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Powering a Culture of Serendipity

One of the things I miss most since our lives changed with the pandemic is “discovery”: those “random” encounters and moments of serendipity (which, as it turns out, are not so random after all) that were connected to travel, exploring and working from different places, attending events and bumping into people on the street.

Working from a cafe and hearing a stranger at the table next to you talking about something you’re currently reading, and opening up the conversation only to find out you both used to live in the same area of a different city. Or having the colleague sitting next to you show you what they did at the weekend, which suddenly sparks an idea in your head that you integrate into your next project…
Or meeting someone at an event, finding out you’re both working in the same field, and learning that the other person is actually looking for a collaborator or support on a project…

It’s those small moments that make everyday life so exciting and enriching.

You might think those moments just happen by chance and are “luck” — but without realizing it, we actually have the active power to shape our smart luck, even in times of social distancing and working apart.

We can actively empower a culture of serendipity and set ourselves up for moments of serendipity to happen.

In his book The Serendipity Mindset, Christian Busch writes “Developing a serendipity mindset helps us see triggers, connect the dots and develop the tenacity necessary to focus on and influence valuable outcomes.” It’s about looking at the world with open eyes and connecting the dots.

Mystery, wonder, surprise are the emotions most undermined by our always-on connected 24/7 digital culture. If we are absorbed by our work and the daily grind, we avoid creating moments of serendipity and space for new ideas. And in a world where we often can’t predict what will happen tomorrow, the best we can do is to embrace our environment (personal and workplace) and actively set ourselves up for moments of serendipity.

What we can do is develop a serendipity field — by influencing different enablers, such as communities and companies; removing the barriers to serendipity in our own thinking, lives and workplaces (e.g. senseless meetings, email overload); and having our eyes open to seeing triggers and all the dots that could be connected.
We can’t choose where and when those moments happen, but we can choose to create space for them and nurture serendipity by learning the progress of spotting those moments and connecting the dots.

In our OOO Hours this month with Michelle Morrison, Design Program Manager at Dropbox, we explored how we can design a working culture that powers serendipity.

As we’re navigating our way back to work, we’ve summed up some of the insights from our session as well as resources and small, immediate adjustments that will hopefully make a difference in your day-to-day experience:

Ways to Power Serendipity

Design a working culture that powers serendipity.

Create space to connect on shared values
Create room for people to find out what other people care about and what’s on their minds. Do they have similar passions or hobbies, a side-hustle or love for animals? Getting to know people better will make it easier for you to connect the dots whenever an opportunity comes up.

Create moments of delight and joy

Little moments and acts of care can make a big difference in relationships and spark new conversations. Why not sending a thank-you card to someone for helping you out? This might result in new conversations and will build trust and feelings of connectedness, which are some of the basic components that make serendipity more likely to happen.

Change the format
Do things differently. Try to call people rather than texting them, or do whatever you feel could get you out of your comfort zone.

Find out what people need in order to work with you (our friends at Dropbox actually created a handy template for this). Try work sessions and open brainstorms on a shared doc or through other tools (e.g. mind mapping in Mural, brainstorming in Miro) to recreate the “in the room” moment in a digital space.

Start meaningful conversation
When attending an event or meeting new people (virtually or in real-life), don’t just ask people to introduce themselves by what they do. Use variations such as “What’s on your mind right now?” or “What are you currently most excited about?” or “What are you currently exploring?”.

These changes might be small, but they can have a powerful effect on our everyday lives. Even in our changing world, moments of serendipity can still happen — if only we open ourselves to letting them in.

Thank you for reading! This article was originally published in my newsletter
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If you have any questions, comments or would like to get in touch, please reach out to: hello@alicekatter.com




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Alice Katter

Alice Katter

Curious optimist currently designing culture and community programs + tools at Dropbox. Writing about community, future of work and out of office culture.

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