Mar 13

Serendipity, so what?

(Note: This is last piece of a larger exploration I’ve been working on around serendipity. You can find all the articles here.)

So, I think this will be the last post about serendipity (for a bit anyway.) I looked, and I’ve written more on Serendipity in this blog over the last few weeks than I wrote most of last year. It’s been fun to write and explore ideas again. I hope/plan to keep this cadence up. Exploring ideas through writing is good for me; I’m too easily distracted otherwise. But enough about that. 

So after reading and writing about serendipity for the better part of 5 months (obviously a lot more reading than writing), I was left to wonder where it’s taken me.  Serendipity is this ethereal concept, and you can’t really plan or program for it. You can position and prepare for things, but there’s no assurance. I was wondering about all this a few nights ago. At the outset, I was excited about this magical nature of luck, but now that I know much, much more what changes? Sure it’s good dinner conversation, but what could anyone take from this? 

I think I’ve decided that serendipity is probably more about the journey than the spoils it might reward. Adopting a lot of the practices to move you closer to serendipity probably leads you to a more interesting, fulfilling, waking life. If we all found inspiration at the edges of our network, or worked toward a beginners mind, or built our world our passions, or were generous with everything we had to offer we would shake off a lot of the cynicism and weariness we earn with age and experience. And after prying these barnacles off our mental bow, we might see new waters.

I’ve also noticed that the principles behind serendipity have huge parallels with the processes of creativity and design; learning through making, finding inspiration anywhere, provoking thought through action. In this same way, serendipity is more of a means than an end. Because of your creative process you see and create new things. You won’t know where you’ll end up, but the process helps your mind move through things. (I’m left wondering is you can sharpen and tune your process for serendipity in the same way you your creative process.)

As a process, serendipity lays out some principles for a life best lived. It’s not a quid pro quo existence. It requires a faith in something bigger; faith in people, faith in the greater human potential. This for me is probably the big idea. If serendipity only occurs in 1% of our lives, its principles set us up brilliantly to experience the other 99%. The idea invites you to be more open, more curious, more engaged, and more generous. And we can’t encounter serendipity alone, we need each other to stir our thoughts. We have to trigger each other’s soft machines.

So, if we’re pursuing serendipity, we’re better together. This more networked and messy process flies in the face of some of the capitalistic and objectivist tenants infused in our culture. I’m sort of excited to see serendipity popping up so much in the zeitgeist. Hopefully we’re moving beyond the selfish idea of luck and the collective concept of potential.

Mar 13

Big Enough for Luck

(Note: This is a piece is part of a larger exploration I’m working on around serendipity. You can find all the articles here.)

It occurs to me that it’s really hard for serendipity to strike when you’re tackling small or easy problems. In fact, serendipity seems to show up when people struggle with really large, almost unsolvable problems; challenges so big that you start to look in new and novel places for new inspiration.

In thew spirit of solving really big problems and inviting serendipity, Google has created Google X. It a lab where they create programs known as “moonshots”, (I think in reference to Kennedy’s decision to go to the moon.) These moonshots tackle problems that are so difficult they will take years to accomplish. This is how a search company can manage to launch a self-driving car, or consumer heads-up displays. They’re putting some of the brightest minds in the world on these problems, but they’re also slaving away for long periods. It’s the duration that’s interesting to me….the longer slog seems to invite more moments of serendipity

I think to really engage the creative, pattern-spotting portions of our brains we have to solve problems that are big enough to invite some struggle. Framing a problem where you’ll probably fail, where you have enough passion to start again, and where there is no correct answer from the outset, these are the challenges that invite serendipity. 

Feb 13

The Double Bind

(Note: This is a piece is part of a larger exploration I’m working on around serendipity. You can find all the articles here.)

One of the more important points I happened upon during all this research is the idea of the double bind. It was the closing thought to one of the more enlightening pieces I’ve read on this topic.

