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  • Writer's pictureMac Ling

Serendipity & Self-Discovery

Updated: Jul 23, 2021

Can cultivating opportunities for "accidents" help us reach our goals in ways that deliberate plans cannot?

"The most exciting phrase to hear in science, the one that heralds new discoveries, is not 'Eureka!' but, 'That's funny ..."

- Isaac Asimov

The Three Princes of Serendip

The movie Serendipity (2001) is somewhat inaptly named, at least if we take the word at its technical value. This movie follows a classic romantic comedy trope: Two individuals headed down a seemingly inevitable path ignited by love at first sight decide to inject a bit of "destiny" into their story, and thus the claim is made that if they find each other after this first fateful night, through a series of accidents, that it is meant to be. But here is the salient distinction: Even after they part, they know exactly what they want and exactly what they are looking for. The surprise was that the path became circuitous, but the unexpected discovery aspect that is so important to serendipity—at least as we conceive of it now, as something different from coincidence or fate—is lost. The characters delight less in an instance of serendipity than in one of inevitability; the fact that the meeting happened once suggests that it IS likely to happen again if similar correlations align—it becomes, in fact, less surprising. (Except in the precise opposite case, of course, when a force actively keeps two people apart and is unlikely to change—yet another storied romance trope, after all!). The fact is, as we grow and learn what we like, we tend to make choices that drive certain life possibilities towards inevitability and others towards impossibility. But what would it look like if we purposefully interfered with this tendency?

"Surfing the internet," as we once called it, is a phrase that reflects some of the early hopes of those who constructed the network. They hoped the words would conjure “something that would evoke a sense of randomness, chaos, and even danger” (Polly 1992); in other words, that one would enter into it anonymously and would bounce around a system that would take away some of the barriers of brick and mortar life, and, instead, create the possibility of coming across information that might be wholly unfamiliar and utterly fascinating to the user. The hope (at least one of them) was that we would find things that we did not seek—that we were not on our way to anything, but simply in a state of alertness to the information presented in the moment.

These days, of course, the internet is quite a different place—arguably even more than in real life, it serves up to us what it believes we might most like based on what we in the past have liked; in an attempt at efficiency and convenience, it limits the opportunity for the type of discovery that occurs through unlikely circumstance. This tendency has given rise to ambivalent feelings in the industry, which now boasts a formal inquiry into serendipity in the digital atmosphere—a search for algorithmic systems that would re-insert the fruitful joy of these unfamiliar accidents into an otherwise curated mix.

It was Sir Horace Walpole who purportedly coined the word serendipity, the first instance of which comes to us through a letter that he wrote on January 28, 1754:

“This discovery, indeed, is almost of that kind which I call Serendipity, a very expressive word, which, as I have nothing better to tell you, I shall endeavour to explain to you: you will understand it better by the derivation than by the definition. I once read a silly fairy tale, called ‘The Three Princes of Serendip’; as their Highnesses traveled, they were always making discoveries, by accidents and sagacity, of things which they were not in quest of."

It is interesting that Walpole characterizes “serendipity” as not only a “happy accident,” as we tend to think of the word now, but as something containing a component of what he termed “sagacity.” In this newsletter, we will explore how we can apply our wisdom—about ourselves, about the world—in order to not only let accidents blindly happen and accept them when they do, but to cultivate habits that actively invite them.


YOUR TASK FOR THIS MONTH (...should you choose to accept it)

"You might think of serendipity as passive luck that just happens to you, when actually it’s an active process of spotting and connecting the dots. It is about seeing bridges where others see gaps, and then taking initiative and action(s) to create smart luck. Serendipity is a guiding force in great scientific discoveries but it’s also present in our everyday lives, in the smallest of moments as well as the greatest life-changing events. It’s how we often ‘unexpectedly’ find love, a co-founder, a new job, or a business partner – and it’s how inventions such as Post-it Notes, X-rays, penicillin, microwaves and many other innovations came about."



Instead of walking your regular route home from work, walk another one—precisely the one, perhaps, that none of your instincts tell you is the natural choice for you (because if it is unfamiliar but still accords with your tendencies, the serendipity is thus lessened); you should, of course, do this within reason and safety! “The finest thing about New York City, I think, is that it is like one of those complicated Renaissance clocks where on one level an allegorical marionette pops out to mark the day of the week, on another a skeleton death bangs the quarter hour with his scythe, and on a third the Twelve Apostles do a cakewalk. The variety of the sideshow distracts one’s attention from the advance of the hour hand.” -A. J. Liebling We plan for the things that we know will happen rather than the things we don't know will happen; and yet, we don't know much of what will happen. We can create space for more than we ourselves have imagined by carving out an empty, unplanned space, and merely observing what exists there. Filling our heads with these sights and visions, we will have thoughts we might not otherwise have had and come to insights that would have been lost to us based merely on our already-experienced and meticulously-planned base of knowledge.




Christian Busch, a leading researcher into the cultivation of serendipity, shares some techniques that can serve as "serendipity hooks" in conversation. Such phrases are intended to elicit from your conversation partner answers that must be individual and off-script—answers that you cannot guess before you hear them. [An opposite example would be a question such as "How are you?" or an answer like "I am a doctor," which tend to elicit more of a limited range of responses]. Busch suggests planting very specific strains of information with a new business acquaintance or stranger and seeing what emerges. He gives an example offered by a London-based entrepreneur named Oli Barrett: Question: What do you do? Oli's response: “I love connecting people, have been active in the education sector, and recently started thinking about philosophy, but what I really enjoy is playing the piano.” Notice that Oli has offered a diverse smattering of information, any one of which may—by chance—apply to something in the life of the unknown questioner. As such, the opportunity for serendipity has increased by a significant percentage.

