From Law to Comedy

As a first-generation college student from a working-class family, Cauley learned to think critically on the Madison campus. Mindy Tucker

Kashana Cauley ’02 majored in economics and political science at UW–Madison and graduated from Columbia law school, but she credits X (formerly Twitter) with the education that forged her career. Unhappy with the hours and stress of practicing antitrust law for a Manhattan firm, Cauley started writing jokes on the social media platform. She kept tinkering with her style until she found her now-characteristic acerbic wit. “It was a good medium,” Cauley says. “You had to be short and punchy— say something funny in just 140 characters — and you could see what worked live and what didn’t.”

X also delivered her unexpected career break. After putting her jokes out there and writing an essay for the Atlantic about how becoming a mom converted her from an early anti-vaxxer stance, she received a message asking her to write for The Daily Show with Trevor Noah.

“It was a Saturday at 3 a.m. — it was so obviously fake,” she said of her initial reaction. But the offer turned out to be real. That led to the fulfillment of her childhood dreams to be a writer and to do comedy. She’s followed that up writing for The Great North and Pod Save America. She’s also written for the New York Times, Esquire, the New Yorker, and Rolling Stone, among other publications. Now she’s writing novels.

Her debut, The Survivalists — a dark comedy about a young Black lawyer risking her career and conscience to move in with her doomsday-prepper boyfriend — made multiple best-of-2023 lists, including Marie Claire’s and Ms. magazine’s.

This past summer, she published The Payback, described by the New York Times as “a novel that takes on our absurd, predatory student loan system with a zany sense of humor.”

Cauley jokes that she was able to draw upon her personal experience with higher education in writing about student loans. “The UW was responsible for making some of that debt possible.”

Seriously, though, she says she’s indebted to the university for more than student loans. As a first-generation college student from a working-class family, Cauley learned to think critically on the Madison campus. “It made me the thinker I am today,” she says.

Cauley is at work on another novel and says she’d welcome the chance to write for TV again, employing her characteristic biting satire to address the systemic injustices that trouble her. “You can lecture people,” she says, “but if you put jokes in there, they’ll be laughing and maybe realize they have learned something, too.”

Published in the Winter 2025 issue