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 with topics and answers, and how their own dating lives bled into the columns in real time. They also reflect on the twilight years of print magazines and the lessons learned navigating freelance careers as the industry shrank.

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, which chronicles how she transformed experiences she thought defined her shame into a writing career built on radical honesty. In our juicy conversation we talk about: Witnessing the exploitation tactics on the Girls Gone Wild bus  Raising over $32,000 for Black Lives Matter by offering topless photos to donors How you can be an exhibitionist but not an extrovert Writing dick reviews on OnlyFans as a creative writing exercise The difference between sexploitation and empowerment when it comes to monetizing your looks

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 nomintations for the best rappers of this time.  For more content like this, subscribe to Small Talk  Wanna go to Gen X Con? Sign up 

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 survivor before Me Too became a movement, and why she returned to Yale at 65 only to discover she reads in the 17th percentile.  TIMELINE: 00:35 Being canceled before it was a thing 01:47 The New York Times Magazine cover story at 18 03:29 JD Salinger's letter and the beginning of their relationship 04:30 Moving in with Salinger and giving up Yale 05:39 Keeping the secret for 25 years 06:22 Writing "At Home in the World" and the backlash 08:26 When 18-year-olds dating 53-year-olds was "romantic" 09:41 The Charlie Rose interview (and what happened after) 10:27 Why the culture turned against her in 1998 11:23 Can you separate the artist from the art? 13:25 Teaching memoir to women in Guatemala 15:45 Writing family sagas and "How the Light Gets In" 16:31 Growing up in a problematic family 17:00 Mother's writing bootcamp from age 3 22:23 Including real-world events (Trump, January 6th) in fiction 24:09 Writing is not therapy or catharsis 29:43 Throwing away manuscripts that aren't good enough 30:08 Discovering ADHD at Yale at age 65 32:08 The D-minus French exam that changed everything 34:22 Reading in the 17th percentile 36:39 The gift of ADHD 40:39 "You cannot be a writer if you're not a reader" - and why that's wrong 41:48 Character-first vs. plot-first writing 43:33 Never knowing where the story will end (vs. John Irving) 44:18 No outlines - "outline is for a term paper" 46:22 Finding inspiration in news headlines 47:49 Why some stories are memoir and others are fiction 50:48 On sensitivity readers and the transgender character 51:44 When characters display "politically incorrect" attitudes 52:57 Fear of cancellation from the left 53:29 Trigger warnings at Yale and the softening of everything

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 storytelling than plot twists or spectacle. We also talk about writing restraint, trusting viewers, and building a world that feels strange but uncomfortably familiar.  Subscribe to my newsletter @jonsmalltalk.substack.com