A double bind is when someone feels the logical and emotional weight of being asked to choose between two contradictory ideas. And more than a simple a-or-b choice, the person feels an extra anxiety because either choice feels incorrect. For example, “choose a direction, but remain open to spontaneity”. The question fails you before you can even answer.

These sort of challenges are embedded in every part of understanding serendipity. It’s probably the root principle that makes this topic so easy to understand, but so hard to explain. It’s also what makes serendipity such a human experience. It’s sort of it’s own kind of faith. This passage really struck a chord with me:

In truth, many circumstances that seem irreconcilable are actually two-sided situations that we need to learn to embrace, not suffer through. Instead of treating them as opposing forces, planned serendipity teaches us to view these two sides as complementary.

That’s how designers think. They bring harmony to what seems to be opposing ideas. This inspired me because I’ve felt like the recent popularity of design has robbed it of some of it’s magic. Not the ‘dark arts’ kind of magic, more the mental judo described above. Seeing the parallels that link serendipity and design remind me that design is also a fundamentally human exercise. It also reminded me that good design still has a bit of magic to it. (And that made me smile.)

Feb 13

Mindful Mind Tricks

(Note: This is a piece is part of a larger exploration I’m working on around serendipity. You can find all the articles here.)

So far in for this series, I’ve tried to write a bit about how to foster serendipity through personal interactions. Then we looked at how networks can effect how we connect to new information and ideas. For this post I’m going to explore how our own mindset can encourage or eliminate the possibility of serendipity.

The Approach Pattern
Serendipity is an exercise in perception. From the thoughts in your mind, to the stimulation of your environment, you are digesting vast amount of data and your mind is constantly sorting things out. To paraphrase Glauco Ortolano, ‘Serendipity is about finding something you didn’t know you were looking for.’ In that spirit, *how* you solve your problem is as important as *which* problem that your solve.

As a designer, when we’re tackling a problem in the studio, it’s quite common for us to distinguish between design and analysis. A design mindset is generative; when you’re in that frame of mind you arrive at an answer by creating more and more options until you see a pattern that moves you forward. An analytic (or reductive) mindset assumes that you have all the options in front of you and you need to choose the best option to proceed. The former will leave you with tons of new ideas (some good, some not), the latter will deliver a thoughtful recommendation selecting the best option available. It’s a simplified scenario, but even thinking about this comparison illustrates that a significant difference in problem solving.

Taking this exercise and applying it to serendipity, we can see that we’re going to fare far better when we’re creating and recombining new ideas. To get to something new, we need to remain curious and explore what could be. (In some sense, our actual moment of serendipity is a little bit like that  pattern recognition moment from the previous paragraph…only we can’t plan when we’ll spot the pattern.) So, err’ing towards generative exercises and playing with ideas encourages your mind to be in the remix mode you need to stumble into that new juxtaposition. This is probably not surprising, but when you consider most businesses become successful by hiring really smart, really analytical problem solvers, you’ll see that adopting this frame of thought is easier said than done. 

Distracting Rewards
Beyond how we entertain ideas, our motivation to solve the problem really frames how we approach the challenge. I won’t spend much time here because the bookshelves and business rags have beat this topic to death and Dan Pink’s book Drive (here’s a great summation) probably make the quickest work of lots of research with similar findings. The bottom line is that when people think they are solving a problem for money or other extrinsic motivators, they have a tougher time coming up with creative answers. Challenges that offer rewards literally change the way people think about solving a problem. (yet we all work for some sort of money, so this is a hairy problem.)

Blind Faith
Since serendipity is act of faith, we’ll probably be best primed to experience it by starting with little leaps of faith in our own lives. This could be a small exercise, letting a stranger choose your restaurant and your dish for dinner, or boarding a city bus without knowing the destination. It could be a larger act, like moving to a city without knowing anyone and having no job. The point is, when you place yourself in these moments something will happen (you just have no idea what). And in this moment, it will be up to you to make the best of things. It’s an exercise in optimism and in finding value in the unexpected. In these cases, there is no better or worse choice; it’s all unexpected.

