Latent serendipity

When I was a kid I liked to dress up in the stories of successful people.

I read about how Bill Gates used to rock in his chair when he was thinking, and for a few months after that I made sure to rock back and forth whenever I was programming. I read a book about Stephen Hawking that described how Oxford graduate students would buy huge sketchbooks to scribble physics formulas in, and so I went out and bought a huge sketchbook to carry around with me.

We all do this. We read little snippets of people’s lives in long magazine exposés, or see adaptations of their adventures in 2-hour summer biopics, and we take their personality traits and try them on like a pair of new shoes. Then we look at ourselves in the mirror of our minds and ask: “Does this fit? Do I do that too?”

When it’s something like rocking back and forth in our chair we can usually fudge it and say, “Yeah, I do that.” Sometimes we really do end up doing those things for a couple of weeks. Something in our brains tells us if we’re similar to these people we’ll be more likely to share in their success.

But sometimes, trying on these stories doesn’t work at all. There’s a special class of stories that make our minds come up blank.

You hear a singer say, “Well, my parents always played Aretha Franklin at home so she was a big influence for me.” Or an entrepreneur say, “Well, I noticed early on that customer service was the biggest part of running a successful business, and so that’s why our vision is to help companies do better support.”

It’s like successful people have these little insightful anecdotes that they can use to explain their lives. Things like, “This has always been important to me.” Or, “I noticed this from a young age.” Or, “I’ve always been really interested in this.” These anecdotes, these calcified bits of personal history, carry a certain kind of inevitability about them. Like they were always important, and clearly pre-destined to have a huge impact on the life of the person telling them.

When we hear these things, we think to ourselves, “What did I notice early on that I can use to start my business?” or “What did my parents do that’s going to influence my future success?”

Usually, we don’t have an answer. Our brains say, “Your parents never listened to Aretha Franklin.” Or, “You never noticed that customer service was important when you were a kid.” There’s nothing obvious about our daily lives that will inevitably lead to our future success.

Why is is this? Why do we feel like we don’t have this special kind of story to tell? Why can’t we talk about these obvious parts of our lives that will inevitably lead to our success?

And, if we don’t have them, how did these successful people get them? Is it causational? Are they successful because they’ve always known what was “unique” about their experiences that they could apply to their lives? Or is something else going on?

A step into story telling
To answer these questions the first thing we have to do is think hard about how stories work. A good way to do this to look at how some of the most popular stories are constructed: Hollywood movies.

Hollywood movies are split up into three acts: in act one the hero is confronted by a problem, in act two the hero is almost (but not quite!) destroyed by this problem, in act three the hero conquers the problem in an act of unlikely redemption. This forms what we call a narrative arc: it’s a story that is told in such a way that it builds tension and emotional attachment, gets us onto the edge of our chairs, and then resolves the tension nicely and neatly at the end for everyone to live happily ever after.

As Kurt Vonnegut said, “Somebody gets into trouble, then gets out of it again. People love that story. They never get tired of it.”

In all of these stories, there is also generally something special or unique about the character that happens in the beginning that becomes helpful to them later on in overcoming the adversity they will eventually face.

What’s interesting is that if you look at how we write stories about entrepreneurs, or singers, or writers, they’re generally written in the same way as a Hollywood movie.

We like to talk about their lives in a nice neat narrative style. The character usually faces a problem: “I was rejected by 25 different publishers before one took a chance on me.” And the stories are scattered with these same anecdotes that we’ve been talking about: events at the beginning that foreshadow their later success. “I was a big fan of Star Wars growing up, so that’s why I decided to set my novel in space.”

The problem with telling stories in this way, however, is that if you actually followed someone around who was in the process of becoming successful, their lives would look very different from what we might imagine from watching a Hollywood movie or reading a story about them.

A peek behind the curtain
The first time this was really driven home for me, I was reading an article about my friend Noah Ready-Campbell. After college and a stint at Google, Noah started über-successful women’s second-hand clothing startup Twice. Founded in 2012, they’ve grown extremely quickly and recently raised an $18.5 million Series B led by Andreessen Horrowitz.

The article was in the Wall Street Journal and it was basically a question-and-answer format interview between Noah and the journalist. One of the first questions she asked him was:

“What do you know about the market for women’s secondhand clothing?”

It’s a pretty obvious question to ask – especially to a guy who co-founded a fashion startup that focuses on women. Noah replied:

“I went to boarding school in New Hampshire for high school and I was on financial aid, but I had to wear nice clothes every day. I used to go to the Salvation Army. I remember one day buying a Brooks Brothers shirt. Still had tags on it. It was a $200 shirt, and I got it for $10.

