Connecting the Dots

In line with my new book Connect the Dots: The Art & Science of Creating Good Luck (extended international paperback version of The Serendipity Mindset ), I’m starting a LinkedIn newsletter. It’ll focus on the question of how we can turn unpredictability into opportunity, and cultivate serendipity and “smart luck” in our lives.?

Here are 5 tips of how we can create "smart luck" and cultivate serendipity in our lives:

1) Set serendipity hooks : Whenever you communicate with someone, cast a few hooks – concrete examples of your current interests – thus maximizing the chance you and the other person ("coincidentally") latch onto common ground and shared passions, triggering serendipity.

2) Create potentiality: If you feel unfulfilled in your current job, jot down your key interests and offer your support to organizations or individuals in that space, be it as an assistant, freelancer, consultant, board member or whatever. You will start "bumping into people," and begin connecting the dots to create new opportunities. Instead of only asking yourself, "What is my potential risk of doing this?", ask instead, "What might I potentially lose if I don’t do this? Will I regret it?" Serendipity is about potentiality.

3) Accept imperfection: Accepting imperfection as part of life allows us to more easily reframe situations so that where others might see a problem (say, unexpected budget constraints), you see an opportunity (making the best out of whatever resources are at hand ), thus allowing more creative outcomes to emerge. That’s also where rituals such as “post mortems” or “project funerals” come in, where people openly and frequently talk about ideas that did not work out. Importantly, this is not about celebrating failure – it’s about celebrating the learning that comes from unexpected places. Oftentimes, serendipity happens when people “coincidentally” realize that an idea that didn’t work in one context, might work in another.

4) Start asking questions differently: Imagine you are at a (virtual) conference, and meet a new person. Many of us might go on auto-pilot and ask the dreaded “So what do you do?” This tends to put the other person into a box that is hard to get out of. Positioning ourselves for smart luck means asking more open-ended questions like “What did you find most interesting about…?”; “What brings you here?”; or “What project are you most excited about at the moment?” Such questions open up conversations that might lead to intriguing – and often serendipitous – outcomes.

5) Plant serendipity seeds: Take steps to use technology to your advantage in order to expand your opportunities. This may mean writing speculative emails to people you admire, or inviting someone in a different department or function to coffee or a video call. You can “plant serendipity seeds,” with the end goal being to engage in unexpected conversations that subsequently increase the chances you can connect the dots to an exciting opportunity.

Thank you for reading this first edition of the newsletter! If you’d like to be kept in the loop, please sign up. (More of this content can also be found in the international paperback Connect the Dots, which is now available in the UK and the rest of the world , and the hardcover The Serendipity Mindset is available here .)