Don’t Just Embrace Serendipity in Your Career — Engineer It

6 min readJan 15, 2021

Serendipity may play a bigger role in our professional lives than we realize or care to admit. But by recognizing that truth and creating opportunities for lightning to strike, we open ourselves to new possibilities.

Photo by Cynthia Magana on Unsplash

For those focused on building businesses, crossing things off to-do lists, or crafting life plans, counting on luck or serendipity might seem frivolous or even outright silly. Surely, making big moves and getting things done does not leave time to wait around for luck.

Many people probably consider luck and serendipity similar concepts, even to the point of being synonyms. In fact, I bet you didn’t bat an eye when I used them as such in the paragraph above. I want to suggest here, however, that they are dramatically different in their impact on our established mental models of the world.

Serendipity happens when you are looking for something but find something else — something better — entirely.

Look back on big moments in your life, and you will likely realize serendipity plays more of a role than you might think.

What if, instead of lamenting them, we viewed accidents as playing an essential role in our everyday lives? What if unanticipated events naturally give way to discoveries? Could we cultivate a way to expect the unexpected and to find the unfound? How would our lives look if we became more open to serendipity?

Perhaps most importantly, can we engineer serendipity?

Entrepreneur Lane Becker is a thought leader studying the role serendipity plays in our lives. Along with one of his startup co-founders, Thor Muller, Becker wrote Get Lucky: How to Put Planned Serendipity to Work. He calls the book a manual for serendipity in the digital age. As the pace of change increases and the amount of information at our fingertips grows exponentially, the authors make the case that we all need to embrace serendipity to succeed. Becker and Muller say that we shouldn’t think of serendipity as an isolated event that happens spontaneously, but rather as a mindset to cultivate. We can strive to become better and better at letting serendipity bloom in our lives.

“If luck is a tricky thing to talk about, serendipity is even trickier,” Becker said in a 2012 TEDx talk. “It usually just ends up in self-help manuals. I am here to reclaim the term. I talk about serendipity as a very specific subspecies of luck. It is the kind of luck we have agency in. It is the kind of luck that our actions can affect.”

Becker and Muller say that if you’re trying to embrace serendipity, routine can really get in the way. During the early days of the pandemic, many of us put effort into creating a routine to add structure to our new normal. After our usual day-to-day patterns were upended by lockdowns, social distancing and travel restrictions, we’ve come to see just how valuable having a stable routine can be for our mental health. At the same time, doing the same thing, seeing the same people, experiencing the same environment without change — this is no recipe for accidentally encountering something new and important.

If the business world wants to treasure serendipity, what do we do now that in-person conferences, tech meet-ups, and networking breakfasts have all but disappeared? How can professional serendipity be engineered the way it once was in those spaces?

MORE FROM OUR EXPERT CONTRIBUTORSTo Stop Future Hacks, Look to the Past


Before the global pandemic, your professional networking may have looked like a calendar filled with in-person events like conferences, happy hour gatherings, meet-ups, or workshops. Below are ideas for how we can we work within our new normal to continue to engineer serendipity.


What if you hosted an event people couldn’t stop talking about? Ask three of the most connected people you know if they would be up for attending a 60-minute virtual gathering you organize. The catch? Each of them must also invite one of their connections. You’ll end up with seven people in a virtual space who have all agreed to an hour of fostering new connections. Don’t forget to have a clear topic for the gathering so all attendees come in knowing there’s a clear purpose. Having a clear intention at the start of the gathering also increases the chances that attendees walk away from the event feeling like it was unique and unforgettable. An example topic could be “Highlight and Lowlight,” an activity in which everyone on the call is given three minutes to share a highlight of the year and a lowlight of the year with the group. Then, the group is given five minutes to provide feedback and thoughts on what they just heard.


Make a list of five contacts that you have fallen out of touch with. One way to help jog your memory about these once meaningful connections is to look at your 2019 calendar. Did you attend any conferences? Did you meet anyone interesting there that you haven’t talked to in a while? How about the organizer of a meet-up you used to attend before the pandemic? Have you checked in on them to see how things are going in their life? Catching up with someone you don’t know well can be just as fruitful in the serendipity sense as meeting a new connection.


Do you know someone who organized amazing events pre-pandemic? Or did you experience their work as an attendee but never connected with them post-event? Now is the time to support talented event organizers who could use a hand in continuing their work in what may be a totally new way! Reach out to an event organizer you admire — even if you have never met them before — to see what they are working on in their community during the pandemic and offer your help as a volunteer. Volunteering to help plan an unforgettable event is just as valuable as organizing one yourself.


Lunchclub is a startup that makes professional introductions to new connections for its users. These one-to-one professional connections happen over video. It may just be the future of professional networking in the age of COVID-19 and even beyond the pandemic.

Lunchclub is on a mission to power a future of work in which making new connections is easy, meaningful and fun. The company is backed by Lightspeed, Coatue, and a16z. Users tell Lunchclub about their background, goals, and interests. Each week, they opt-in via email reply if they would like to make a new connection. From there, Lunchclub’s AI matches users for a one-to-one video meeting.

CEO and co-founder Vladimir Novakovskiknew thinks a lot about how people connect and how meeting the right person could change your life. What started as experimenting with products that reminded people to reach out to their existing contacts who had turned into cold contacts over time morphed into something different. Users sign up and indicate their city, goals, areas of expertise, and interests. They then opt-in for meetings on a weekly basis, with the option to skip a week if life gets busy or to add extra meetings on a week where they would like to meet more new connections. From there, Lunchclub’s machine learning algorithms help users network from home either locally or globally by connecting them to new people. Turns out, a worldwide pandemic has led to an increased number of sign-ups for those seeking curated one-on-one professional connections.

Professional serendipity doesn’t have to be something that we only associate with traditional, in-person networking events. Exploring our social distanced, locked down landscape with curiosity can lead us to connect with interesting people through new channels — and learn, discover, and grow along the way.

This article originally appeared on November 10, 2020 here:




Jacqueline Jensen is a COO, former venture-backed startup founder, TEDx speaker, author, and Royal Society of Arts Fellow.