Photo: Hische: John Madere; Lettering: Jessica Hische; Moonrise Kingdom: Courtesy of Focus Features; This Is How: Courtesy of St. Martin’s Press

Forget artistic freedom for San Francisco based letterer and type designer Jessica Hische, nothing is as liberating as being penned in. "When you're drawing a picture, the opportunities are almost too endless," Hische, 31, says. "Letters provide constraints that actually make me more creative. The asymmetry of the capital R, for instance—the round bow, the straight stem, the leg—there are so many places to add pizzazz."

Hische's love of lettering grew when she was a graphic design student at Tyler School of Art at Temple University. When her postcollege freelance gigs left her less than inspired ("I admit it: Illustrating calendars wasn't my dream job"), she launched a side project, Daily Drop Cap, a blog where each day she posted one newly designed character: an A sprouting flowers, a B full of flames, a seashell-shaped C. "The site was a place to experiment with palettes and shapes," she says, "and have fun!" As Hische doodled her way through the alphabet 12 times, her work caught the attention of eventual clients like Penguin Books and director Wes Anderson, who enlisted her to compose the credits for his 2012 film Moonrise Kingdom.

Whether she's dreaming up a bold new font or concepts for Starbucks, American Express or Tiffany & Co., Hische initially brainstorms with words. "For a cover of Marcel Proust's Swann's Way for Penguin, I scribbled down words from the book—trees, darkness, tea," she says. "The result was a P for Proust curling out of a teacup—a wink to readers." But while Hische has grown accustomed to working with big-name companies, a recent project caters to an altogether different audience: her first baby. "I decorated the nursery with a bird-inspired series—A for albatross, B for bluebird," Hische says. "I want my kid to get into the letter groove early on."

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