Job seekers, entrepreneurs, and executives aiming to advance their careers face unprecedented uncertainty. To succeed, they must be ready for the unexpected and turn it into positive outcomes by seeing and connecting the dots. In short, they need to nurture serendipity: the unexpected good luck resulting from unplanned moments, in which proactive decisions lead to positive outcomes.
How can we cultivate this “smart luck”? By setting hooks and planting bombs. These two practices can help us flex our serendipity muscles at any time. Here’s how to deploy them.
Setting Hooks
Serendipity hooks help people get interested in you and help you learn what you’ll find intriguing about them. The process starts when you use memorable or engaging talking points, whether in the park or on Zoom. When Oli Barrett, a London-based entrepreneur, meets new people, he sets several hooks aimed at surfacing overlaps with the other person. If asked, “What do you do?” he will say something like, “I love connecting people, have been active in the education sector, and recently started thinking about philosophy, but what I really enjoy is playing the piano.” That reply includes four hooks: a passion (connecting people), a vocation (education), an interest (philosophy), and a hobby (playing the piano). If he merely responded, “I’m in education,” the potential for others to connect the dots would be quite small. But by setting several hooks, he increases the odds that the listener will respond with something like: “What a coincidence! I’m thinking about starting a company that is all about connecting people. Let’s talk!” Hooks allow others to find and latch onto something that relates to their lives or what they’re looking for, making serendipity more likely. Setting them is easier if we “have our story straight”: What are we passionate about, and what could we contribute that is relevant to the other person?
We can also give others the opportunity to set hooks. One way is to ask questions differently and be open to unexpected answers. Imagine being at a (virtual) conference and meeting a new person. You might go on autopilot and ask the dreaded “So, what do you do?” That tends to box your conversation partner into a corner. Instead, use broader openers, such as “What are you interested in at the moment?” or “What is your state of mind?” Such prompts may lead to serendipitous outcomes by allowing the other person to set one or more of their own hooks.
Hook-setting isn’t limited to private conversations. We can set hooks at events, even if we’re not the speaker — for example, by standing up during a Q&A and saying something like: “Thank you for the inspiring presentation. As someone who just went through [XYZ period] or who aspires to do [XYZ activity], I was struck by what you said about [XYZ topic]. What would you advise people like me to do?” This gives the entire audience insight into how you and your life and career might related to theirs. In my experience, in a group of a couple hundred people, usually several will respond to such hooks by seeking out the person who set them: “What a coincidence! I recently went through XYZ as well….”
Planting Bombs
Through technology and spatial design, it’s possible to create entire containers of potential opportunity — what Mattan Griffel, an entrepreneur and adjunct assistant professor at Columbia University, calls serendipity bombs — by connecting with groups of people.
One tactic is to write speculative emails to people you admire. I know executives who do this, and you’d be surprised at how often the recipients of those unsolicited correspondences write back because they see some unexpected mutual interests or reasons to engage. For example, an executive might have wanted to expand into exactly the area that a speculative email referred to. If you can’t find an email address, consider tweeting or using the InMail function on LinkedIn (which lets you send messages to people you don’t know). In many professional fields, academics are a good starting point for making connections. Their contact details tend to be on their university’s homepage, they usually know senior people in industry, and they are relatively open to making introductions. Even with all the background information available to us with just a few keystrokes, we can’t know everything about a person, so you’re creating new opportunities when you plant this type of bomb. It’s a low-risk strategy to expand your network and nurture the conditions for serendipity. Even if nothing comes of it immediately, you are on your correspondent’s radar (assuming they read their emails, that is!).
You can plant serendipity bombs within organizations, too. One traditional way is to invite someone in a different department or function to coffee or a video call. Leaders might pair people up randomly to get unexpected conversations started and, nowadays, to help overcome lockdown disconnection. Our research has shown that companies and incubators have developed a myriad of similar ways, such as conducting postmortems (incentivizing people to share ideas that did not work out, which might “serendipitously” work out in other contexts) and using flexible space design (for example, placing the mailboxes of diverse people next to one another so that those people will “bump into” one another), to increase serendipity, especially in the context of uncertainty.
Success Through Serendipity
Most top executives will admit that they’ve achieved their position through not just intelligence and hard work but also luck. Still, we can all do a better job of creating unexpected opportunities and connecting the dots with others so that they can help us or we can help them. With a serendipity mindset, every interaction might open a new path — for finding love, meeting an investor, making a friend, forging a new interest, or landing a new job.