Hillary Frank gets the best fan mail. “Your book was absolutely amazing!” wrote one teenage admirer in 2003. “Every time I read a book I mark pages I want to go back and write down in my journal. That was hardly possible with your book. I marked about every other page! The words, the humor, and the romance . . . everything was so real.”
Best of Chicago voting is live now. Vote for your favorites »
“I did relate to Jake,” says Frank, who grew up in Brooklyn. “As a little kid I didn’t talk a lot. That kind of freaked out adults, and kids tended not to talk to me or even look at me or say hello, because I really didn’t fit in. I had a hard time asking for anything I needed. I was so quiet.”
She wasn’t so retiring when it came to her schoolwork and her budding art career, which she describes as “more of a math problem: what are people looking for and how can I give them what they’re looking for?” When she was 12 or 13, she says, she won a drawing competition sponsored by Crayola. “It’s a scholarship competition, and it goes to two people in two different age groups,” she says. “I won for the older age group. There were 30,000 applicants.” The company awarded her a $50,000 scholarship. “That’s how I got to go to Tufts,” she says. “My mom and I were talking about ideas that might work, things that the Crayola people might like. For the contest you had to name what your wish was. My mom said, ‘They probably want something like ending world hunger, something like that.’ And I said to her very seriously, ‘No. I’m going to draw about: I wish everything I draw would come to life.’ I thought, you know, it’s Crayola. I figured they wanted people to do something related to their product.”
“I called him up using my answering machine, when they still had microcassettes in answering machines, and I taped him,” she says. “And I took a boom box and read my script into it, and then I fed his tape from the microcassette into the boom box and onto the regular cassette. I even did little internal edits–you can hear the clicks on the tape.” She FedExed it to This American Life, and, she says, “two days later I have this message on my answering machine from Ira Glass saying, ‘You made this thing sound just like one of our stories! How’d you do that?’”
Despite her modest success, Frank continues to struggle with that herself. To make ends meet she’s teaching writing workshops for high school and college students, as well as to middle schoolers through the Chicago Public Schools Literature Magnet Schools program. And she still has trouble paying the rent. “For most of this year,” she says, “I’ve wondered if I should just quit doing this stuff and get a real job, because it felt like just to scrape by I had to work so much that it wasn’t fun anymore. I was working on the book, ‘Chicago Matters,’ and teaching at Loyola all at once. I worked 12- to 14-hour days for about nine months, with no weekends off. And aside from not making much money, it was tough to concentrate on any of those things when I had to keep switching from one to the other. It really didn’t feel worth it to me because I was going crazy.
