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Three Proven Ways to Create Your Own Serendipity

According to the internet, we have Horace Walpole to thank for the addition of the word “serendipity” to the English lexicon. He first used the word in a letter to Horace Mann penned on January 28, 1754, noting that he derived the term from a “silly fairy tale.” Said fairytale centered around three Persian princes who sailed off to an island called Serendip in pursuit of riches and made a series of fascinating and unexpected discoveries on their journey. Today, we know Serendip as the island of Sri Lanka, and many use the word serendipity to refer to delightful encounters that come about through happenstance.

With time, some have come to conflate serendipity with luck, which I think is a mistake. Where luck must rely on some mystical power from a source over which we have no control, the power to create the conditions for serendipity is within our own hands. Entrepreneurs, especially, should master the art of creating serendipity. Each day we have the opportunity for enriching, delightful encounters that we couldn’t have planned. These interactions are often what spark our creativity and challenge our thinking in ways that open new possibilities for our businessess. We'll miss out, though, if we're not intentional.

Here are three ways to create your own serendipity, and they're all FREE:

1. Smile at strangers.

I say this with a few caveats, recognizing that we do live in a scary world where not everyone will wish us well. Still, we must do unexpected things to have unexpected results. Maybe we’ve gotten into the habit of looking unapproachable because we want to block any unwanted or unwelcome attention. Trust me, I’m with you. I can mean mug with the best of them. It’s possible, though, that by looking unapproachable, we’re also shutting down conversation from polite strangers, who could be potential clients or collaborators. Be reasonable and use discernment and consider if you could be more approachable by simply smiling and greeting others as you move through the day in safe spaces.

Here’s a quick related story: Recently, I took an Amtrak train from Washington D.C. to New York City. It was a 5 am train; and I’m not what one would consider a morning person. While waiting for the cafe to open, a stranger sat across from me. We smiled and greeted each other. It turned out that we were both entrepreneurs. He had extensive experience and was incredibly generous, even offering me an impromptu coaching session during our train ride. We’ve since connected on LinkedIn and stayed in touch. I’ll never quite know what prompted that random act of generosity. Our paths may cross again in an intentional way or they may not. Still, I’m grateful our serendipitous meeting.

2. Go outside.

There’s a Ghanian proverb that loosely states, “You must get out of your house to learn.” I constantly find new ways in which this proverb is instructive. Our “house” may be the physical space in which we’re working each day-- especially for solopreneurs and freelancers. But our “house” may also be the figurative space that we occupy mentally and emotionally that can become cramped and so introspective as to be insular and unproductive. We must get out of our house daily to keep learning, growing and advancing, not just in business, but as people. Our “house” may also be our worldview, informed by our cultural and social networks. We must get out of our house, going beyond what’s comfortable and easy to forge new connections, to uproot closely held, unhealthy biases. We must get into the habit of periodically going outside our daily routines, putting ourselves in spaces that provoke, inspire and educate.

What this could look like: Schedule visits to a local museum, theater performance or cultural activity where you know you’re likely to encounter folks of a different background. Start learning a new language, maybe using a free language app. Take a 15-minute walk each day around your own neighborhood, being mindful to smile and greet at least one neighbor. Join a diverse community where you’ll have close proximity to people from various professional backgrounds. When I found that my professional network, though full of amazing women, was becoming very homogenous, I sought out diverse communities of women leaders. I joined Tide Risers and Ellevate Network. I’ve found both organizations incredibly valuable in helping me get out of my house.

3. Mentor someone.

We’ve heard it said that “time is money.” That’s what makes giving of our time such an incredible act of generosity. Like money, time when invested well, can lead to rich rewards in the future. While it may seem daunting, it doesn't take much time or commitment to mentor others. For some, a fifteen minute conversation, an email exchange or just a quick text checking on them or sharing a helpful resource would go a long way. Generosity begets generosity. If you want a sure way to have more unexpected, delightful encounters in your life, then give generously of your time and knowledge to others. You’ll be amazed at how quickly good things come back to you.

Here’s a real life experience: Last year, LinkedIn added a feature that allows members to offer career advice to other members. I’ve been doing this for several months, and I’ve met amazing people. Not surprisingly, the most serendipitous things have happened as a result. Just last week, I hired one of the young women who reached out to me for advice to provide freelance video production support for an upcoming event.

Let's say it again for the people in the back.

There’s so much we can’t control in life, so embrace the things we can control. We can smile and greet people throughout the day, if we choose to. We can go outside, opening ourselves up to new experiences, if we choose to. We can mentor someone else, sharing what we’ve learned generously, if we choose to. It's our choice. Serendipity awaits.

Danielle Kristine Toussaint, founder + CEO of She Thinks Purple, is a storyteller, strategist and social impact leader. She has been the writing pen behind op-eds and speeches for Huffington Post,, and TEDx. Danielle holds a B.A. in Political Science and African American Studies from Yale University and a M.S.Ed from the University of Pennsylvania Graduate School of Education. She’s a founding member of Tide Risers and excited to expand the network to Washington, D.C. in 2019. She is a member of #BFFLabs: Black Female Founders Pre-Accelerator Spring 2018 Cohort.


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