Why I Rock the Boat

And why I will never stop

My first real job outside of babysitting was shelving books at the Oak Park Public Library. I loved it. It was like being a fly on the wall of everyone’s reading habits. People’s returned books told little stories of their own: who’s into self-help, who’s having a midlife crisis, and who’s definitely trying to impress a date by checking out Dostoevsky.

The crew in the back room was great—super chill, no weird politics, just people who loved books and didn’t mind the smell of musty pages. Even Jennifer, the manager, was lovely. She treated me like a person, not just a kid who barely knew the Dewey Decimal System.

One day, Jennifer told us about a higher-paying position that had just opened up. It involved scanning and sorting books for other libraries, and we all had a shot at it. Cue my first real taste of workplace drama.

When it was my turn to interview, I got called into this swanky office on the top floor. It overlooked Scoville Park, which felt very “head honcho” for a job that paid slightly above a teacher’s salary. The guy interviewing me was a family friend—one my mom wouldn’t stop raving about—so I felt pretty relaxed.

The questions were straightforward until he hit me with this curveball: “Do you have any loyalties to Jennifer, or can you follow my lead instead?” It was so out of left field that I just nodded and said, “Sure,” like the clueless 19-year-old I was. He grinned like I’d just handed him a winning lottery ticket, told me I had a bright future, and threw in a “Give my best to your mom!” for good measure.

The next day, Jennifer told me I got the job—but she didn’t look happy about it. No smile, no “Congrats, kid!” Just a weird, heavy vibe that I didn’t understand at the time. I was too stoked about affording a Lollapalooza pass to think much about it.

Fast forward a few months: Jennifer was let go. The department head came downstairs, beaming, and told me I had a managerial future ahead of me. He even recycled the “Give my best to your mom!” line, which hit differently this time.

That was my crash course in how the world *really* works. I didn’t get the job because I was the most qualified—I got it because I played along. I went home and told my mom I thought her friend was sketchy. She brushed it off, saying he was a Quaker and on the Peace and Justice Committee, which is *so Oak Park* I could scream.

After college, I landed a marketing job at a big company. Same story, different setting. All I had to do was make the right people feel important, and I was golden. I was making money, climbing the ladder, and living the dream—or so I thought.

But then it hit me: I wasn’t changing the world; I was just decorating its walls with corporate buzzwords. So, I pivoted to tech—disruptor culture, innovation, all that jazz. It felt like a fresh start, like I was finally doing something meaningful.

Except the more I disrupted, the more I started questioning everything. My beliefs, my friends, even my own family. I realized that the so-called “status quo” I thought I was rebelling against? I was part of it. Worse, we weren’t just maintaining it—we were gatekeeping it.

So, I did the unthinkable: I started trying to understand people who didn’t think like me. Republicans, specifically. Were they the monsters I’d been told they were? Turns out, no. They’re just people who love their kids and their country, which, spoiler alert, isn’t that different from Democrats.

This journey has been brutal. People have called me a sellout, a conspiracy theorist, even dangerous. But I’m not giving up. At the end of the day, it’s all about the same thing: corruption of the spirit. And I’m just out here, trying to get people to think a little more clearly about why they believe what they believe.

It’s exhausting, but hey—at least I got to see The Black Keys that summer.