The Serendipity Mindset
I was just running the numbers, (you know, as you do) and it turns out that this week marks my thirtieth move since kicking off this unpredictably itinerant life at the age of 17. I just turned 43 this weekend, so that averages out to packing and unpacking nearly once a year for the past 26 years. With every move, the quips are the same: I can’t keep up with you! How do you do it?, or, This’ll be the last time, right?, which at this point is basically a running gag with my parents, and to some extent, myself.
There’s a line from a song by The National that I think about a lot, for various reasons, when I’m in various moods:
How can anybody know/How they got to be this way.
It’s a good question. Of course I recognize the cascading effects of my choices and decisions, one thing leading to another, whether by volition or chance. Nevertheless I sometimes wonder if I’m on a kind of vision quest, or if I'm just irrepressibly restless, the kind of gal who likes to roam around? Honestly, I’m not sure.
I’ve never been someone who's had a straightforward answer for where I see myself in five years, or a crystal-clear picture of an imagined future. That’s not to say I’m without goals or aspirations; it’s rather that I prefer them to be a bit wooly and imprecise, more sentimental than tangible in nature.
Considering my hopscotch moves between cities and careers, a lightbulb went off for me reading about what researcher Christian Busch calls the “Serendipity Mindset.” “Serendipity is smart, active luck,” he says. “It’s when you see something in the unexpected and connect the dots.” If you know me well, you know that I’ve been plugged into this way of thinking for years, well before I (only somewhat regrettably) tattooed the word inside my left wrist. This mindset is perhaps why I’ve always been drawn to the principles of design thinking, both inside and outside of my work in design.
In his infinitely inspiring book Creative Confidence, IDEO co-founder David Kelley writes that “design thinking relies on the natural–and coachable–human ability to be intuitive, to recognize patterns, and to construct ideas that are emotionally meaningful as well as functional.” He goes on to suggest that you can “get good at being lucky,” meaning that serendipity can be cultivated if you allow yourself the freedom to pursue what you’re curious about, letting your mind, and maybe even yourself, wander. This might seem like a slippery slope towards dilettantism if the broader aim wasn’t to synthesize ideas and insights into knowledge you can apply on a practical level.
At least that's what I have to remind myself when I worry about whether I’ve lost the plot, or worse, that I won’t be taken seriously. How many pivots, in how many directions before–to paraphrase more ponderous lyrics–I can’t move forward because I don’t know which way I’m facing. At what point do bold pursuits and whimsical-seeming moves between cities and jobs and ideas just become erratic and irresponsible?
Self-awareness isn’t merely a way to shrug off accountability for making mistakes and miscalculations (I’m looking at you, failed bagel business partnership), but a serendipity mindset shouldn’t be written off as indulgent capriciousness, either. Whether by choice or by circumstance, a linear narrative never felt accessible or appealing to me, GenX hanger-on-er that I am. We may have been taught to value security and stability, but more often than not, the world has laughed in our face: HAHAHA you want to buy a house/save for retirement/have a fulfilling career/AND eat avocados HAHAHA!
In my lifetime–to say nothing of all those poor Millennials and GenZ’ers behind me–uncertainty has been the norm. The way I see it, being able to change one's mind, to switch gears and change course is less of a privilege and more of a survival skill. Cultivating serendipity isn’t about chance or luck or risk-taking; it’s about seeing the world with your eyes wide open, and always being on the lookout for the next place to leap. Because you never know when you may have to jam.