The Lost Art of Chance: Rediscovering Serendipity in a Curated Age

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Serendipity in the Smartphone Era How to Court the Unexpected
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  • Technology platforms anticipate our needs, but risk eroding serendipitous moments.
  • Psychological studies and historical breakthroughs show how spontaneity fuels creativity and problem-solving.
  • Breaking algorithmic predictability by varying digital habits and embracing unplanned encounters reawakens curiosity and new perspectives.

The funny thing about life on algorithms is that the social media platforms we use everyday know what we want to see before we do. Maybe we're predictable, or maybe the habit-driving behavior tech breeds make us more predictable. They know which of our favorite groups we're going to check on before we think to look for them. Predictive features on Uber can anticipate where we're headed. Music-streaming platforms know which playlists on our heavy rotation are going back on the headphones.

By leaning into our daily habits, technology reduces the friction between everyday decisions and getting the mission done as efficiently as possible. Yet for all that efficiency we're losing a bit of serendipity. Neuroscience tells us that spontaneous play is critical for brain development, which is particularly true for children. But passive user habits create a toxic relationship with technology that deprive human life of spontaneity.

Serendipity by Kenichiro Nishihara

I.

Originally coined by Horace Walpole in the 18th century, serendipity was inspired by the tale of "The Three Princes of Serendip." The myth paints a picture of gentlemen who, through happy accident and spontaneity, often found themselves in the path of unplanned discovery. A notion that continues to be popular in the tech sector today when discussing meaningful accidental breakthroughs. The advantage of serendipity in the tech space is that often we're looking to solve problems that other people don't even notice are there. And in the pursuit of such ends, the path to writing new answers to unrecognized problems can seem invisible. Spontaneity gives us an opportunity to see our problems from a fresh angle we haven't considered yet.

Serendipity is something that happens naturally in face-to-face office practices. But with remote work on the rise, tech corporations are scrambling to recreate water-cooler conversation that lends itself more accessible to good luck. For example, Google's in-office norms were designed to maximize "causal collisions" among staff members. Microsoft attempts to expand this to remote workers by including similar features in their Azure platform to boost virtual serendipity. Even platforms like Donut, a slack integrated app, randomly pairs workers together for sudden coffee chats. A feature that introverts might find terrifying, but nonetheless create a space where employees are more likely to share information with someone that could become flash inspiration.

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The beauty of spontaneous interactions and serendipitous happenstance is that they lend themselves to more creative problem-solving. The ancient Greeks define the fallacy of bifurcation as insisting that the only possible solution to a problem must be one of two options. In a work environment where nerds just do things because "that's the way we've always done them," you're not fostering an environment for innovation. By allowing for fresh takes from new angles teams are able to take more dynamic approaches to problems that seemed difficult in a 2-dimensional way before considering its depth from another direction.

Throughout history philosophers have given their two cents on the importance of allowing space for the benefits of serendipity to manifest. Epicurus posited that random atomic "swerves" open new possibilities in an otherwise deterministic universe. Thus an ancient Greek notion on the marriage between chance and creativity was born. And you might be surprised to find out that Francis Bacon, father of the scientific method, was game for the reward of spontaneity. He compared knowledge acquisition to hunting where researchers must foster the circumstances that enable unexpected "game." Bacon believed that, under the right conditions, more meaningful discoveries could be made through the innovative process of spontaneity.

Psychology also praises the advantages of serendipity. A study by Judith Mildner and Diana Tamir shows that mind-wandering improves memory efficiency and problem-solving. Spontaneous thoughts not only optimize memory, but helps recombine memories in novel ways. And if you've ever seen an episode of House M.D. you know that's a massive advantage for creative problem-solving. The same study found that 47% of day-dreaming surrounds goal-relevant thoughts. While day-dreaming may seem like a completely random cerebral movement, your ego narrative is never completely suspended. And your mind is subtly getting closer to solving problems intuitively even when you're wandering aimlessly through your mind.

a woman is laying down in the snow
Photo by Robin Edqvist / Unsplash

II.

