How to create serendipity







“How will you go about finding that thing the nature of which is totally unknown to you?” -A Field Guide to Getting Lost, Rebecca Solnit As defined by Merriam-Webster, serendipity is ”the faculty or phenomenon of finding valuable or agreeable things not sought for.“ By definition, only things you don’t seek can possibly be serendipitous. Yet it seems possible to create an environment for serendipity, where unexpected events and lucky meetings are more likely to happen. While researching for this post, I came across a New York Times opinion piece by Pagan Kennedy titled: “How to Cultivate the Art of Serendipity.” I love the question she asks: how do we cultivate the art of finding what we’re not seeking? She’d written a ton of what I wanted to say—down to the etymology of serendipity, which I had researched and already written about. "At its birth, serendipity meant a skill rather than a random stroke of good fortune,” Kennedy writes. But I still have some ideas to add, including a running list of strategies to create serendipity.





First, modern tech problems 🔍

Serendipity is partially responsible for the magnetic pull of social media. Every time I scroll just a little further, I might encounter something funny, or enlightening, or inspiring. Or connect with someone important. Or find a secret opportunity. So why not keep scrolling? Social media has led to serendipitous connections and opportunities in the past, which strengthens the addiction in the same way a slot machine whets a gambler’s appetite. Maybe it will happen again. The internet is gigantic; social media creates the illusion that I’ve narrowed it down to a feed with only interesting or relevant content. Yet “true” serendipity has happened when I’ve made a connection outside of my filter bubble. This is the opposite of social media algorithms famous for encouraging groupthink. Rebecca Solnit writes: “The things we want are transformative, and we don’t know or only think we know what is on the other side of that transformation. Love, wisdom, grace, inspiration — how do you go about finding these things that are in some ways about extending the boundaries of the self into unknown territory, about becoming someone else?”



I definitely don’t feel like I’m extending the boundaries of my self through social media. In fact, it often feels like the opposite. (For example, through creating an online brand and single narrative → see my “Multiple Identities” posts.) For me, social media is still too much of a bubble.





Google 🔍

Google has a different but related problem. Google is perfect at its job; it gives a dead end. I type in a question, it spits out a list of exact answers, definitions, blog posts, and stock photos with bad lighting. I almost want Google to make mistakes: to lead me to something completely new and unexpected. I’m often not asking the right questions in the first place. I want answers that lead me to better questions—the ones I should’ve been asking. I want precise answers sometimes, but random, wild answers at other times. Could there be a search engine that allows the user to adjust the ratio of “types” of results: I type in a word and get 65% exact results and 30% tangentially-related results and 5% completely random results? I don’t think it would “create" serendipity, but maybe the tangentially-related results would yield interesting cross-connections. I was reading the comments on Kennedy’s piece, and came across this one about libraries: As the transition to digital books and journals becomes more complete, where it is more difficult to replicate the browsing experience, it may lead to the decline of this most common of all types of serendipitous discovery. Perhaps [...] [we] can explore how we extend the physical attributes of accidental discovery into an increasingly digital world. (Side note: if anyone’s interested in exploring this idea of extending serendipity into digital spaces, I’d love to talk!)





What is serendipity? 💫



Google is not a serendipity machine, but at least it’s good at generating answers. According to Google, the word “serendipity” was coined in 1754 by Howard Walpole. He was inspired a fairytale called The Three Princes of Serendip, where the heroes are “always making discoveries, by accidents and sagacity, of things they were not in quest of.“ (I tried reading The Three Princes of Serendip, but got distracted and basically came away with: camel, honey, ants, and melted butter.) Going further in to the etymology, the word comes from Arabic Serendib, which comes from Sanskrit Simhaladvipa: "Dwelling-Place-of-Lions Island." This etymology is really interesting to me. The original use of serendipity was referring to heroes on a quest. They weren’t chasing serendipitous opportunities, they were chasing a quest. The word “quest” has been co-opted by dramatic YA novels and video games, but the idea of a quest is quite beautiful at its core: to undertake a journey of searching. People who go on quests know they will be long, dangerous, and painful, but they go anyways. Serendipity appears when you are on a quest—when you are searching for something specific, something transformative. Knowing clearly what your “quest” is helps you recognize and turn unexpected events into serendipity. From another reader comment on Kennedy’s piece: One key element of serendipity is having a problem or question occupying your mind. Serendipity is rarely just random--there is already a direction to it, a focus that is being pursued. So fill your mind with the problem, work it and then allow yourself to not work it. That's when serendipity happens. When there's a structure of some sort already there, a skeleton of knowledge or purpose, that the fairy dust can adhere to. “Fairy dust” is a fantastic way to describe this process. From this quote, I'm reminded of Richard Hamming's speech "You and Your Research":



Everybody who has studied creativity is driven finally to saying, “creativity comes out of your subconscious.” Somehow, suddenly, there it is. It just appears. Well, we know very little about the subconscious; but one thing you are pretty well aware of is that your dreams also come out of your subconscious. And you're aware your dreams are, to a fair extent, a reworking of the experiences of the day. If you are deeply immersed and committed to a topic, day after day after day, your subconscious has nothing to do but work on your problem. And so you wake up one morning, or on some afternoon, and there's the answer. For those who don't get committed to their current problem, the subconscious goofs off on other things and doesn't produce the big result.



