A couple years ago, I completed an immersive, weeklong executive program in social entrepreneurship at Stanford’s Graduate School of Business. It was heaven: rooms full of smart, passionate “impact” entrepreneurs from across the globe; hours of stimulating lecture and debate with some of the most renowned business faculty in the world; late nights of socializing and homework (yes, homework!)–and all against the serene backdrop of 70-degree, palm-tree-lined Palo Alto, CA.
During one of the session’s icebreakers, we were paired off and then asked to introduce one another to the group — a clever way to ensure people actually got to know one another.
My companion had this to say:
“This is Jen; she’s an entrepreneur working to build the financial health of low-income teens through technology.”
I writhed against the “entrepreneur” label — it felt inaccurate, unearned: I was, after all, representing a non-profit I’d not founded myself. Though I was the third full-time employee and was playing an influential role in the strategy and operations of the nascent organization as its Chief Innovation Officer, I felt an uncomfortable turn in my stomach: I felt like a fraud, like it was going to be “found out” that I was not actually the CEO and founder of the company, and that my introduction would be discredited. “Oh, she’s just an employee there,” they might say. “What’s she doing here? I thought this was only for founders,” another might have prodded.
During that same session, the professor introduced himself by sharing some of the highlights from his dynamic, prolifically productive career. He concluded with this: “I know, I know — a lot of crazy left hand turns and right hand turns, right? But most successful people travel squiggly paths to success. They take risks. They follow their instincts. They try new things, fail, and try other new things. The point is that it’s your job to build the narrative around them.”
I have so much to say about these couple of minutes in that state-of-the-art classroom in tranquil Palo Alto, and the following email from one of you smart Magpies led me to plumb them the other day:
“Your recent post about the complexity of the words we choose (when you were describing your area of study) was great…yes, it is appropriate to choose your language based on your audience, but I typically don’t think there is a need to “dumb it down”. I don’t even do that for my young kids: I actually try to use more complex language and words with them, as I want them to hear it, question it, and learn it. I want to do the same, and do all that I can to be around people more intelligent than me, professionally and personally: I want to learn all about what they are doing and absorb all they have to offer. Those who do not want to learn from others – e.g. about an area of study of which they were not previously aware – make that decision to their own detriment. I got great advice from a colleague once: you never want to be the smartest one in the room.”
You never want to be the smartest one in the room. The words lingered over my head like a thought bubble in a cartoon for the next couple of hours. I realized that I rarely feel myself to be the smartest person in the room. This is not practiced humility, either: I know myself to be intelligent — but, in the past many years, I have pole-vaulted from one uncomfortable experience to the next, always nudging myself out of my comfort zone, routinely finding myself in rooms with people who are far more literate and skilled and sophisticated with the topic at hand than I. In graduate school, I cowed at the intellectual prowess of the faculty in front of me, and at the bold and well-read observations of my classmates. In my tenure as an executive at two different non-profits, I fidgeted and tripped over myself when pitching our concepts to well-established funders and partners in the space. At Stanford, I bumbled through my introductions to the rest of the serious, ambitious social entrepreneurs around me. When presenting the tech business I built with Mr. Magpie, I flustered inwardly — I had finally learned how to keep a game face, though there were occasional gaffes — while in the presence of slick investors, one of whom stood up in the middle of my empassioned pitch to stretch and throw his apple core into the wastebasket, pausing to linger idly at the window.
I am a perennial fish out of water.
In the aftermath of closing our business, Mr. Magpie and I often talked about the fact that both of us are generalists. We wondered whether things would have been different if either or both of us were specialists, say–one of us a developer and the other a career HR executive. Would we have elicited more trust from investors? Would we have known more about the landscape and been able to more easily sell our software? Would we have been able to build our minimum viable product more quickly, more leanly? I remember telling Mr. Magpie that sometimes I envied my friends who had picked a path in high school or college and pursued it with focus, thinking of the lawyers, the financial analysts, the doctors in my network. Not only were their career ambitions much clearer to them, but they had the comfort of expertise, the earned peace and confidence of knowing that they knew something more intimately and with greater sophistication than the vast majority of the universe.
Such musings are futile and possibly injurious intellectual exercises, as they’re willfully ignorant of the truth–which is that both of us are generalists. Smart, thoughtful, and ambitious generalists — but generalists all the same. Mr. Magpie quipped: “We’re Jack and Jill of all trades, but masters of none.”
Or is it that I’ve made a career out of being a student? That I am somehow, despite my better senses and occasional envy of others, drawn to the position of the novitiate? Maybe I’ve not afforded myself an opportunity to become a master of any one thing; I’m too busy moving onto the next.
Putting a more positive spin on things: am I, to parrot the formulation of that Stanford professor, a successful-person-in-the-making, twenty-two turns into my squiggly path, but not yet able to tell my narrative in a cogent and evocative way?
But success narrative be-damned, the truth is this: there’s been a sort of over-romanticization of failure, at least in the start-up space. I used to sing its gospel, too: “Oh, everyone fails — the secret is how quickly you can pivot” and “It’s not failing; it’s learning” and “Don’t think about it as success or failure; think about it as experiments.” I actually once gave a public talk to two hundred people at a design conference on this exact topic, and I started with this: It took Thomas Edison 10,000 different attempts at combining gas and filament to successfully create the lightbulb. Would we characterize those attempts as failures? Or necessary permutations and experiments that led him to the right answer?
But herein lies the problem: the old failure narrative only works when you wind up successful at the end. No one wants to hear about a pet food subscription service that lasted three years before its founders gave up and crawled back to their jobs in finance. And when you’re in the throes of closing down a business, there is absolutely no romance about it: it is heart-breaking, soul-crushing stuff, and I don’t wish it on my worst enemy.
In short, I find it difficult to characterize the kind of career I’ve had to date. I’m too much of a realist to call it a squiggly path to success — but I’m also proud of my varied accomplishments, even if they don’t all “hang together” in a straight-forward way. And regardless of whether my jagged career decision-making is owing to some underlying personal preference for risk, or the serendipities and bermuda triangles of life, one constant has been this: I have rarely been the smartest person in the room, and I much smarter for it.
Is it very embarrassing to admit that I am dying to try this broom? It has a foam end that picks up hair and dust and then you just wipe it off with a damp paper towel — seems like a much better solution than picking it out of the bristles of my usual broom. #Housewifeproblems