When I Was 17: Jake Levy-Pollans

Jake Levy-Pollans is the senior director of strategic services at Trilogy Interactive, a consulting firm working with campaigns and causes across the country. While his goal had always been to work in politics, Jake and I first bonded over our shared interest in college admissions. Jake is one of the most enthusiastic alums I’ve ever met, first working as a teenage tour guide and now interviewing prospective students and representing Macalester at local college fairs. And if you asked him, I think he would say Macalester did a lot to develop him into the professional, and the person, he is today. Our conversation has been edited for length and clarity. 
 
When you were 17, what did you want to be?
 
I thought I wanted to work in politics. I come from a family that’s really political. My dad would read a New York Times article and we'd fight over it at the dinner table. And I took some great high school classes and had some great mentors. I wanted to have a role in the political system and the way the government can make people's lives better.

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I was lucky enough in high school to have the opportunity to intern for the Ann Arbor mayor's office, and I had a civics class that took me to New Hampshire to work on a presidential primary. In the summer going into tenth grade, I was at a farmers market and a local candidate for congress had a booth; I remember she had dog treats at her booth and I was kind of intrigued by that. I don't know what made me think of it, but I asked if she needed an intern for the summer. And she said, "Yeah, sure, I'll put you to work." I spent probably 50 or 60 hours a week in that campaign office. I made lots of phone calls, I assembled lawn signs, I helped plan events, I did as much as I could as a 15-year-old without a car, and I started learning what being an organizer was like. And I was way better at that than sports.
 
So at 17, I knew that there was a campaign side of politics that was about who gets elected and how you run a campaign and the stories you tell and the issues you take up, and there was the government side of it that was about getting elected and serving people. I honestly don’t know that I had a strong preference for one or the other; I thought that both had a lot of value and were challenging and engaging and I was sort of open to the journey toward one or the other, and honestly, I assumed that over the course of my career, I'd do a bit of both.
 
How did you decide to attend Macalester College? 
 
I grew up in Ann Arbor, Michigan, home of the University of Michigan. I lived five blocks from The Big House, the University of Michigan's football stadium, the biggest football stadium in the country. I could hear the cheers from my house - I always knew Michigan had scored a touchdown before you saw it on TV.
 
I'd seen Michigan my whole life, a Big 10 school, 40,000+ students, great sports, great research university, and I wanted the exact opposite. I wanted a school that nurtured intellectual curiosity and explored how that could impact the world around you, and I wanted to do that with a bunch of other super curious people.
 
What I loved about Macalester is that everyone's passionate about something. They were passionate about researching bugs and how that could be used for cancer treatment, or how Shakespeare really stole 80% of his content from somebody else. I just wanted to be stimulated every day, and Macalester seemed like a passionate, engaging place. Also, the food was really good, some of the best burritos of my life.
 
How did you choose your major? 
 
I knew I liked politics, so I took some political science classes early on and I liked them, but I knew that you didn't have to study political science to work in politics. You can be an English lit person and become a great writer, or you can study Hebrew...the whole point of a liberal arts education is that you can dive into a passion and figure it out after that.
 
So I took a lot of political science classes, but I went to a college with 1900 students and the course catalog had 600 courses. There's a course for every three kids at Macalester. There was just a world presented to me that was weird and interesting and quirky. Like I took a Geology 101 class that was all about dinosaurs. Part of our final exam was to watch Jurassic Park and write about what was wrong with it. It put this science nerd in me, and I almost ended up minoring in geology because of that. It was a reminder that you can have a plan and know what you're passionate about, but the whole point of going to college is to find some other stuff too.
 
How did you get from college to where you are now?
 
I had worked all four years of college. I had been a tour guide because I like Macalester, I don't mind walking backwards, and I loved having moms laugh at my corny jokes. The summer going into junior year, I applied for a Macalester fellowship that funds you if you take an internship at a nonprofit or an advocacy organization in the Twin Cities. I got a position at a nonprofit and set up my first ever real communications plan. That internship helped set me up in the work that I did post Macalester.
 
The founder of the nonprofit I had worked at decided that he wanted to run for governor, and we were close by then, so I started interning for his campaign my senior year. He was organizing out of his house which was a block from campus, so it was all very easy. I always thought that they would give me a job the day I graduated, which in retrospect was a fun assumption. I'll never forget, the campaign manager and the candidate took me out to coffee three weeks before graduation, and they said, "We love you and we're so excited to bring you on board, but we're not going to be able to do that for another seven or eight months."      
 
