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.

​Christopher Kempf is a poet, writer, and English PhD student at the University of Chicago. His first collection of poems, Late in the Empire of Men, was published in 2017 after being awarded the Four Way Books Levis Prize. I first met Chris a few years after I had given up my own aspirations of becoming an English professor, and hanging out with him provided me with the casual references to Sartre and Walter Benjamin that I had been missing. Interviewing Chris reminded me once again of the pleasure of a life spent reading and writing and discussing things. Our conversation has been edited for length and clarity.
 
When you were 17, what did you want to be?
 
I don't think I thought so much of a career; I thought more of what classes I liked in high school, and from a very early age I had great English and history teachers. I wasn't very practical about my college education and what I wanted to be. I didn't quite envision a college education as a transition into a job. My parents wanted me to be a lawyer, which I considered, but I guess I just always privileged doing what I wanted to do and studying what I wanted to study more than how that would slide into to a job.

Scott Reardon is an actor, performer, and designated teacher in the San Francisco Bay Area. Scott and I met in high school while doing community theater (fun fact: he was also my first boyfriend), and we all had fantasies of growing up to be Broadway musical stars. 15 years later, Scott is actually doing it – making his living as a professional actor. But just as with any profession, the reality might look different from the version you imagined in high school. In fact, it might even be better. Our conversation has been edited for length and clarity.
 
When you were 17, what did you want to be?
 
Growing up, it was always a lawyer, doctor, that type of thing. Prior to high school, I had no idea about theater, no one in my family is artistic. When I did the first show with Harmony Players, Grease, that was my first intro to theater and that's  when the bug bit, I would say. But I didn't think I was going to do it as a career, even though I did it all through high school and my first job was performing for Nickelodeon at Great America (a local amusement park).

​Vikrum Aiyer is the vice president for public policy and strategic communications at Postmates. Before joining the tech world, Vikrum spent 10 years working on policy and communications for the Obama administration, Hillary Clinton’s first presidential campaign, and then-Congressman Ed Markey. I’ve known Vikrum since the fourth grade, and it should have been obvious that he was destined for a career in political speechwriting and communications when he ran for and won the election for senior class president using the slogan, “I’m hella legit.” Our conversation has been edited for length and clarity. 
 
When you were 17, what did you want to be?
 
When I was 17, I was oscillating between a few things. I thought I might want to be a psychologist. I was kind of interested in being a karate instructor. I did taekwondo for six years. I didn't study it so much as that my parents forced me to go to classes. I'm not very athletic. I thought that I wanted to maybe become a journalist, but I think really what it was was that I was so intrigued by high school speech and debate, and that there was a forum in which you could exchange ideas, and also kind of recognize that there's no one worldview, that every issue has multiple sides. That sort of led me to this belief, whether it's true or not, that being a lawyer is the professional version of being a high school debater. I think at 17, that was sort of the path I was thinking about.

​Charles Boucher is a managing partner at Boucher-Lensch Associates, a Silicon Valley-based investment banking firm. And no, the name isn’t a coincidence; he’s also my dad. It’s hard to imagine that your parents had a life before you were born, which made it all the more enjoyable to hear my dad talk about himself at 17, and hear his stories about getting in trouble for doing his chemistry homework in the middle of French class. Although I came into our conversation knowing the general twists and turns, the real pleasure was in hearing him explain it to me. Our conversation has been edited for length and clarity.
 
When you were 17, what did you want to be?
 
I'm not sure I had a really clear idea of what I wanted to be. I knew I wanted to be in some kind of successful job. I wanted to be in a white-collar business, because my parents never came close to that. I wanted to wear a suit and tie. That was always the image of success that I learned from television, from commercials and movies, from watching my friends' parents who had engineering jobs or business jobs. So I knew I wanted to do something like that. And I thought it was probably going to be in some type of technology. I always had a predilection for science and math. I would sit in French class in high school, working on my chemistry homework. But I really didn't know what I wanted to do.