Write About Now

Jon sits down with Andrew Postman (Glamour's "Jake: A Man's Opinion," 1990–94) and Ky Henderson ("The Guy Guru" at Cosmo 2006) to talk about life as male advice columnists for women's magazines in the '90s and 2000s. They swap origin stories — how each landed the gig almost by accident — and dig into the mechanics of the job: where the column ideas actually came from, the freedom, how they came up...

Courtney Kocak grew up a small-town girl in Jackson, Minnesota, dreaming of becoming an actress. But her path to Hollywood led through some unexpected territory: seven weeks on the Girls Gone Wild tour, abusive relationships, an abortion, and eventually OnlyFans. During that time, she also became a celebrated writer, podcaster, and teacher. It's all laid bare in her new memoir, Girl Gone Wild , wh...

Jeff Chang, author of Can't Stop Won't Stop , joins the pod to reminisce about when hip hop moved from park jams to mainstream America in the 1980s. From "Rapper's Delight" to Run-DMC's crossover moment to Rakim changing the flow entirely and Public Enemy making it political, Jeff breaks down the turning points. We revisit the so-called golden era debate, why the 80s deserve more respect, and our...

Joyce Maynard has been writing for 53 years. At 18, she landed on the cover of the New York Times Magazine, caught the eye of J.D. Salinger, and disappeared into a relationship that would define her for decades—until she finally told her story and was called a "predator" by Maureen Dowd. In this conversation, Joyce talks about being canceled before canceling was a thing, surviving as a Me Too surv...

Since its debut on Apple TV Plus,  Pluribus has sparked an unusually intense response. Viewers not only watch it, they debate it and project onto it. Executive Producer Alison Tatlock talks about why the series has connected so deeply with audiences. We dig into the emotional problem at the center of the show, how skepticism shapes its characters, and why discomfort is doing more of the storytelli...

People in their 50s are confronting a financial reality nobody prepared us for. We grew up assuming steady careers, pensions, and a clear path to retirement. Instead, we're juggling layoffs, credit card debt, college tuition, aging parents, and rising healthcare costs, all while wondering what "retirement" even means anymore. Kerry Hannon and Janna, co-authors of  Retirement Bites: A Gen X Guide t...

Former Hollywood TV writer Amy Suto walked away from Hollywood to build a seven-figure freelance writing business. She talks about the 3 pillars that got her there, the Substack tweaks that added $100,000 in value, and why self-publishing can earn more than traditional book deals. Amy's new book is Write for Money and Power: The Anti-Starving Artist's Guide to Becoming a Seven-Figure Writer. Follo...

Lili Zarghami spent decades working in women's magazines before realizing none of them were speaking to women like her anymore. After turning 40 and getting laid off, she decided to create Jenny Mag—a digital magazine for Gen X women who don't fit the cookie-cutter mold of traditional women's media. In this conversation, we discuss why dating stories outperform health content, the complicated rela...

The legendary crime writer talks about how she builds characters, steals voices, mines real communities for detail, and turns dark human behavior into bestselling fiction. We also get into real police sources in London, writing about Nigerian communities and FGM in a way that doesn't get you canceled, and the piece of advice PD James gave her that changed her life forever. Follow me @ jonsmalltalk...

Smartphones and social media have changed childhood in ways few of us could have predicted. For starters, many children are now getting their first phone at just 10 or 11 — far younger than the technology was ever designed for. Once that phone is in their hand, it can interfere with sleep, friendships, independence, and even mental health. So what can parents do? Guest Jean Twenge, Ph. D,  is a pr...

My guest this week is Kaila Yu. Her new memoir, Fetishized: A Reckoning with Yellow Fever, Feminism, and Beauty takes on a provacative question: what happens when you've built a large part of your career in a culture that objectifies you? And how complicit are you in keeping that culture alive? Kaila looks back at her years as a model and musician, and then forward to the harder work of reclaiming...

Captain William Kidd is one of the most famous names in pirate lore. But what if he wasn't actually a pirate at all? In this episode, bestselling author and scientist Samuel Marquis joins me to talk about his new book Captain Kidd: A Story of Treasure and Betrayal.  Marquis has a personal stake in the story — he's Captain Kidd's ninth great grandson. We talk about Kidd's rise from colonial sea cap...

