Nothing confused me more than trying to “pick” a career.
All my life, the world had presented me choices with no more than 3–5 options at a time (soccer/softball/swimming? Choir/videography/graphic design?) And I was happy to lilt down the path lit by the brightest teacher.
In high school, that was my film teacher, Jay Doublestein. His excellence in teaching led me to seek a film school for college and plan a career as Director of Photography.
🎓 🔜 🎥
Once I got to that film school, however, I found the degree was cost-prohibitive for me — I couldn’t afford to buy the 8mm film and pay the development costs I would have over the next 4 years.
But I had new favorite teacher—Nisha Shanghavi, professor of art history—and I was off to the races.
In the contained space of a college, the local maxima are readily apparent: start a student club, run another, take the best classes, get straight As, work for the school, and meet everyone you can. And that’s more or less what I did.
After undergrad, you obviously go on to get more degrees. I mean, what else was I going to do with a B.F.A. in medieval Art History and carpetbag full of extracurriculars?
But despite my best efforts—and a Latin immersion program to boot!—all the PhD programs rejected me.
“Get a Masters degree and try again,” they all told me. But (again) I couldn’t afford it.
Nobody pays you for a Masters degree. You have to buy it, and the cheapest ones sit pretty at $30k minimum.
Then my crisis began. What was I doing anyway? What was I good at? What did I like?
Everyone said “follow your passion” but I didn’t have one.
Don’t get me wrong, I’m passionate about everything, but I didn’t have any one thing that motivated me. The world was limitless, and I didn’t know where to start. That unknown was completely debilitating. Terror ruled my life for a while.
Without anything else to do, I moved to NYC after graduation and lived with the generous family of a loving boyfriend. I moved in with $342 in my bank account.
“I have a degree in art history,” I rationalized, “New York City is basically the capital of the art world. Let’s see what I can do there.”
In the first two months I applied to 132 jobs. Only 3 ever called me back. Two were for nanny gigs, one was a gallery management position I really had no business applying to at all.
There’s a pretty codified path through the art market:
- Sophomore summer: unpaid internship
- Junior summer: unpaid internship (at a nicer gallery)
- Senior summer: paid internship! 💸💸💸
- Graduate and work from gallery assistant…
- To associate…
- To the director path for sales and curation or…
- To manager for operations and staffing.
The job was way out of my league, but I applied anyway. I was applying for everything.
Miraculously, they needed someone with my skills and temperament more than someone with a bunch of relevant experience.
I got the job.
🖼 👭 🖼 💸 🖼 👫 🖼
Fast forward 3 years and you’d see me still at the gallery, but getting antsy. The learning curve was pretty steep at the beginning, but after getting a handle on things, that curve had started to taper off and I was thirsty for new challenges.
I got coffee with every friend-of-a-friend-of-a-friend I could meet and started learning about other professions. What was available? What was interesting? What would provide challenges for more than a few years?
That exploration led me to coffee with Ellen Chisa, who was at the time a product manager at Kickstarter.
💁 ☕️ 🙆
In listening to her talk and in reading about her profession, I could tell Product Management was the role for me!
- The role overlaps with almost every other role at a tech company, so I knew I’d be able to expand my skill set in all directions there. After developing PM competency, I could go deep in design for a year or two. Or marketing. Or development. Or, or, or…. all of the things. There will always be opportunities to grow around this role.
- The tech world itself is expanding far faster than any individual could keep up with, and any one company will only be addressing a small slice. There will always be outward growth opportunities in this career.
So, my sights were set and once again I was back on the application train.
🚂 📝 💻 📤
No one called me back. Once in a while I got a foot in the door from a warm intro, but no one knew what to do with me. Art history grad with gallery experience seeking a role in tech. Talk about your square peg in a round hole!
After a few terribly unfruitful months of that, I decided to just make a square hole for myself and started my first company.
Of course “company” is a strong word for a nights-and-weekend project with no customers, no revenue, no investors, and no serious business model 😜 But I took myself seriously, and by doing so learned much more about the space than outside observation could have ever taught me.
When it was clear that company wasn’t viable, I let it go and joined a new acquaintance on a side-project-company that at least had some revenue.
👫 📲 💸
That company also shut down — or did it simply never turn on? In any case, I was once again unsure of how to move toward my goal.
Why not actually move? Maybe the issue was the tech market in NYC was too young, too small, and could only afford to hire experienced employees? What about the Bay Area with all its golden opportunity?
Once again I moved across the country without a plan. (Once again I had a romantic partner living there who was willing to support that decision and offered a place to stay while I sorted things out.)
Almost as soon as I landed, a friend connected me with an opportunity. A real tech company. With employees. And a product. And seed funding in the bank. And… based in NYC.
I wanted product experience, and they needed someone to do All of the Things™. So we negotiated a role that would allow for both and I joined as a remote employee.
💁 … … … 👫
The worst. The absolute worst. I was working from home. Alone and so, so lonely. I had no idea how much I needed a team around me, but wow did I learn. I didn’t even last a year before I started looking for local jobs.
A cold email to another PM celebrity, Jackie Bavaro, turned into an interview at Asana. Given how little experience I had, they couldn’t offer me a full time position, but they did extend an apprentice-to-hire opportunity, and I leapt for it!
Four exciting months later, they decided their staffing was too junior to bring me on full time.
But fortunately, that reality led to coffee with Neil McCarthy where we talked about opportunities at Yammer. And from coffee to interview to offer to the best job.
The rest of the story? Well, I’m still writing that….