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Nicole Stiffle

Artist & Community Builder

San Francisco, CA

While it meant navigating uncertain waters and overcoming setbacks and challenges, leaning in to pursue my happiness and my dreams allowed me to redraw the borders of my success.

When I was a little girl, I would sometimes ask my mom to draw a picture of my future: Who will I be? What will my daughter be like? Who will be the man I fall in love with? A woman of great inner strength and conviction, my mom would answer the same way every time: Act as if you’re not going to find anyone, and figure out how to make yourself happy. Raised as the only girl among four boys (who all admit she is the sharpest wit in the family), my mom broke convention in many ways, not the least of which was asking my father for his hand in marriage. My mom’s point was not that I would never get married – it was that the most important thing I could do for myself (and for my future partner and family) was realize that no one else could be the source of my happiness.

Growing up, my dad imparted slightly different wisdom. He had become a lawyer by no active desire of his own. In his modest Jewish upbringing, the choice was simple: be a doctor or a lawyer, so you can provide for your family. Despite not doing so himself, my dad encouraged me to pursue my passions. He made me believe I could accomplish whatever I set my heart and my mind to achieve. When I demonstrated artistic ability, he encouraged me to pursue a path less “practical” than his own, and repeated a phrase that became my mantra: But can they draw? Saying this was his way of giving me a well of confidence to draw from. He made me believe that despite the setbacks and challenges I faced, I had a unique talent that gave me license to go after my dreams.

Following both pieces of advice, I set out on an artistic path that led me to exhibit my work in galleries (and by luck, one museum) and work at the Whitney in New York. One day, I found myself standing rapt with attention as a previously unknown artist, who had been catapulted into momentary fame, talked about a piece that had been selected for that year’s Biennial. In that moment, as I imagined my own work on the wall one day, I remembered an old professor’s description of the arbitrary, difficult path to success as an artist: “Take a look at the list of artists from the 2004, 2002, 2000 Biennials. See which ones you recognize. Some perhaps, but most you won’t.” What he meant was that even if you “made it” by getting into one of the most important shows in the art world, it was no guarantee of continued success. I knew I wanted to pursue big dreams, but I wouldn’t be happy if my life was defined by the chance, subjectivity and financial uncertainty of an artistic career. I decided to take more control of my destiny.

Even though I had not taken a single math class since high school, I leaned in and spent hours studying for the GMAT. When I got an interview for my dream school, I leaned in, bought my first suit, and (tags still on) danced in the bathroom before the interview to quiet my nerves. After spending my life defining myself as an artist, all of my leaning in had landed me in business school, a fish out of water, in a sea of bankers and consultants.

I had never so much as opened an economics, finance or accounting text, yet suddenly I found myself taking classes in all three with people who had focused their majors and careers on those subjects. I was regularly nauseous as I silently prayed I would not be cold called while my outwardly confident classmates’ hands shot up like lightning rods around me as they strung together answers that included phrases like “lever up”, “bootstrapping” and “latent demand” (sometimes all in one long, incomprehensible sentence… like this one!). I quietly listened to classmates scoff about “what a joke” the econ midterm was (the same test I was convinced I had failed). Rather than speak up to say it was not a joke to me, I attempted to hold a steady, convincing smile as I fought back tears.

In the most difficult moments when my confidence was deeply shaken, I gathered strength from the well of the wisdom I had inherited from my parents. On those lowest, exhausted days when I doubted myself, I straightened my backbone by remembering I had inherited my mom’s inner strength and conviction, and that I was in pursuit of my own ultimate happiness. As I struggled to stay afloat in classes that challenged me, I drew a quiet reserve of confidence by remembering my dad’s mantra: But can they draw?

While it meant navigating uncertain waters and overcoming setbacks and challenges, leaning in to pursue my happiness and my dreams allowed me to redraw the borders of my success.

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