Accelerating serendipity

Can you make happy accidents happen more often?

Stef Lewandowski
Makeshift Thoughts
Published in
8 min readAug 13, 2013


Luck plays an unusually large part in any success story—just skimming through a few bestselling biographies will reveal how much people attribute their success to a “break”, a “chance meeting” or a “bumping-into” encounter. That’s serendipity:

An unsought, unintended, and/or unexpected, but fortunate, discovery and/or learning experience that happens by accident.

A combination of events which are not individually beneficial, but occurring together produce a good or wonderful outcome.

Serendipity is often portrayed as just luck—a happy accident that occurs at random. There is a case however, that by having a prepared mind, you will be likely to find more of it. Let’s explore that a little.


The word “serendipity” was first coined by Horace Walpole, an 18th Century British diarist, who wrote about the Persian story of The Three Princes of Serendip (now Sri Lanka), in which three princes went on a journey “making discoveries, by accidents and sagacity, of things they were not in quest of…”

His explanation in his original letter is a little difficult to grasp and is oddly ambiguous. It was only some time later, after his writings were published in the mid 19th Century, that the meaning we now attribute to the word began to be applied.

In the process one thing seems to have been lost in translation from his original observation, that I think still stands true. And that’s that sagacity was involved—a word that has roots in seeking, being observant, wise and keen. And because luck is just random, it’s this side of serendipity that I want to discuss: chance favours the prepared mind. Serendipity isn’t luck.

Can you accelerate serendipity?

Is it possible to increase the chances of beneficial, happy accidents to occur? Can you accelerate serendipity? For the last few years, I’ve been trying, and I’ve bumped into a few principles along the way.

Just turn up

We all get invited to things. When I receive an invitation there’s always a temptation to say “oh gosh, it’s going to be so much effort to get there, I think I have to decline”, or “I’m not really sure what the benefit of attending this is—I think I’ll pass”.

A couple of years ago I was awarded a place in one of those Important List of Young People Who’ll Probably Be More Important in the Future lists—you know the kind of thing.The thing is, I was broke. My bank account was empty and I was down to my last handful of cash. To get to the event I’d be using it to pay for a train ticket.

It was probably slightly crazy but I spent my last penny to go to a party where a bunch of the other people from the list would be. I didn’t know what I would find there, but I was determined that it would be a room full of opportunity. It was. On the way out I briefly chatted to someone who I would go on to found a company with. If I hadn’t gone to that party that wouldn’t have happened. Just turn up became a rule, and it can be applied to any kind of event or invitation—even things you’re not invited to.

Put yourself in the right place

Location, location, location. If you want to bump into people who are relevant to what you want to achieve, put yourself right in the middle. For my new company we wanted to be right in the middle of the London startup scene, so that meant being as close as possible to the famous Silicon Roundabout of Tech City, East London. The bumping-into-ness factor around our studio is way higher than anywhere else in London for the kind of thing we’re doing.

For you, it might be basing yourself at a research park, or taking a desk at a co-working space, or moving to a different city where there’s a higher density of people doing the thing you want to do. Whatever it is, pay attention to the serendipity factor.

Avoid zemblanity

When you’re working, take a break occasionally and try not to lock yourself away for periods that are too long. You can’t work all hours of the day, and bumping into other people is an important factor in making whatever it is that you’re doing a success. Step away from the desk occasionally, get out and speak to people and just turn up.

Zemblanity, a word coined by William Boyd in his book Armadillo in the 1980s, is the polar opposite of serendipity. It’s named after the cold, barren serendipity-less island of Zembla:

“So what is the opposite of Serendip, a southern land of spice and warmth, lush greenery and hummingbirds, seawashed, sunbasted? Think of another world in the far north, barren, icebound, cold, a world of flint and stone. Call it Zembla. Ergo: zemblanity, the opposite of serendipity, the faculty of making unhappy, unlucky and expected discoveries by design.”

I pretty much locked myself away for a few years to build something a few years back and experienced a little too much zemblanity. If there were one thing I could change about that time it would be to have done more to get out and meet people.

Say “Yes, and…” instead of “Yes, but…”

This is such a simple thing to try. Any time someone gives you a suggestion, and you feel yourself thinking of playing the devils’ advocate, stop. Starting a sentence with “yes, but” is a surefire way to close down an opportunity—try to think about the other person’s idea or statement and see what you could add. Start with “yes, and…” and go from there! It’s a principle from the world of improv, and I’m often surprised by the happy accidents that result from a simple suggestion to someone.