Through these exercises, we learn the value of being uncomfortable and the act of letting go. We’re forced to embrace moments when we just don’t have an answer, a right answer doesn’t exist. This is when we the spiritual side of serendipity starts to show up. There’s a confidence that things will work out, we’re just not sure how. You’ve created a small, safe space. Now move this same idea to a small exercise at work…rinse, repeat, scale.

The Dangers of Satisfaction
To hold a modern technology lens against this point of serendipity, you can probably guess what I’m wondering about. We live in a world where answers are always at our fingertips and we’re primed for immediate resolution. Our dopamine receptors are raging from all this immediate satisfaction, but our creative mind struggles because while we’re absorbing tons of knowledge, we’re tackling less and less really large problems, (that my perception anyway).

There’s that old chestnut about the mind being a wonderful servant and a terrible master, (it’s also my favorite DFW piece). To set yourself up for serendipity, you’re going to have to think about how you’re thinking. And my guess is that it’s going to be a little difficult at first, but you’ll get the hang of it. BTW, if you’re in the market for creativity exercises, Dan Pink’s A Whole new Mind is absolutely excellent. (And with that, I reach my limit of Dan Pink references in a single post.) 

Feb 13

Luck & the Network

(Note: This is a piece is part of a larger exploration I’m working on around serendipity. You can find all the articles here.)

It would be impossible to explore serendipity and not spend a lot of time thinking about networks. Even subjectively, we equate people’s connectedness to be an indicator of their good fortune. As you might guess, this is only part of the story. I’m learning that there are some surprising elements of how networks actually foster better conditions for serendipity, here’s a few.

Strong and Weak Ties
So, as is pretty well documented, networks are made up of strong and weak ties. To understand how these ties play with serendipity, it’s good to think about what sort of data flows they facilitate. Strong ties are the deeper relationships that exist in your life. It’s likely that you have similar values as your strong ties, and that they might connect you to new opportunities. As Reid Hastings recently blogged, “if you’re looking for opportunity, you’re really looking for people.”

When we’re searching for serendipity (which is different than opportunity), it turns out strong ties might not be as helpful as weak ties. Because of the redundancy, they become a bad place to look for new stimulus. For serendipity, the weak ties are much more valuable as they’re likely to contain a less considered point of view, or a divergent thought.

As a side note: Through this lens on networks, the design process and the view on serendipity are almost identical. If you want new ideas and inspiration, go to a place you would never expect; you’re looking for extreme examples of style. If you stay with familiar sources of inspiration, it’s going to be very hard to move past previous thought.

For fun, LinkedIn has a great app that visualizes your network based on the connections you’ve created in their service. It’s pretty interesting to see the major grouping and the proportions in your connections.

The Myth of the Maven
One of the more interesting stories I came across in my research was this story of a Yahoo researcher disproving Malcolm Gladwell’s maven concept set forth in his famous Tipping Point text. In 2008, Duncan Watts published a paper that proved that it wasn’t actually a small, powerful group of influencers in that encouraged massive change. The masses basically adopted something when they collectively wanted it.

While this is unfortunate for Gladwell, it leads us to this reminder that networks themselves have a preference, and they collectively filter and promote. In the infancy of the net, it was predicted that one day we would have a great collective discourse that would drive change. Sadly, this never happened, the networks propensity to act as a hive mind leaves us more polarized than curious. So given the limits of our own networks it becomes important to work across many desperate networks.

When we think about how networks filter for content, we’ll do better spending time where there’s a large amount of anonymity and the community acts as a meritocracy. With these principles, you’re dialing down the social influencers and dialing up the influencers based on their ideas. Dribbble, Pinterest, and Svpply are sort of designed to function this way; they allow people to navigate content based on weak ties and function largely on merit (rather than influence.) So these are digital examples that encourage serendipity. While Eric Schmitt is known for referring to Google as a “serendipity engine“, I can’t agree – there’s been so much work to refine and hone that search algorithm, you won’t walk away with anything except exactly what you were looking for.

