For many people, storytelling is a form of connection. For Ilana Peña ’09, it’s a way of life.
Ilana’s path to becoming the creator and executive producer of Disney+’s “Diary of a Future President” began with a move, a journal and a swirl of life changes. “When my mom began looking at middle schools for me and my brother, she landed on Pine Crest,” Ilana said. “We had just moved from North Miami Beach to Weston, my mom got remarried and I suddenly had two new step-siblings. All of this happened in two weeks.”
To make sense of it all, Ilana turned to writing. “I kept diaries because so much was changing—I had to write it down,” she said. “I was always a storyteller. Even before I could write, I loved an audience. As soon as I found writing, I fell in love with it. I’d create books using Microsoft Word and Clip Art with ‘About the Author’ pages because, clearly, I took myself very seriously,” she joked.
But beneath the humor was a deeper motivation. At five years old, Ilana lost her father unexpectedly. “That kind of thing is tragic for anyone. But at five years old, I just didn’t understand it. So I turned to acting and writing to help me process those feelings and work through the grief.”
Ilana threw herself into the performing arts, from plays at the Florida Children’s Theater to musicals at Pine Crest. “I even got to be in the Upper School musical ‘Gypsy’ as a middle school student, which felt like such a flex,” she said. “But eventually, I stopped children’s theater to focus on Pine Crest musicals. That became my community—the people I connected with then are still my closest friends to this day.”
Teachers at Pine Crest also nurtured Ilana’s creativity. In Middle School, English teacher Eleanor Brown encouraged Ilana’s writing. By the time she reached Upper School, she was co-editor of the newspaper, wrote for “The Scribbler” and co-founded the Drama Club with her best friend Kelsey Flynn ’09. “My first script, which I wrote for Spring Scenes, was a sketch spoofing ’90s teen dramas. That was also the first time I wasn’t on stage but behind the scenes, writing, directing and producing.”
Senior year provided Ilana with another defining moment: directing a student-led production of “Romeo and Juliet” with Kelsey. “We reworked the script, cast it and produced it ourselves. That was my first taste of being a writer, director and producer all at once.”
Ilana took that momentum to Northwestern University where she majored in theater. “I wanted to do it all—act, write, direct. But I took a playwriting class freshman year, and slowly the writing took center stage.” She joined a two-year Creative Writing for the Media program, produced a play and by senior year, had dropped acting classes altogether. “I found a clear career path in TV writing. My Pine Crest brain really latched onto that.”
After graduating in 2013, Ilana moved to New York but quickly realized it wasn’t the right fit. “I had always felt like the expectation is that you stick it out. But that doesn’t have to be everyone’s journey.” Something Ilana realized after a single visit to Los Angeles changed everything.
There, she worked as a writing assistant, hustling through a string of jobs. A pivotal opportunity came when she joined the staff of the CW’s “My Crazy Ex-Girlfriend” in season two. “It was my fifth job out of college—not my first. After all the grinding, I finally landed somewhere that allowed me to work for some phenomenal women bosses who also promoted from within.” Ilana eventually rose from assistant to official staff writer on the show, and became a member of the Writers Guild of America.
Then came a significant breakthrough. During season four of “My Crazy Ex-Girlfriend,” Ilana managed to sell her own show. Inspired by her own Miami upbringing, “Diary of a Future President” follows a 12-year-old Cuban-American girl navigating middle school, on her way to becoming president. Gina Rodriguez and her production company championed the show and Disney+ picked it up for a straight-to-series order. It debuted on January 17, 2020.
“Honestly, as exciting as it was, I was also overwhelmed and nervous. There was a voice in my head saying, ‘You’re not ready yet.’ But it was my work—my story. I had the vision, I knew what I wanted and I had all the answers,” Ilana said. “It was ironic: I was writing a show about a girl becoming a leader as I was becoming one myself. Learning how to stand in my own power just as she was is what ‘Diary of a Future President’ is all about.”
In 2021, Forbes named Ilana to the “30 Under 30 in Hollywood and Entertainment” list. But for Ilana, it wasn’t just about the accolades. “I think professionally it's always nice to have recognition, but at the end of the day, what matters more—and what I've found has really led to opportunities—is my passion for projects and the relationships I've formed.”
A life of storytelling has given Ilana a rich perspective, and she hopes to continue to inspire younger generations of students through her work. “If I could give young people any advice, I’d tell them to give themselves grace. Be open to change and the unexpected, and while you’re working hard remember not to take yourselves too seriously. High school and college are the times when you explore who you are, but you can’t do that if you’re not seeking joy. That’s how you’ll find your story, and maybe even share it with the world.”