Maybe what we call serendipity is really just focus and creativity.



Going back to Simhaladvipa, I’ve also been thinking a lot about this mysterious “island where lions dwell.” If I was trying to cultivate serendipity somewhere, this sounds like a terrible place. As an island, it’s isolated, which isn’t good. It has lions, which also isn’t good (for everyone who is not a lion). But maybe, to create serendipity, I need to seek out the secluded places with lions. I need to seek out places that feel uncomfortable or sequestered. That’s the beautiful part of serendipity—what is startling, magnetic, and unexpected.





Steps ❓



In her piece, Kennedy introduces the term “serendipiter,” originally coined by the writer Gay Talese. Clearly, they don’t teach us in schools to be serendipiters and super-encounterers. So how can we be better at creating serendipity?



Here's a running list of ideas:

1. Mindset

1. Be comfortable with ambiguity and understand ambiguity as a chance to grow/create. (Library of Ambiguity from the Stanford d.school)

2. Love the unexpected and see mistakes as a chance to learn—convert mistakes into positive experiences. “Make your own luck with the unexpected.”

1. A lot of people I admire share past mistakes as a way to show vulnerability and to grow closer with others

1. Some scientific discoveries are said to be made “by mistake.” But the scientist needed to be perceptive enough to notice applications of the mistake and have an open mind to see the mistake as positive

2. Embrace the unforeseen: “an art of recognizing the role of the unforeseen, of keeping your balance amid surprises, of collaborating with chance, of recognizing that there are some essential mysteries in the world and thereby a limit to calculation, to plan, to control.” (From Rebecca Solnit)
3. “You become a super-encounterer, according to Dr. Erdelez, in part because you believe that you are one — it helps to assume that you possess special powers of perception, like an invisible set of antennas, that will lead you to clues.” (From Kennedy’s piece)

1. Seems to be describing a “self-fulfilling prophecy”

2. Believing you are a “noticer” leads you to pay more attention which leads you to become better at noticing









2. Explore

1. Explore is another pretty overused word, usually used in the context of something like: “I’m passionate about exploring stories, tech, and poetry.” (See my own bio). But I feel like being able to list out everything you “explore” shows you aren’t truly exploring. You’re still confined to a bubble of what belongs in a field and sounds nice. Like I wrote in the “multiple identities” posts, if you link yourself with your digital identity, you’ll only “explore” within labels.

2. Instead, I think exploring means having unstructured time to pursue something without a definite metric, goal, and/or definition. This can take on the form of side projects, hobbies, self-studying, etc.

1. Persistent exploration across disciplines, without fear of failure.

2. See everything as an experiment. (Also said by Sister Corita Kent)
3. “Build pockets of stillness into your life. Meditate. Go for walks. Ride your bike going nowhere in particular. There is a creative purpose to daydreaming, even to boredom. The best ideas come to us when we stop actively trying to coax the muse into manifesting and let the fragments of experience float around our unconscious mind in order to click into new combinations.” (From Brian Pickings)
4. “It’s for fun and for other reasons.” -Agnes Várda, see post here. Shows that the “other reasons” are often difficult to articulate, but even “for fun” is enough.






3. Pursue curiosity, wonder, and awe at the unknown. Cultivate the ability to make leaps of intuition and cross-connections. Don’t get stuck in one place or niche

4. Explore physical spaces, especially outdoors or in old districts, and find “islands where lions dwell.”

1. This “explore” section feels weaker and more nebulous to me, I would love to hear other ideas for specific paths to explore in meaningful ways.




3. Pay attention

1. 
   

   

   1. See this post.

      1. “When people look slowly, they make discoveries.”

      2. “Keep your eyes wide open when you walk through a city, or through a room."

      3. “The more ideas we encounter and are interested in, the more likely we are to be enlightened thinkers.”

      4. “Our brain operates more on pattern recognition than logic.”