Growth through Steroids
As we think about how technology is changing how we experience serendipity, one of the first places my mind goes is this explosive growth in our networks. It’s distorting the way we think about the people we know. Casual connections become recorded into permanence as technology helps us track everything.

We’ve blown way past Dunbar’s number of 150 (at least in our online friend metrics.) And thanks to Facebook, the six-degrees of separation is down to 4.74. Beyond the connections, these networks have become social spectacle in their own right as we track each other’s relationships and careers. And as tacit concepts like networks become more explicit, taking on different roles in our lives, we begin to use them for different purposes and distort some of the underlying principles. (See: Klout.com)

Final Thoughts
There’s a consistent “inversion theme” running through most of this research. The things I perceive to be the most important aren’t usually as impactful as what initially appear to be edge pieces. While the network is an important deciding factor of what you experience, what is convenient doesn’t really seem to yield what you hope (the network has an inbred opinion.)

To combat all this, you have to have the natural curiosity to find new inspiration that fuels this recombination that births serendipity. Also, to actively work with serendipity and force new collision means that you always have to work with the meta level; how/why you’re solving the problem you’re working on is as important as the actual problem you solve…

Feb 13

Exploring vs. Committing

(Note: This is a piece is part of a larger exploration I’m working on around serendipity. You can find all the articles here.)

Most of us are pretty familiar with the trade-off that exists between exploring new ideas and committing to a defined direction. We might feel anxiety when it’s time to stop entertaining new ideas and start deciding on a concept to build. There might be this nagging feeling that maybe we hadn’t gotten a great idea so we weren’t going to have a great concept.

The tension between exploring and committing is a big part of understanding serendipity. I had assumed that exploration would have been the favored state. You know, remain really flexible, digest tons of ideas, mixing and mashing them all together until you experience this glowing moment where the heavens open up wit this unbelievable idea. (Yah….ok.)

This whole explore forever mode actually turns out to be the worst path to serendipity, luck happens better through commitment. At the heart of serendipity is this act of recombination; you’re remixing ideas and experiences in your head and in your conversations with others. Through this process you’ll begin to see new patterns and insight. So, as it goes, if every idea you consider is flashy, new and unconnected, it will be hard to see something different in the whole. There is value to stewing in things a little bit. 

Commit and Create
Beyond recombining ideas, it turns out that committing to an idea has a powerful force on your environment. Instead of evaluating everyone else’s ideas, you become a beacon for your own. Lane Becker and Thor Muller lay it out perfectly in their book Get Lucky*:

Commitment, an essential skill of planned serendipity, involves organizing ourselves around an overriding purpose. Commitment means having a point of view that’s so strong and expressed so powerfully that it actually transforms the environment around us. In turn, our commitment stirs up latent desires and intentions in those who work with us, inspiring in them the conviction they need to act on those intentions in situations where they otherwise might not have. When we are fully committed we serendipitously run into things already on our path and recognize opportunities uniquely suited to us, even as others miss these opportunities completely.

This sort of blew my mind. It’s completely obvious, yet the nuance is important. In the past, I’ve written about the power of committing to an idea. But I had argued for commitment in order to psych yourself up for a gnarly challenge, or work through a problem by sketching your ideas. I hadn’t considered how much committing might help shape your environment, which is such a powerful idea. It’s human nature for people want to help others, and this type of commitment plays right into our best intentions. Herein lies the power of co-working spaces, meet-ups, communities of all sorts. Life has the chance to become a self-fulfilling prophecy of the best kind.

The Perils of the Pivot
So along with just understanding how serendipity might occur, I’m trying to think about how our rapidly changing environment might change the way we experience serendipity. You can probably see where this is going. If we can build and test ideas faster than ever could this rob us of the opportunity that a longer-term commitment affords us?

The tech start-up world is littered with these stories of companies who pivoted to brilliant ideas, and we don’t often here the stories of the unsuccessful pivot (mostly because the company didn’t live to tell the tale.) Choosing to explore an idea or commit to a direction is an important question to return to often. It’s also important to not overlook how much a bold commitment might create more opportunities than endless exploration.   