  • A passion (connecting people)

  • A vocation (education)

  • An interest (philosophy)

  • A hobby (playing piano)

Consider offering similarly detailed information in a variety of categories the next time you are presented with a rote question, and perhaps you will find that your conversation partner will latch onto one of the specifics with a passionate response of their own!



Especially in light of the events of the past year, as the entire globe has raced to develop a vaccine with a very singular goal in mind, it is important to contemplate the long-standing discoveries that occurred by accident at one time and may have prevented perpetual calamities in a future one. If we keep this in mind, we might convince ourselves to maintain an alertness for the unexpected and a solution- and curiosity-based mindset, unencumbered by the duress of imminent danger but amidst an atmosphere of leisure and opportunity; this is as true and as significant in our individual lives as it is with regard to discoveries that impact the broader global body of knowledge. Let's take a look at some of the most interesting cases of serendipity in the history of invention: SUCRALOSE In this story, a somewhat humorous accident falls upon an individual through (presumably) no fault of their own; it is the "re-framing" of this mistake as useful that becomes significant and renders the episode itself "serendipitous." In 1975, a scientific collaboration occurred between King's College London and the Tate & Lyle sugar company. The goal of this unlikely pairing was the development of an insecticide using sucrose (sugar) as a component in a chemical reaction. A graduate student on the project, Shashikant Phadnis, was told to "test" the insecticide substance—but instead, misunderstanding the instruction, he "tasted" it! This snafu thankfully led to no ill health effects, as we well know—for he had discovered that the substance we now know as the artificial sweetener sucralose. The team pivoted from the goal of killing insects and instead began to develop the low-calorie sweetener that came to be lovingly known by Leslie Hough, the grad student's advisor, as "serendipitose."

THE POST-IT As 3M reports it, the history of the Post-It occurred due to a failure in adequate adhesive development by one of their scientists, Dr. Spencer Silver, in the 1980s. Silver was appointed to create "bigger, stronger, tougher" adhesives for 3M; unfortunately, his most recent adhesive had the uncanny quality of sticking to surfaces without actually bonding to them. As this was of no use to 3M at the time, nothing may have come of it (despite Silver's insistence to the contrary). The combination of another accident and some sagacity, however, has made it ubiquitous in our daily lives decades later: His colleague, Art Fry, was having trouble with the bookmarks that he used in the hymnals for his church choir—namely, they kept falling out of the book. He needed a bookmark that would temporary stick without permanently damaging the hymnal. Recalling Silver's seemingly useless invention, he approached him with this potential application, and together they began using Post-It notes to leave "texts" for each other around the office... And what was the origin of its iconic yellow color, you might wonder? It was, admittedly, the only color paper they had on hand from the lab next door. PENICILLIN As it is possibly the most famous of science's serendipitous occurrences and the one with the most directly traceable impacts on modern medicine, it seems an oversight to leave this one off the list: In 1928, Scottish biologist Arthur Fleming accidentally discovered penicillin. Having inadvertently left a Petri dish containing Staphylococcus aureus unsealed as he left for vacation, Fleming returned to find that the Petri dish had grown a mold that exhibited a very strange property: bacteria had refused to grow in proximity to the mold. In this, Fleming saw an opportunity, and he wrote up his results for posterity. Ten years later, Howard Florey, a pathology professor at Oxford, built upon Fleming's results to develop a component of this mold—penicillin—that would become one of the most common antibiotics throughout the world. Sir Horace Walpole's insistence on sagacity seems to be paramount here: Had Fleming not been alert to the positive ramifications of his accident and found the courage to embark on a new line of inquiry rather than re-routing himself to his original course (or, perhaps even worse, hiding his supposed failure), he would not have been the one to discover penicillin. It is true that most likely, someone down the line would have, but he as an individual would not. In fact, reportedly, 28 scientists before him worked with the same colonies of bacteria, but deemed the wayward results anomalies and moved on.

"Serenflipity" [Immersive card game] This adventure "game" is available as a card deck and also as a beta text format. It comes with 30 adventurous activity cards that provide you with "missions" to put you in the path of serendipitous occurrences in the real world. "Serendipity as an emerging design principle of the infosphere: challenges and opportunities" by Urbano Reviglio [Original research paper] This paper contains a very readable and useful history of the conception of serendipity from the history to the present day, and it presents instances and the importance of its integration into the design of digital information delivery (namely, the internet and social media).

"Five Life-Changing Chemicals Discovered by Accident" (C&EN Media Group) Though many sites chronicle some of the accidental discoveries listed here, this site provides a greater level of detail about the human and historical context surrounding the discoveries—that, and a bit of narrative flair! "How to be Lucky" by Christian Busch (Psyche/Aeon) In this well-organized article, Busch shares many of the insights from his book The Serendipity Mindset: The Art and Science of Good Luck. He shares his serendipity cultivation technique of trigger/connect-the-dots/sagacity-and-tenacity with clear advice and discusses concepts such as hindsight bias and functional fixedness.


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