When I helped launch  Twist  magazine in the late '90s, we basically huddled around old issues of  Sassy like sacred texts, trying to decode what made them so special. The answer? Jane Pratt. So it was with excitement and a little nervousness that I jumped on a Substack Live Interview with her. We chatted about: Her miserable boarding school experience and how it inspired  Sassy Getting pulled off...

Historian Hampton Sides joins the show to talk about  The Wide Wide Sea , his riveting new book about Captain James Cook's final—and fatal—expedition in 1776. We get into: Why Cook lost his cool on his last voyage What really happened in Hawaii The crew's wild sexual escapades in the South Pacific What this story reveals about power, empire, and the price of discovery Subscribe to my Substack @ Jo...

Guest Kim Dower has spent the last 40 years helping authors get noticed — as one of the top literary publicists in the business. She's also a celebrated poet, with a brand-new collection out now called  What She Wants . In this episode, Kim pulls back the curtain on what publicists actually do, who really needs one, and the biggest mistakes authors make when trying to promote their work. If you're...

A lot of Gen Xers are facing an existential crisis, feeling stuck, burned out, unemployed, and just unsure about the future. This was supposed to be the time when we start to wind down so why does it feel like we're on a highway to hell? This doesn't mean we're doomed; it just means we need a reset on how we think about retirement. In my first-ever Substack Live  over on my newsletter Small Talk,...

Gretchen Rubin joins the show to talk about her new book, Secrets of Adulthood, in which she boils down a lifetime of wisdom into powerful aphorisms that resonate. Gretchen is a bestselling author, podcast host, and one of today's most trusted voices on happiness, habits, and human nature. In this conversation, we talk about the lessons we learn too late, the advice she wants to pass on to her dau...

When the New York Times declared it was "the end of work as we knew it" for Gen X, it did not feel fine. The story called the generation obsolete, irrelevant, and even likened them to candlestick makers in the age of electricity. Seriously? The article sparked a firestorm, prompting host Jonathan Small to write a viral Substack response that only raised the temperature. Now, Dana DuBois—fellow Gen...

Has anyone ever told you, "Your life is so interesting—you should write a memoir!" It's flattering, no doubt. But then comes the doubts and the fears and the paralysis. How do you transform decades of memories and anecdotes into a narrative people would actually want to read? You can start by reading guest Wendy Dale's new book, The Memoir Engineering System . In it, she gives you the structure fo...

Back in Hollywood's Golden Age, two men with vastly different backgrounds came together to shape the future of film. Louis B. Mayer, a shrewd businessman and Irving Thalberg, a visionary producer, formed a partnership that defined MGM and set the standard for the modern studio system. In this episode, famed film critic Kenneth Turan explores their unlikely partnership, their imperial rise, and the...

The 97th Academy Awards will grace Hollywood this Sunday, bringing its signature blend of glamour and controversy to the red carpet. To unpack all the drama, we're joined by  Katey Rich, Awards Editor at The Ankler and host of the acclaimed podcast "Prestige Junkie." Katey reveals her journey to securing her coveted position, the state of awards shows in today's world, and why they continue to be...

Was a bestselling romantasy novel stolen from someone else's unpublished book? New Yorker staff writer Katy Waldman investigates a fascinating case of alleged plagiarism rocking the publishing world—the first novel copyright infringement to reach trial in a century. The case raises profound questions about creative ownership in publishing, while exposing the way books in this red-hot genre are wri...

Stuck in a creative rut? Need some fresh ideas? The solution isn't staring harder at your screen – it's getting up from your desk and walking. This simple activity has been the secret weapon of history's most brilliant minds, from Charles Dickens to Virginia Woolf, Aristotle to Steve Jobs. Science backs this up: walking increases creative output by 60% compared to doom scrolling. But not all walks...

The devastating wildfires in Los Angeles have destroyed 12,000 structures and taken at least 25 lives. In an intimate conversation, guest Lee Ann Daly shares her harrowing experience of evacuating her Pacific Palisades home with just minutes to spare, managing to save three cats and only a few documents. Lee Ann is a creative executive and former head of marketing at ESPN, Reuters, and the Game Sh...

Two years ago, most people had never heard of generative AI tools like ChatGPT or Claude. Now, they're an integral part of our workflow. But what astonishes and impresses us about the technology also scares the living bejesus out of us. Will AI eventually replace us as writers? Will our profession become obsolete? How do we make this rapidly evolving technology our assistant, not our adversary? Te...