloppiness,” which states that it often pays to do somewhat untidy experiments, provide one is aware of the element of untidiness. In this way unexpected results, sometimes real discoveries, have a chance to come up. When they do, we can trace their cause to the untidy, but known, features of the experiment.

Salvador Luria, “The T2 Mystery”, Scientific American 192 (April 1955): 22, 93-94. 

Scientific discoveries…are often quite unpredictable. Planned and organized research, directed to a given end, is often highly successful, but frequently some strange maverick of fact may present itself, some curious exception to what was confidently predicted, that may be far more significant than everything else…Serendipity, the happy faculty of finding things that one did not set out to seek, is an important trait of every scientist.

Edmund W. Sinnott, biologist and former dean of the Graduate School of Yale, Think (November 1951)

I just caught this riveting documentary on Bill Cunningham, the legendary fashion photographer for the NYTimes (as well as many other publications over the years). To him, the best runway show is on the streets, where everyday people wear the clothes the way they like them, as the most personal of self-expressions. Bill has the quintessential geek brain—obsessive curious, able to catch what others miss in a flash, and strangely resistant to conventional wisdom despite over sixty years doing his craft. It’s these qualities that make him prepared for the serendipitous photo opportunities and trend-spotting that he never lacks for. He can’t walk down the street without getting lucky in this way, and it’s given him one of the longest running (and most resilient) careers in a media world that continues to change at blinding speed.

Synchronicity versus Serendipity: Ideas Not to be Confused

Last week Lane and I had the good fortune to attend the Summit Series, which above else, must be described as a large-scale exercise in planned serendipity. This year the TED-like conference was held in Tahoe, at the scenic Squaw Valley, not quite as remote as the Caribbean cruise ship of last year, but just far enough removed from real life to nudge participants into a more open state of mind.

The conference’s success is based on an incredibly well-curated guest list of ~600 over-achievers from a wide range of backgrounds and careers. It extended to the design of gathering spaces that encouraged movement and surprise (including my favorite, a secret speakeasy behind a broom closet). And it culminated in a schedule that was so full of amazing talks and activities that it became too rich and fast-moving to plan around. After a few hours it seems impossible to NOT get derailed by a chance meeting while walking from one event to another. Confronted by this dynamic eventually most people tend to relinquish their personal schedule to chance, even when they have some ideal schedule in mind. At the Summit Series, many of my most memorable moments were conversations with people I’d never know to seek out—a psychoanalyst/author who focuses on women facing forty, a designer of hand-made ties from a post-apocalyptic Detroit, the host of a popular show on MTV

This surprise is all by design. In the opening ceremony one of the organizers announced to all the attendees a few “unwritten rules” for the event, which included “build friendships,” “show love,” “have fun,” and two others that struck me as particularly relevant to planned serendipity:

Go on a learning safari:Everyone has something to teach. Everyone has something to learn. Take an intellectual, spiritual and creative journey.”

Embrace Synchronicity.The unexpected moments are often the most meaningful. Embrace them.”

What great advice, I thought. Who could argue with these rules? Yet something was rubbing me the wrong way. Hmmm. “Embrace synchronicity.” Synchronicity??? “Unexpected moments are the most meaningful?” That’s not synchronicity at all, I wanted to blurt out. That’s serendipity. The words may sound the same, but they have VERY different meanings. Blurring the lines of these ideas obscures how equally interesting and useful each one is.

Serendipity means looking for one thing and finding another. It’s a regular occurrence for anyone with an inquisitive mind, and a bedrock of scientific, artistic and business breakthrough. It was coined by a British aristocrat to impress his pen pal way back in the 1700s.

By contrast, synchronicity is a far more recent invention—it was coined in the 1920s by Carl Jung to mean something quite distinct. The mystically inclined psychoanalyst Jung noticed that sometimes two or more events would happen at the same time, without any common cause, but whose coincidence, the mused, might imply a deeper meaning. Perhaps, he thought, we can categorize phenomena by meaning just as credibly as we categorize them by causality. For instance, at the very moment you’re planning a barbecue cookout the Doors song “Light my Fire” comes on the radio. Or you’re thinking that you should call your mom, and at that very moment your phone rings and it’s her! What are the odds? Synchronicity suggests that these parallel events are somehow connected, despite the fact that they’re disconnected.

Jung intended synchronicity to have spiritual connotations, suggesting a larger framework or deeper order behind the logical, one-thing-leads-to-another world we are conscious of. Consider the Police song Syncronicity, on the album of the same name:

A sleep trance, a dream dance
A shaped romance
Synchronicity

A connecting principle
Linked to the invisible
Almost imperceptible
Something inexpressible
Science insusceptible
Logic so inflexible
Causally connectable
Yet nothing is invincible

If we share this nightmare
Then we can dream
Spiritus mund
i

Serendipity, on the other hand, was intended by Horace Walpole to describe a very human “faculty.” It is a skill, not a metaphysical construct, and one entirely susceptible to scientific inquiry and exposition.

So these are two very different concepts, but they do share a very important trait: they rely on the mind to make a connection between two or more things (at least in the observing). The same mind capable of combining the chance discovery with previous experiences or stored ideas may also be likely to notice synchronicity if it occurs. Unlike synchronicity, a single instance of serendipity can take years to fully occur, with the initial observation taking root in the observer’s mind, and only much later becoming associated with something else that transforms it into a true creative leap. On the flip side, synchronicity can sometimes act as a kind of compressed serendipity—one chance event made meaningful by a related event happening at exactly the same time.

As Sting implies in his lyrics, Jung linked the metaphysical dimension of synchronicity to the dream world, both which he also thought exposed a deeper order. While serendipity makes no such claims, the fact is that dreams are an underappreciated path for making connections that matter in our waking life. There are many examples: Elias Howe inventing the sewing machine after dreaming of tribal natives who had holes in the top of their spears (solving the threaded needle that had stumped him), Albert Einstein’s dreams about the nature of time that led to his relativity theory, Friedrich Kekulé discovering the structure of the Benzene molecule after dreaming of a snake eating its own tail. The greatest minds have been those who have connected to their own subconscious as the greatest pattern matching machine at their disposal. 

Serendipity and synchronicity may be very different concepts, but they play well together.