I remember thinking it was an incredible deal. That experience growing up gave me a little bit more insight on [secondhand fashion] than probably your typical entrepreneur in Silicon Valley.”

What I found interesting reading that quote is that it contained exactly this kind of story that we’ve talked about being part of every success story – the kind of special characteristic or experience that the character has at the beginning that foreshadows their later success – but I could read it in two different ways:

1. As someone who’s known Noah in some capacity since before he started Twice
2. And as my younger self, reading a story about an entrepreneur I admire

Reading the story as my younger self I would have pictured it in the same way as it would be portrayed in a movie: Noah growing up with this big enduring insight about the price of second-hand clothing firmly fixed in his mind, and who pretty much always knew he was inevitably going to found a company like Twice.

But knowing Noah, I know that Twice is far from the first thing he’s worked on. I know that he’s had many insights throughout his life, and that most of them had nothing to do with second-hand clothing. I also know that the vast majority of his experiences (obviously) didn’t make it into this interview.

Looking at his story from both angles it seems clear there are lots of things that this Hollywood-style of story telling leaves out about our lives and experiences. Interestingly, this is an issue that people have been struggling with for a long time.

Modernism, Woolf, and Nassim Taleb
Around the beginning of the 20th century a movement of writers – the modernists – began to realize exactly the issues with traditional narrative form, and began to question whether this was actually the best way to tell stories.

At the time, novels followed the same kind of neat story arc as the Hollywood movies of today. But the modernists realized that life doesn’t really feel like a Hollywood movie as we’re living it. They thought that authors were just writing novels in the traditional format out of habit – not because it truly reflected the experience of living.

Virginia Woolf, one of the most well known of the modernists wrote:

“The writer seems constrained, not by his own free will but by some powerful and unscrupulous tyrant who has him in thrall, to provide a plot, to provide comedy, tragedy, love interest…The tyrant is obeyed; the novel is done to a turn. But sometimes, more and more often as time goes by, we suspect a momentary doubt, a spasm of rebellion, as the pages fill themselves in the customary way. Is life like this? Look within and life, it seems, is very far from being ‘like this.’”

Woolf argued that life doesn’t follow a regular narrative structure. That’s too convenient, too clean, too easy to digest. Instead, she wrote:

“Life is not a series of gig lamps symmetrically arranged; life is a luminous halo, a semi-transparent envelope surrounding us from the beginning of consciousness to the end.”

Instead of dressing it up with idealized narrative and pre-defined plot structure the modernists created a form of literature that attempted to deal more closely with human existence as we actually experience it.

One of Woolf’s most famous works is a book called Mrs. Dalloway. The plot – if you can call it that – follows an eponymous London socialite from morning to evening of a single day as she gets ready to host a party.

No details are left out. For example, we watch her walk to a flower shop to buy an arrangement for the party, and listen to the things that pop in to her head as she walks. It’s essentially just a collection of moments written as they happen, and it’s actually one of the earliest examples of a novel written in “stream of consciousness” form.

What’s the difference between Woolf’s stream-of-consciousness style and Hollywood movies? A Hollywood movie is written in retrospect. It’s stripped of unimportant moments – every scene has a “reason” for being included, every moment pushes the story forward or foreshadows what’s to come.

By contrast, Mrs. Dalloway is full of “unimportant” details – just like life is. Woolf doesn’t care what’s going to be important to the story later. She just talks about everything that happens, as it happens.

When we talk about success, we tend to talk about it in a Hollywood style – leaving out everything that seems unimportant. When Noah talked about that moment in the thrift shop, he didn’t walk us through a minute-by-minute account of his high school expeirence. Instead, he gave us a one second clip of his early life that related to the company he later when on to found.

This makes a lot of sense when you think about it. It would be terribly inefficient for an entrepreneur to tell a reporter about everything that ever happened to her in high school in order to explain how she gained the one insight that helped her found her startup. And it would also be terribly inefficient for her to remember much less be able to talk about it all. Author, financier and philosopher Nassim Taleb tells us:

“Events present themselves to us in a distorted way. Consider the nature of information: of the millions, maybe even trillions, of small facts that prevail before an event occurs, only a few will turn out to be relevant later to your understanding of what happened. Because your memory is limited and filtered, you will be inclined to remember those data that subsequently match the facts.”

And importantly, this distortion results in a particular kind of survivorship bias: everything that seems irrelevant to the story becomes totally invisible, completely left out. It’s hard for the person who experienced those things to remember them. And the person reading their story assumes that the irrelevant facts don’t exist.

This seems like it answers most of our questions. When we tell stories about success and we leave things out that are irrelevant, we make everything look much neater, more story-like and more inevitable than they would otherwise. This accounts for much of the differences that we’ve been discussing between “success-as-it-is-experienced” and “success-as-it-is-talked-about-later.”