I wanted to stay connected to the campaign and be available whenever they were going to be able to hire me. But I also needed to pay my rent and pay for the baked potato I needed to eat every once in a while. I'm so glad I didn't get that job right out of college because I got to do some random stuff and it was so fun!
 
I DJ'd weddings – my name was DJ Dr. Dreidel, which not everyone in the Twin Cities got it turns out. I nannied for two awesome kids. On Saturday mornings, I interviewed perspective Macalester students. I interned at a PR firm just to find out what a PR firm does. I learned so much from each of those individual experiences. And then I jumped on the campaign as soon as they could hire me. I traveled Minnesota on behalf of this campaign as the traveling press secretary, and I really got to know the state and learned how to communicate to the press.
           
I made a lot of really terrible mistakes in retrospect. Sometimes you have to accidentally send a press release that has the wrong date for an event, the wrong location for the event, and the wrong speaker for that event all at the same time to learn that as a 22-year-old, you're not perfect. Luckily enough, I had a boss who gave me a really hard time for it, but also didn't fire me.
 
After that campaign, I was lucky enough to get hired by Obama at the end of 2011 to work on his re-election (I should be clear that Obama didn't personally hire me). A bunch of friends were working on the re-elect, and there was a position for a digital director in Minnesota. They asked me, "Do you know what being a digital director is? Can you do that job?" And I said yes, and they said, "Great, you're hired.” I remember the first day on that job, I needed to make a graphic with a picture and a quote, and I didn’t even know basic Photoshop. So I went to the University of Google, and spent the next year figuring everything out and doing it for Barack Obama, which is a pretty cool way to do it.
 
I worked on that campaign for almost exactly a year. I got some really great Obama swag, I made some of my best friends, I drove around rural Minnesota with other campaign staff in an RV that we wrapped in the Obama logo and just tried not to wreck.
 
After the campaign finished, I had three or four great months of funemployment. I highly recommend funemployment to everyone. When you work in campaign politics, you have to be prepared to not have a job for a while. There were days I didn't go outside, days I didn't put on pants, I watched Friday Night Lights from start to finish, just had a great time.
 
Then I got a job with an organization called Wellstone Action that trains people to run progressive campaigns, either as the candidate themselves or as the campaign manager or staff. I helped that organization think through how to use the Internet to train more people through online classrooms and online libraries, and also how to train people to use the Internet to be effective campaigners. Like how do you organize on Facebook, how do you raise money over email, how do you persuade voters through YouTube videos.
 
I worked for them for three years, and for the most of my life I’d lived in Minnesota or Michigan. In my mid-to-late twenties, I decided I wanted to live somewhere else. I had a bunch of friends in the Bay Area, and every time I visited, I’d think, "I want to live out here sometime." Wellstone was a really generous place and they let me work remotely, so I told them I was going to work from the Bay Area for a while. And after that organization gave me all the trust to move out here, I realized within a few months that working remotely was not my jam. I need an office with other humans.
 
So I got hired at a political consulting firm in the Bay Area called Trilogy Interactive, working for some of the biggest progressive advocacy organizations and the more significant political leaders in the progressive movement. It seemed like a new challenge.
 
I’ve been helping lead the charge at Trilogy for the last two and a half years. My job is to help clients think through what they need to do to win, what their goals are, and what reaching those goals might look like. I guide a team of really brilliant creative people and production folks and coders and developers to execute those goals for the campaign or the organization, and stay connected to those campaigns, so they know how things are progressing.
 
Looking back, what seems clear to you now? 
 
Some people have a five-year plan, and some people figure out their next plan when they need the next plan. I've been super fortunate to build this really great career, and I think 17-year-old me would look at what 31-year-old me is doing and say, "That's about right." 17-year-old me had no idea how to get there, but I've been really fortunate that it's worked out, and I figure the next step will probably work out too.
 
It's not just okay to not know what's next – you should celebrate it. After college, I'm so glad I didn't totally know how it was going to work out. I'm not just asking you to be comfortable with not knowing, I'm asking you to enjoy it. There are so few times in your life when you get to enjoy that freedom. So embrace it.
 
Also, baked potatoes are a perfectly acceptable meal.