Hawai‘i Writers Almanac: Constance Hale

A companion to our feature “The Hawai‘i Writer’s Life.”

A companion to our feature The Hawai‘i Writer’s Life, this compendium of writers, platforms, resources and more intends to map out our literary communities and individuals. It’s just getting started, but we hope it will grow to help them, and you, find each other, scheme together and maybe get some writing done. 


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WHO: Constance Hale, bestselling author and grammarian, writing teacher.


WHAT: Two books on grammar, a book on a revolutionary hula hālau.


WHY: Many writers set out to write a bestseller and fall short. Fewer writers write books about how to write. Only a couple dare write about grammar specifically for writers—E. B. White and William Strunk most prominently and, lately, Connie Hale.


The way the Levi brothers got rich selling spades, pickaxes and denim jeans to gold miners in California, Constance Hale became an accidental bestseller, frequently quoted by national columnist George Will, for a pair of copy editing and style handbooks. “And I didn’t think of myself as a writer growing up as a kid in Waialua,” she says. “I went to Hale‘iwa Elementary!”


Hale was smart enough to get into Princeton, but dropped out. “Too great a cultural difference,” she says. “But before I dropped out I switched my major from American Studies to a more creative program. And then I learned how to waitress and by the end of the year I knew how to live a bohemian life.”


She went back and got her degree, concentrating on poetry and going onstage for solo monologues. After opening and running a restaurant with a chef—at age 23—she decided that writing mattered more. But instead of getting a master’s in arts and looking for poetry teaching gigs, she went back to school for a master’s in journalism. She started as a reporter at a tiny California paper, then to the Oakland Tribune, where she switched to the copy desk. She was good at fixing other people’s stories, it turned out. When Wired Magazine, a brand-new startup in Silicon Valley called, she went to work there.


“That was a huge lucky break,” she says. Rising quickly to assistant managing editor, she told her bosses, “Hey, we ought to take our style manual and make a book out of it.” The result, Wired Style: Principles of Usage in the Digital Age, “did really well—it was an Amazon bestseller when Amazon was new.”


Now “somebody in the very small pond of language mavens,” as she puts it, she left Wired, went freelance, and 10 years later wrote another book on language: Sin & Syntax. “It did OK, solid. Then it started to build into a backlist wonder, getting adopted into large university courses. Every book about grammar was a boring textbook. This wasn’t. Students loved it.”


She spent three years as director of Harvard’s narrative journalism program before moving back to the West Coast. She prefers freelancing. “I make very little money,” she says. “I have very low housing costs because I bought a house in a ghetto. I have been totally saved by Obamacare. I’ve written seven books and only one is successful in the sense of getting a check every March and one every September.”


But, she says: “Most people who are conventional and like security just tank as freelancers. You have to have a little chutzpah. You have to be entrepreneurial. You have to have a head. You can’t be risk-averse and have to have a tolerance for bending the rules. Writers have always been spongers, scammers or trust funders.” (Attention would-be writers: So now you know.)


Hale now splits time between Oakland and O‘ahu, where she founded the Mokulē‘ia Writers Retreat four years ago. The weeklong program in May offers writing workshops for all disciplines and readings; with 30 writers and six faculty, it’s intimate, accessible and spunky as Hale herself.


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Read more stories by Don Wallace