Starting Up Your Passions: Finding a Career That Interests You
I loved my time at Hamilton. So much so that I was totally unprepared for the “Hamilton withdrawal” I felt the first 18 months after school … that first fall in particular. That sense of loss was sharpened by being completely miserable at work. I’d entered Hamilton with my sights on an English major. I quickly saw that most of the “ambitious guys in my circle” were aiming for finance jobs, and majored in economics to prepare them for those careers, so I did the same. The career center was very helpful in getting my resume and myself ready for finance interviews in New York. I ended up interning at Lehman Brothers the spring of my Sophomore year (via the New York City Program) and at Goldman Sachs the summer before senior year. Both were good experiences, but mostly I was proud of myself for getting those internships and confident that I was “on the right path.” In hindsight, I spent almost no time thinking about what careers best matched my personality and interests.
I took a job at a smaller firm after graduation and was almost immediately miserable (unmotivated, performing poorly, embarrassed by said performance). I didn’t have the maturity, or self-awareness, to understand that my job was the single biggest cause of that unhappiness (though missing my friends at Hamilton didn’t help any). Luckily I lost my job in the fall of 2008. The relief I felt walking out of the office that final time surprised me. I should have left long ago, but quitting a job seemed outside my control. Losing that job kicked off an exploratory phase that I’m incredibly thankful for. Almost immediately, I went to Ohio and spent the last two months before the ’08 election volunteering for the Obama campaign. From there, I went to Seoul, South Korea for 18 months of teaching and traveling. In 2010, I landed back home (Sonoma, Calif.) and accumulated three part-time jobs: pouring wine at a wine bar in San Francisco, communications at an NGO, and sales at a travel technology company (GoOverseas.com). It was so much fun to work three jobs at once, they were all so different.
That difference also made them easy to compare … it was evident I was learning the most and find the most fulfillment at Go Overseas. I went on to spend the next eight+ years there, eventually as the COO and co-founder. It was exhausting work but there is no better place to learn than a startup. Every day is different, constantly needing to throw yourself into challenges you have little knowledge of. Doing that repeatedly forces you to get good at problem-solving, adapting, and practicing the fundamentals of discovery and organization.
I left Go Overseas in the summer of 2019 and took six months off (I wish I’d taken longer but recognize I was incredibly privileged to take even that long). In December, I joined the team at User Interviews as our first director of customer success. I was charged with setting up the department, and while I had little experience with scaled customer success, building systems and running experiments was familiar territory. I’m now in the midst of taking over the management of our revenue org (sales + cs + account management). It’s been fun to have my job change as quickly as it has, and thrilling to be part of a fast-growing team. My clients are also some of the most talented researchers, product managers, and designers in the world. They’re an exacting bunch, but incredibly empathetic and consistently brilliant.
User Interviews has been a fully remote team for several years and required no workplace adaptations when the pandemic hit (though many coworkers found partners and children now working from home, too). The company has continued to grow, as companies around the world research how their customers are reacting to, and being affected by, our new world. I spend my days supporting and strategizing with clients continuing to build customer-facing systems that maximize revenue, provide joy, and do both as efficiently as possible.