But does this really solve everything? Is all of this just a combination survivor bias and hindsight bias rolled together?

I don’t think it does because it doesn’t deal specifically with how pieces of our lives become important. It still assumes that importance is static – that the significance of everything that happens in our lives is always clear. As though the first time our singer listened to Aretha Franklin she could immediately list her as the key to her future success.

Clearly, there’s still something else to be addressed here.

Retrospective coronations
In his book on evolution, Darwin’s Dangerous Idea, the philosopher Daniel Dennett writes that there are certain events in nature that have a unique attribute:

“You can’t tell that [the event] is occurring at the time it occurs! You can only tell much later that it has occurred, retrospectively crowning an event when you discover that its sequels have a certain property.”

An example of this kind of retrospective coronation, Dennett says, can be found by thinking about the woman who scientists call Mitochondrial Eve – so named because her mitochondria (the energy sources for the cell which are passed down from mother to child) are present in every human being currently in existence.

Paraphrasing Dennett, let’s think a talk more about Mitochondrial Eve by thinking how she got her title:

Consider the set of all human beings currently alive. Each person alive today was born of one mother. Each of those mothers has one mother – the grandmothers. Each of those grandmothers have mothers and so on.

The sets get smaller each and every generation until they contract down to one person: Mitochondrial Eve, the “woman who is the closest direct female ancestor of everyone alive on earth today.”

Dennett asks, how does a person go about becoming Mitochondrial Eve? Was there something special about her? If we had a time machine and could go back to visit her, would we be able to tell that she was going to be the most recent mother of every human alive today?

According to Dennett the answer is no. And it has nothing to do with our ability to gather information. It’s not a question of better microscopes, or more careful observation. “It is important to remind ourselves that in all other regards, there was probably nothing remarkable or special about Mitochondrial Eve,” he writes.

Why do we know there was nothing special about her? Because her current status is a complete historical accident! If things had gone differently at some point in human history, the current Mitochondrial Eve would have had absolutely no historical relevance.

For example, consider a scenario in which tomorrow a plague spread after which only 1% of the population survived. “[The survivor’s] closest common direct female ancestor…would be some woman who lived hundreds or thousands of generations later than [the current Mitochondrial Eve], and the crown of Mitochondrial Eve would pass to her, retroactively…This historically pivotal role is determined not just by the accidents of [Mitochondrial Eve’s] own time, but by the accidents of later times as well. Talk about massive contingency!”

Consider another example (also from Dennett): Imagine a doctor coming home from the office and telling his wife, “Guess what I did today! I assisted at the birth of Victor Hugo!”

There’s something clearly absurd about that. Obviously, the birth of Victor Hugo was not significant at the time it happened. It only became significant much later.

Connecting the dots backwards
So let’s think about how this ties back in to what we’ve been talking about. We know from the modernists and from Taleb that we enforce a story-like structure on to events to make them easy to digest and that, in order to so, we leave out everything that seems “unimportant.” And we know from Dennett that there are events that have a special property: we can’t know they’re important until much after they have occurred.

How can we relate that back to these little insightful anecdotes that successful people share, like hearing a singer say, “Well, my parents always played Aretha Franklin at home so she was a big influence for me,” or an entrepreneur say, “Well, I noticed early on that customer service was the biggest part of running a successful business, and so that’s why our vision is to help companies do better support.”

Maybe the answer is that, like the case of Mitochondrial Eve, there are certain events that happen in our lives that we can’t tell are important until many months or years after they have occurred. And in just the same way that we can’t tell that a particular woman will be Mitochondrial Eve by examining her more closely, we also can’t tell which events carry this special property by paying closer attention – the importance is latent and invisible. What makes them important is their serendipitous connection to what comes later – they are only retrospectively crowned.

You can think about it like this:

Try to imagine every event that happens in your life as a bead. Depending on what kind of event it is the bead gets a different color. As each event occurs you get a new bead, and you throw each bead into a pile of all of the other beads representing all of the things that have happened in your life.

What do you get after living for a few years? A vast pile of beads. Very little structure, very little coherence. Beads of every different color piled together. It might be hard to pick out anything special about your pile by just looking at it.

But now imagine that at some point in your life you get a special kind of bead. This bead marks an important event: you become the first person in your family to graduate from college, you get a big promotion, your novel becomes a bestseller, or your business takes off. Let’s imagine that this special bead is black.

When you get this special bead, something interesting happens: people become obsessed with your origins. They ask, “How did you do it? What was it about your early life that helped you to get this bead?”

In order to explain yourself, you go back through your pile of old beads looking for ones that match it.

