From 2017 to 2021, Bowles covered technology and culture for
The New York Times, mostly while based in the
San Francisco Bay Area. In 2020, she received the
Robert F. Kennedy Journalism Award and the
Gerald Loeb Award for investigative reporting along with two colleagues for her investigation into
online child abuse; according to editor Dean Murphy, their "deep, persistent and compassionate reporting" served to "hold both government and big tech accountable, and tell the stories of untold children who have endured this abuse in silence." Bowles covered the technology and business world of high-tech startups and venture capital, and has written about personalities such as
Elon Musk, and iHeartMedia CEO
Bob Pittman. She covered the exclusive conference of technology CEOs called
Further Future, and has written about subjects such as
doxxing and
cryptocurrency. She appeared twice on the
Charlie Rose show. Bowles's reporting is often controversial; for example, her account of her interview with
Jordan Peterson attracted much attention. She has moderated televised discussions on
free speech in the digital age, and has written about
gender equality in the tech world. Her reports on the conflict between Israelis and Palestinians have sometimes generated additional controversy.
Harvard professor and legal scholar
Lawrence Lessig sued Bowles and
The New York Times for defamation over her reporting on Lessig's writings about
Jeffrey Epstein's donations to the
MIT Media Lab in the
Times. Lessig dropped the suit after the headline and lede were changed to better represent his views. In January 2021, Bowles and
Bari Weiss launched the online newsletter
Common Sense. The publication was renamed
The Free Press in 2022.
The Free Press is now the top-earning Substack publication, with more than 1,740,000 subscribers. Bowles is the company's head of strategy and writes a weekly column called TGIF, a satirical roundup of current news. Her
New York Times story "The Sperm Kings Have a Problem: Too Much Demand" was turned into a feature-length documentary, produced by the
Times and FX and released in 2024. It served as the inspiration for
Lance Oppenheim’s
Spermworld. Her first book,
Morning After the Revolution, was released in 2024 by Thesis, a new imprint of Penguin Random House. In the book, Bowles alleges that many U.S. institutions, including the governments of large cities and legacy media outlets, have been captured by far-left political actors. In
The Washington Post,
Becca Rothfeld wrote, "The book's ambient contempt for progressives is legible; its actual thesis much less so." Commenting on the book's factual inaccuracies in
The Guardian, Charles Kaiser wrote, "Fortunately for her—but unfortunately for us—her publisher, a new Penguin Random House imprint, Thesis, does not appear to impose any outdated fact-checking requirements. The only visible standard here is, if it's shocking, we'll print it." Comparing Bowles unfavorably to
Tom Wolfe in
The New York Times Book Review,
Laura Kipnis wrote, "where Wolfe was a precision-guided stiletto, Bowles is more of a dull blade, ridiculing her former colleagues by saddling them with laughably vacuous thoughts and dreams." Kipnis concludes her review, "the book's central fallacy is that idiocy on the left requires moving to the right. It doesn't. It's eminently possible for people with brains to make distinctions and stick to their principles, if they have any. And, by the way, you're not going to find any fewer authoritarians and idiots by switching sides." == Personal life ==