   2. Take notes, carry around a journal, and write everything down

      1. Create a commonplace book! A written scrapbook to organize your ideas and record details you notice, take notes in the marginalia, remember the best sentences you’ve read

         1. Save everything—it might come in handy later. (From Sister Corita Kent.)

         2. According to Wikipedia, you can write down: recipes, quotes, letters, poems, tables of weights and measures, proverbs, prayers, legal formulas

   3. Notice what is overlooked: first by paying attention, and then by looking from multiple perspectives. Look closely at details and then look from far away.

      1. My dad likes to tell me: if you’re struggling with a problem, look at ground level and then look at sky level (see the bigger picture).

      2. Slow looking — can practice at museums

      3. Look with a finder. (Very high-tech: cardboard with a rectangular hole cut out.) Learn to see and look at the world closely: “It helps us take things out of context, allows us to see for the sake of seeing, and enhances our quick-looking and decision-making skills.” (From Austin Kleon)

   4. Zig-zag to creativity: do opposites and work in the space in-between.

1. A really compelling graphic from this Twitter post by David Perell. Pick two dots on different sides of the circle and try to combine them.






5. Fight distraction, especially digital distraction: attentive resistance

1. (Working on another post about this, will link here)



4. Talk to people

1. This is a counterpoint to my thoughts on social media above: the internet is actually a great way to meet new people with interesting ideas (part of the reason I’m trying to be more active on Twitter 😊)

2. Ask for help, ask questions, ask for opportunities

3. When you explain your ideas, you clarify them and start understanding what patterns interest you

1. People will say: “this reminds me of x” or "you should meet x!"

4. “Talk” to people through writing = writing is thinking

5. Talk to strangers, and talk to little kids

   1. “Part of normal human development is learning to notice less than we are able to. The world is awash in details of color, form, sound — but to function, we have to ignore some of it. The world still holds these details. Children sense the world at a different granularity, attending to parts of the visual world we gloss over; to sounds we have dismissed as irrelevant. What is indiscernible to us is plain to them.” (From Brain Pickings.)

6. “Be generous. Be generous with your time and your resources and with giving credit and, especially, with your words.” (From Brain Pickings.)

7. Talking to people is another form of exploration, serendipitous because of the way our brains work and connections in our neural structures









5. Focus

1. Ultimately, we need to have some kind of “quest”

1. Focus on the “why.” Why are you searching for this? Why did you start this journey and why are you continuing?

2. This is the most difficult component to align and balance. It seems like the “pure explorers” don’t have enough focus to create meaningful serendipity, while the “ambitious” have too much of a focus and don't look around
3. This definition of genius resonates with me: “To live out our genius is to live out the conversation between our particular inherited body and the body of the world from which we seem to have been made.” (From Consolations by David Whyte)
4. A counterargument to focusing: “This state, in which nothing definite is thought, planned, striven for, desired or expected, which aims in no particular direction and yet knows itself capable alike of the possible and the impossible, so unswerving is its power, this state, which is at bottom purposeless and egoless, was called by the Master truly ‘spiritual.’ It is the right presence of mind. Like water filling a pond, which is always ready to flow off again, it can work its inexhaustible power because it is free, and be open to everything because it is empty.“ (From Zen in the Art of Archery by Eugen Herrigel)

2. Requires self-discipline: show up, do the work, read books, go to classes, create a curriculum, review

1. Keep a schedule. I was surprised that in his advice to gap year students, Marc Andreesen only said: schedule everything on Google Calendar. I guess it’s a warning about how quickly time goes by without planning
2. 28-day schedule for creative projects (From Austin Kleon)

3. Patience and a long sense of time

1. Sometimes serendipity is just waiting: “The function of nothing here, of saying nothing, is that it’s a precursor to something, to having something to say. ‘Nothing’ is neither a luxury nor a waste of time, but rather a necessary part of meaningful thought and speech.“ (From Jenny Odell)
2. “Expect anything worthwhile to take a long time.” (From Debbie Milman)



This list is longer than I expected. (Whenever I write a post about what I think is a “manageable” topic, I end up trying to cram in everything I know via like 30 hyperlinks.) But hopefully some part of this is a reminder to anyone reading. Please reach out with any ideas to add to this list, or your thoughts. ☺️



Update 10/1:

Got a tip from @lyoshenka - “Serendipity isn't always active. Just as you can stumble on something, others can stumble on you. For example, your body of work (blogs, tweets, etc) attracts likeminded ppl. So if you want more of that, make your stuff easier to find and you easier to connect with." Think it's a great point to add.

He also pointed me to a David Perell piece on "how to maximize your serendipity." Highly recommend, a ton of new insights that make networking feel less cringy and more interesting. I think it's slowly reforming my idea of Twitter for serendipity (but not social media in general).