*Muller, Thor; Becker, Lane (2012-03-09). Get Lucky: How to Put Planned Serendipity to Work for You and Your Business 

Feb 13

Dissecting Serendipity

(For the next few posts I’m going be sorting through some thoughts on Serendipity. I proposed a panel around the topic because it seemed like a good way to force myself to dig deeper into the idea. You can find all the articles here.)

Where to begin?
Serendipity is a difficult idea to wrestle with. On the surface, it’s a fortuitous turn of events that leads to an unexpected outcome. The mechanics that create this turn of events are much more nuanced and complicated that you might expect. The existence of serendipity is indisputable, yet it’s occurrence is unpredictable. So much of our behaviors and culture are built on the idea of serendipity, it’s probably worth digging a little deeper. (There is that idea of blind luck, like buying a winning lottery ticket, but that’s not what we’re after here.)

To plow an even field through this topic, it’s probably best to begin at the beginning (sorry). I’ll spare you the etymology and the story about the Princes of Serendip, though I might be the first (almost every piece I’ve read has yet to resist it.)

The Definition
On the analytic side of things, serendipity is a collision in your mind that requires three main ingredients; pre-existing knowledge, behaviors that encourage you to see new patterns, and, most importantly, stimulus that reframes what you’ve known to see something new. An over-simplified equation it might look like this (my apologies to the field of graphic design).


There is an ocean of nuance in each of the pieces of this equation, but these seem to be the main tenants. I’ll dig into the nuance later, but this diagram helps me organize a lot of the axioms around serendipity. First, it builds off what you know. (Which means experiencing serendipity is completely personal; no one organizes all his or her knowledge in the same way.) Second, certain behaviors better prepare you to recognize or invite serendipity. Finally, it’s triggered by an unanticipated experience; so we can’t predict when it will happen, we can only prepare in hopes that it might happen.

At the heart of serendipity is idea of recombination; taking what we thought we know and adding additional inspiration to reframe what we know. In this moment, we might find new insight from past thoughts or a new avenue of exploration. Ironically, because this reframing seems to play on some singular mind chemistry, serendipity isn’t a group experience. But, without the collective to inspire new thoughts, serendipity would be almost impossible.

Beyond the Definition
After we dissect the idea of serendipity into its working parts, it’s really interesting to think about the more spiritual side of the idea. It’s one of those ideas that exists through the magic of who we are as humans and how we learn about our world. To prepare for serendipity invites some of our best human qualities. We need to be insatiably curious, optimistic, diligent, and weather a bit of blind faith – these are the lenses that encourage us to find new perspectives.

Through this research, I’ve found that the process people use to prepare for serendipity is very similar to a design process. Great designers steep their minds in a problem and, through their creative process, tease out something beyond what they knew. They prompt themselves with different stimuli, they share their directions which shapes their environment. They don’t know the end when they begin. Both of these processes invite us to learn and experiment with the intention of arriving at a new idea.

Roger Martin has written about the idea of an opposable mind. He describes an ability in successful leaders to hold conflicting ideas in tension, refusing to let a single idea prevail. (Not surprisingly, artists and designers also work in tensions.) Preparing for serendipity really requires us to navigate tensions in a similar way. To invite Serendipity, we’re asked to…

  • Commit to a direction yet remain spontaneous to new opportunities.
  • Lose ourselves in the problem while retaining some mental distance from the work. 
  • Become an expert in our field while finding patterns outside our industry. 

So this is what I’m working through; I’d love to hear *any* thoughts and reactions. There is no shortage of research and books in this area. I’ll try to note/publish everything I’ve encountered and reference the thinking where I’ve found it. Beyond understanding how to prepare for serendipity, I’m especially interested in its parallels to the design process. I’m also curious in how the way we approach serendipity might be changing in our very connected world (this later interest is the subject of the panel I mentioned at the beginning.)