And when you look through your vast collection of beads, suddenly the black beads begin to stand out. The black ones didn’t seem special at all before, but now you begin to notice them. It’s sort of like when you first buy a car and you suddenly start to notice all of the other people on the road that have that have the same one – they were there the whole time, you just didn’t notice it.

Sometimes you even notice that blue beads can become black if you look at them right. So you slide the blue beads on to your string with the rest of your black beads, and position them in such a way that they appear black when you look at the string in the light.

When we ask people to tell their stories, we’re really asking for this string of beads.

But what we don’t see when we look at someone’s string is that these beads – the visible beads – aren’t everything. That far from having beads of just one color, the black beads that we see are just a tiny collection pulled from a mountainous pile of beads – the totality of which represents the vast constellation of memories and experiences they’ve had throughout their life.

What we don’t see is the fact that although the first bead on the string is from many, many years ago, at the time they got it they might not have put the bead on a string. It was, very likely, just one bead among thousands of others. Totally mundane. What we don’t see when we look at the string is that it was only much later that the bead became important enough to be picked out of the pile.

Latent serendipity
So what do we do with all of this? What’s the use of seeing the stories we tell about our lives in this way? Is this a pessimistic way of looking at life?

Let’s get back to Noah’s story about noticing the value of used clothing in high school. What’s really interesting is that if you asked Noah today what the big insight from his high school days was, he might tell you that story. And he would be absolutely right – it clearly holds vast relevance to his day-to-day life as a CEO.

But if you had asked Noah while he was at Penn which of his memories from high school would turn out to be most relevant to his future career as an entrepreneur I’m almost 100% certain he wouldn’t have talked about that particular memory.

Clearly that moment changed enormously in significance from the time he was in college to now. What started out as an every-day observation filed away along with millions of others inside of Noah’s collection of beads became something much bigger.

For young entrepreneurs this is a frustrating realization. As young, ambitious people we’re constantly looking for a moment of insight like that. We get these ideas, and we stay up late at night obsessing about them, planning for what the world will look like after we bring them to reality.

But we often aren’t very good at applying this knowledge that the ideas and insights that end up becoming significant often don’t look that way at the time they occur.

This is an important lesson for me, because it applies directly to my story. In December of 2012 while I was still a sophomore in college my dad called me to tell me that he had an idea for a product.

“When I’m on the phone with someone it’s very difficult to explain to them where to go on a website,” he said. To fix this, he wanted to have a grid – kind of like an Excel spreadsheet – expand down from each person’s screen. Then you could tell your friend on the phone, “Look at cell E5,” and you would always be talking about the same thing. He wanted to call it GraphNet.

At the time I think I said something along the lines of, “That’s interesting Dad, but it would be really hard to make it work well on different computers and different browsers. It would probably have to be a browser plugin. I don’t think people would use it.”

I told the idea to my co-founders who built the first version at a hackathon a few weeks later.

2.5 years after that we had built the company that came out of that phone conversation to the mid six figures in revenue with just 2 full time co-founders, a few part time employees and $20,000 in funding. Two months ago, I flew from my college graduation ceremony to finish negotiating the sale of the company to Pega.

Like all young entrepreneurs, I’ve had plenty of moments where I came across an idea and thought: “This is it! I’ve found it. This is going to be huge.” And none of those turned in to anything meaningful. But this small, insignificant-at-the-time little conversation somehow became something very important to my life’s story.

So the first lesson is not to despair at reading these stories. They are excellent inspirational material, but poor instructional manuals. The second is, even though we see it in movies and read about it in magazines it’s not necessary to imbue forced significance on to any particular event or idea as it happens – many successful people didn’t recognize the importance of their experiences until many years after they occurred.

And the third lesson is the most important: whether we recognize it or not the potential for something extraordinary lies in pretty much every moment of our lives, large or small.

It means that each moment carries a kind of latent serendipity – a hidden ability to become something special down the road – if the right combination of events occur to unlock it. It means that the apparent character of a particular moment doesn’t matter. Because ultimately the difference between an important moment and a million others is not how significant it seems when it occurs. The difference is that an important moment happens to produce a spark that doesn’t go out.

And the beauty of it is this: the not-knowing what our story will be requires faith that eventually the beads of our lives will be connected on a string. And it encourages a sense of wonder as we look at every moment – because every moment could be one that becomes woven into the fabric of our life’s story.

As someone flawed, weathered, and wise once said, “You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something – your gut, destiny, life, karma, whatever. Because believing that the dots will connect down the road will give you the confidence to follow your heart even when it leads you off the well worn path; and that will make all the difference.”

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Thanks to Mark Bao, Jesse Beyroutey, Ajay Mehta, Wesley Zhao, Alex Rattray, Quentin Farmer and Paul Singman for reading drafts of this.