Indeed, I’m writing this because of Alex Morris. I’d pulled over to the service station because the road was gridlocked on my journey home. I tweeted that I’d probably not manage my Sunday Post, and he replied, “@stef dictate it into Phone and publish unedited. #doubledare”. Sadly that wasn’t possible, but my “yes, and” was to write it in my head on my way home instead.

Keep your eyes open for opportunity

To paraphrase that famous mis-attributed saying, it’s easy to miss an opportunity if it sounds like hard work. Pay attention to things around you, and you just might find something that,yes, would be hard work, but then whoever made anything of any impact that wasn’t?

Use serendipity engines

Twitter, blogging, all of those social media things that people always talk about, when you frame them as serendipity engines are things that have to go into the mix. I’m not great at using that stuff—I’m mainly just on Twitter, but the rate of bumping-into-ness is radically increased the more you use these things, or so I’ve found.

I’ve certainly found that since starting writing on Sketching with Code, and here on Medium people seem to bump into me more often. By sharing your thoughts online you become more bump-into-able. Because these things are running all day long, I think of them as engines of serendipity that generate a background hum of opportunity.

Don’t be too precious with your ideas

A zemblanitous trend is, when meeting someone, to ask them to sign a non-disclosure agreement about what it is you’re about to discuss. It’s by design, a tool that people use to keep a lid on their idea. If you’ve really got something great, and a patent in the pipeline then, sure, I can understand why you want to keep it private. But I’ve decided not to sign NDAs any more—it’s hard to remember what you’re supposed to know about, and after operating under one for over a year (!) I’ve seen the zemblanitous effect it has on you and the people around you.

Help other people to have serendipity

I tried an experiment—publishing my “free/busy” diary using Doodle. The idea was that people could request a coffee and suggest a time, and reduce the friction in the process. The trouble is, that I found that my days were getting a bit chopped up by having coffee with people. It was impacting on my other work, so I’ve had to reduce that. Instead, I’ve started hosting dinners where I invite the people I would have liked to have had coffee with recently.

It’s useful for the people who attend and fun for me—we all get to meet a bunch of interesting people, as well as having a cocktail or two afterwards. By building in some time into my diary for serendipity I’m hoping to make interesting connections happen. For me and for others. There’s much more you could do here—hosting a regular meetup for your peers, for instance.

Get good at introductions

And while I’m on that help other people have serendipity point, I’ve been trying to get better at the fine art of making introductions. Every week I probably make a couple of introductions between people I think should know each-other. It’s a simple format:

Intro: Anne, meet Bob

Hi guys, I thought I’d make an introduction because (reason).

Anne, Bob is (reason for relevance) and (how I know him / he’s amazing).

Bob, Anne is (reason for relevance) and (how I know her / she’s ace).

I hope something good happens because of this intro! (Etc.)


Answer “But why?” with “I don’t know yet”

A couple of weeks ago I went to an art hack with the theme of making things out of data in a weekend. I made something called Cryptographics, that lets you encrypt text and represent it as a graphic that you can wear on a t-shirt, sew into a quilt, make into a print for your wall, and much more. A few people asked me “but why”? And I could flippantly reply “because art”, but more accurate would be to say “I don’t know yet”.

Undirected play and experimentation is something we tend to lose as we become adults. I’ve made my rule “create something every day”, and one of the side effects of that is that I’ve been doing lots of little experiments as a result. From each of them I end up having interesting conversations, and that’s possibly a way of rationalizing doing playful things. You get to meet people, and in my opinion, the best networking is done whilst talking about things other than work.

Goldilocks serendipity

There is an obvious danger that you can get distracted from your work by trying too hard to do open-ended things that don’t have an immediate benefit. But also, if you have too little opportunity for serendipity — that zemblanitous state—then you’ll end up stuck in a rut. The answer, is of course, to find a goldilocks zone where it’s not too much and not too little.

These are all just examples of things I’ve been doing around being sagacious. The big thing for me has been in considering serendipity in making decisions about things, I’m trying to make it so that as we build Makeshift, we’re enabling happy accidents to occur for us and for those around us. You might want to try adding a little bumping-into-ness to your work life too.

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