Are your tastes curated by you, or for you? Digital algorithms can make a case that they've defined your style, at least in part.  Eli Pariser called this phenomenon "filter bubbles." Recommendation engines become self-fulfilling prophecies after they've pegged the type of consumer you are. And you get put into a convenient box for platforms to advertise to you. The more your decisions start to mirror the algorithmic suggestion the more your relationship with tech becomes an echo chamber. As streaming services, social media, and e-commerce continuously numb you into a passive personality molded by suggestion the less you'll need the creative ideation that comes with spontaneous thought. It's almost like the machine starts to take care of that part for you, effectively atrophying the creative muscles in your mind. The more convenience leaves you vulnerable to algorithmic suggestion based on your previous tastes the less likely you are to be exposed to serendipitously diverse content from new sources.

Homogenous mental patterns can be a cancer to the creative mind. Think about what happens when AI does it. The cannibalistic feedback loop of AI training on AI-generated data leads to model collapse. Likewise, you're not doing your social life or intellectual growth any favors by repeatedly revisiting past preferences just because you're constantly reminded to by a machine to optimize ad campaigns.

Take the polarized politics in the U.S. Things couldn't seem more divided. But that could be do in large part to filter bubbles. Political echo chambers deepen ideological divides by isolating users in self-reinforcing feedback loops. It's no surprise that folks exposed to only politically aligned content underutilize the brain's capacity for empathy, and are less likely to compromise or participate in constructive dialogue.

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Chronic cyber individualism can also lead to erosion of collective reality. As people are fed hyper-personalized content confidence is lost in shared societal narratives. Which can severely undermine institutions that live off of that collective confidence such as democracy. That mistrust turns into conspiracy theories and misinformation which can be particularly dangerous for our society. Especially in situations like the Covid pandemic in 2020.

So how do we gently "break" algorithms to free ourselves from inbred ideas? In a nutshell, never let them know your next move. Try browsing unfamiliar genres on streaming platforms. Switch up what apps and tools you use since that activity is being monitored by algorithms. Explore new voices online by subscribing to newsletters and social media accounts outside your usual haunts. Delete apps that encourage repetitive behavior. Even if it's temporary until you need the app again. Avoiding that repetition, even for a short period of time, could remove you from the hamster wheel for long enough for it to feel meaningful. This digital-wandering is an intentional randomness added to your cyber life to avoid falling into predictable patterns. Because predictability is the enemy of serendipity, and an enemy of the serendipitous is an enemy of the imagination.

MIX THAT SH*T UP

III.

Serendipity has given us some of the greatest minds, and solutions, in human history. Physics wouldn't be in classrooms today if it weren't for Sir Isaac Newton being attentive to an apple suddenly falling on his head. Alexander Fleming would've never given us medicine's first antibiotic if he hadn't accidentally left out some bacteria in petri dishes that got executed by mold. Having to be his roommate would've been a nightmare though. If Percy Spencer hadn't noticed his radar experiments coincidentally melted chocolate then we might not have microwave ovens. And if Albert Hofmann hadn't accidentally ingested lysergic acid then music festivals just wouldn't be the same.

The world just wouldn't be the same if some detail-oriented scientists hadn't taken the time to notice observations outside their pay grade. Seemingly useless information suddenly becomes a transformative innovation for society improving quality of life for all. Or in the case of Hofmann, the psychedelic quality of their high.

IV.

Society often paints curiosity as the passive quality of a growing child. But curiosity deserves to be held in high esteem as an intentional discipline. By cultivating a habit of asking "what if?" and staying open to new information, even if and especially when it seems unimportant, could be the difference to an alternate timeline of innovation. A certain level of comfort has to come from embracing ambiguity. Uncertainty becomes less of a threat and more of a fertile space for discovery.

Create environments that make serendipity inevitable by organizing events with friends to share unplanned encounters. Set aside time where you move without a plan. Set the phone to do not disturb and just engage with the world with no agenda. Soak in the details, and don't forget to daydream.


by Derek Guzman

Independent journalist in tech, art, and philosophy

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