Engineering serendipity in the Digital Age

Why is it that the events that matter most are often the ones we can least predict? You take a trial yoga class that inspires you to quit your job and travel. You get a new job after a random chat with someone you meet at an airport cafe who refers you to a company you’d never heard of before. You come up with a product feature that occurs to you while you’re taking a shower which then goes on to revolutionize your product’s business model. So, what’s the deal?

We’re often taught to believe that opportunities come through very specific ways. To get a job, you either apply for jobs through websites or use your network. Or, to Why? Because, we are psychologically wired to stick to things that match our expectations and discount those that don’t. There’s nothing wrong with this per-se but it’s rather tunnel-visioned. This brings us to the importance of being aware of serendipity.

Serendipity is the ability to take a chance occurrence — a surprising idea, person or event — and make creative use of it. Yet, it’s something that can be rather complicated to pull off in the midst of our busy work lives. Here are a few digital serendipity hacks I’ve used to land my first job along with a number of hackathons around the world. Use them, abuse them, or be amused by them.

Set Google Alerts

When I was hunting for my first job, I knew two things. I knew I wanted to work for an internet start-up and that I wanted to be in Southeast Asia. But, I found it overwhelming to keep a tab on all the different startups gaining traction and funding. The conventional approach would have been to scour through all the startup websites that exist (which I also did) but I felt it would be a lot more efficient if I received a daily email digest that had exactly what I wanted to see in a condensed form. Each day, I monitored the results closely. This fixed the information seeking part of the problem.

With the time I saved using my hack, I instead spent effort on
dreaming up product ideas for companies based on the maturity, target problem and funding/expansion stage of the companies I discovered using my hack.

Now, how do you apply this?

In the search query, enter the topic you want to be informed about. I usually add certain terms in double quotations just so I get results that are specific in some form or the other. For instance, if I’m keen on knowing what’s brewing in the travel space in Southeast Asia- I would monitor “travel” funding Southeast. As soon as you type a topic, you’ll start getting results that would be similar to what you’d receive in your inbox. Keep tweaking it till you start seeing relevant results. And, once you’ve done that, you’re pretty much sorted.

Become an Idea Machine

Almost always, great ideas and happy accidents don’t emerge from a single source or entity, but at the intersection of a range of media and people.

There was this phase in my life when I was absolutely obsessed with James Altucher. As a hedge fund manager, founder of over 20 companies, and author of 18 books, he has made and lost millions of dollars over the years but he’s never been one to shy away from the ugly side of failure or hide the fact that he doesn’t have all the answers. I’d read all his books, listen to all his podcasts, and follow every piece of advice he spewed out. One of his most popular books, Become An Idea Machine: Because Ideas Are The Currency Of The 21st Century, revolves around a simple principle: Write down 10 ideas every morning. Initially, I was rather skeptical about this. Ideas are a dime a dozen- it’s the execution that ultimately matters. But, along the way, I realized that writing these ideas forced me to flex my idea muscle, think of creative solutions to problems I was perhaps facing at work, and also pushed me to initiate projects and reach out to people I’d have never reached out to normally. I carry my ideas book with me everywhere — a number of the ideas I’ve acted on have come to me in my daily bus commute to work or during meals I’ve shared with friends.

Here’s a page from my Ideas book.

Keep Calm and Scour On

Another hack that’s massively helped me is using articles/news/blogs as a breeding ground for ideas. Let’s take this article for example: (Link here:

Below are two snippets from the article:

Less than a week after acquiring Ticketfly from Pandora for $200 million, today Eventbrite has announced another deal to mark its deeper move into music events: the company will now show information about concerts and music festivals Spotify. Specifically, it will recommend Eventbrite-powered events relevant to the music people are listening to on the streaming music service and their overall music preferences.

Ideas that come out of this for me:

  • Spotify ad alerts on concerts happening around me (possibly recommended to me based on my listening history)
  • Eventbrite pages that have a Spotify playlist linked to the artist(s) so that if it’s an artist I’m not entirely familiar with, I can listen to his or her songs before I purchase tickets.
For now you will not purchase on Spotify’s site, but on Eventbrite’s “in two quick taps,” similar to how you purchase tickets there on the back of other distribution partnerships that Eventbrite has with Facebook, Bandsintown, Discotech, and Songkick.
  • Using video ads as a way for listeners to purchase tickets or find out where the artist is going to be performing in the near future.

I’d then take these ideas and craft them into a suggestions pitch/article! Once the article is ready, it’s all about marketing it to the right people.

A lot of what has happened to me in the recent past has been the result of making creative use of a surprising idea, person or event. When you speak to the same people and do the same things as all those around you, you end up travelling in a straight line along with everyone else. Parallel lines never cross- serendipity requires diversity. Try to design serendipity into your life because you’ll never know when it hits you and where it can take you.