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.”

“Dear Miss Hillary,” wrote another in September. “First I want to thank you for opening my eyes in a whole new way. Your book . . . was so shoking and theres no words 4 it, it has become my favorite book, exept 4 the wanderer, but i think your book is winning by a lot. . . . I never thought this book was going 2 be about sex . . . it shocked me at first but then i got so into the book. I finished it the day i rented it. At some points i really wanted 2 be Ellie. It opened my eyes in a way no other book could.” She signed her e-mail “Love and Hope, The Changed One.”

Both of those messages came in response to Frank’s first book, a young-adult novel called Better Than Running at Night. Published in 2002, it tells the story of a high school misfit’s coming-of-age at art school. Her latest book, I Can’t Tell You, the first new work to be published by Houghton Mifflin’s new YA paperback imprint, Graphia, is set in the same swamp of adolescent insecurity and confusion. The protagonist, Jake Jacobsen, has forsworn talking after a nasty fight with his roommate, and his strangled attempts to express his feelings to the girl he adores play out entirely through notes, e-mail, and the occasional pictograph. It’s a spot-on manifestation of the paralysis of desire.

“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.”

Since then she’s approached her professional life with that same analytical force and determination. When she decided she wanted a literary agent this past August, she looked up John Hodgman, author of an irregular column on the McSweeney’s Web site called “Ask a Former Professional Literary Agent.” “I don’t think anybody ever asks him about literary agent stuff,” she says, “but I got his e-mail address and asked him if he thought I needed an agent.” He said yes, and recommended her to one at Writers’ House, who in turn recommended her to his colleague Steven Malk, who took her on as a client in September. “It turns out,” she says, “he’d been following my career for a while. I was like, ‘I didn’t know I had a career!'”

Frank, who’s 28, stumbled into YA publishing shortly after she graduated from Tufts in 1997. She’d enrolled in a dual degree program in English and studio art, but she soon became frustrated with the school’s conceptual-art emphasis and found herself more engaged by writing. When she graduated, she thought she might be able to combine the two by writing and illustrating books, so a teacher sent her to a friend who made children’s books. The friend read Frank’s short stories, plucked out one she thought particularly promising, and told Frank to send it to Eden Edwards, an editor at Houghton Mifflin.

After a few months Frank hadn’t heard from Edwards. So she called her up. “She was like, ‘Hillary, it takes people a while to get back to you if we really like something. You have to be patient,'” says Frank. “A couple of months later I get this letter from her with just all these questions: ‘Why are the parents of this character not in the story? Why does she feel this way about boys?’ And ‘If you want to turn this into a short novel or a collection of stories, I’d like to talk to you again.'” That correspondence led to Better Than Running at Night.

In 1998 Frank moved to New York to study figure drawing at the New York Academy of Art. While she was there, she decided she wanted to be on the public radio show This American Life. “I kept sending in scripts of essays I wanted to get on the show and I was getting rejection after rejection,” she says. “I think I was rejected like five times.” She took matters into her own hands, producing a 15-minute radio piece on a friend who was obsessed with the end of the world, using the technology at her disposal.

“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?'”

Frank didn’t tell Glass that her writing had already made an impression on him. “There was this big article in the New York Times on Ira and the show that year,” she says. “I was so excited to read it. In it they talked about the huge slush pile of stuff that gets rejected. And in trying to list the awful first lines of things they listed one of mine: ‘Love was not for Sam.’ It’s a really terrible first line. I was pretty embarrassed.”

Her DIY piece about apocalypse angst never made it on the air, but Glass commissioned another from her in the same style, and in 2000 Frank wound up in Chicago as a This American Life intern. Since then she’s been living on the north side, patching together a living writing, teaching, and producing work for public radio. Two weeks ago she won an honorable mention from the Third Coast Audio Festival for a piece coproduced (with Amy Dorn) for WBEZ’s “Chicago Matters” series. Titled All My Stuff in Bags, it’s an eight-minute documentary about an 18-year-old boy whose father kicked him out of the house on his birthday for being gay.

Frank didn’t intend to specialize in teen angst. But when she wrote Better Than Running at Night, she says, “I was a YA myself. I was 19 or 20 when I first started writing in college, so I was just writing about what was going on.” Since then, much of her favorite work has explored coming-of-age in one form or another.

“I think on a very basic level, it’s because no story is a good story without some sort of conflict and change–and there is inherent drama and internal conflict in coming-of-age,” she says. “Coming-of-age can also be a great equalizer: it’s an experience that anyone who’s been a teenager can relate to. I mean, the details are unique for each person, but there’s nobody, no matter how confident, that hasn’t struggled with the question: Who am I and what am I becoming?”

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.

“The thing that’s kept me freelancing is that I’m hoping the agent will help . . . and those fan letters. How can you quit when your fans are kids and they tell you that your books are keeping them sane, changing their lives?”

Art accompanying story in printed newspaper (not available in this archive): photos/Jim Newberry.