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On the show
Recent episodes
How This Writer Found Freedom in a Tell-All Memoir
Mar 26, 2026
Unknown duration
A Hip Hop Historian on the Records That Started It All
Mar 2, 2026
Unknown duration
Joyce Maynard on J.D. Salinger, Survival, and Writing Through ADHD
Jan 25, 2026
Unknown duration
Inside the Pluribus Writers' Room
Jan 2, 2026
Unknown duration
The Money Conversation Writers Can No Longer Avoid
Dec 2, 2025
Unknown duration
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| Date | Episode | Description | Length | ||||||
|---|---|---|---|---|---|---|---|---|---|
| 3/26/26 | How This Writer Found Freedom in a Tell-All Memoir | 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 | — | ||||||
| 3/2/26 | A Hip Hop Historian on the Records That Started It All | 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 | — | ||||||
| 1/25/26 | Joyce Maynard on J.D. Salinger, Survival, and Writing Through ADHD | 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 | — | ||||||
| 1/2/26 | Inside the Pluribus Writers' Room | 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 | — | ||||||
| 12/2/25 | The Money Conversation Writers Can No Longer Avoid | 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 to Securing Your Financial Future, break down how our generation ended up here and offer practical steps we can take now to build a future that feels possible, not panicked. Even if you're not Gen X, there is practical and useful advice for you here. Subscribe to my Small Talk substack for more conversation like this | — | ||||||
| 11/24/25 | 3 Keys to Building a Seven-Figure Writing Business | 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. Follow us on Substack: Amy Suto Jonathan Small | — | ||||||
| 11/17/25 | The Magazine Traditional Media Refuses to Make | 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 relationships Gen X women have with their Boomer mothers, what it's like running a magazine on nights and weekends with zero budget, and why owning your platform matters when you've been disposable to corporate publishers one too many times. Lili also opens up about empty nesting with twins, being back in the dating world after 25 years of marriage, and creating content that makes readers say "I thought it was just me." This episode originally aired on my new podcast Small Talk. Subscribe to Small Talk Podcast Small Talk Substack Jenny Mag | — | ||||||
| 11/11/25 | Elizabeth George: Inside the Mind of a Master Crime Writer | 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@substack.com Try AG1 and get a FREE bottle of Vitamin D3K2 AND 5 free AG1 Travel Packs with your first purchase @ drinkAG1.com/writeaboutnow | — | ||||||
| 9/3/25 | Why Teens Are More Unhappy Than Ever | 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 professor of psychology at San Diego State University, the author 10 Rules for Raising Kids in a High-Tech World. In this books she gives parents some really useful suggestions roadmap for helping their children deal with this epidemic. Jean talks about how the culture around childhood has shifted since the rise of smartphones, and what concrete steps parents can take right now to raise healthier, happier, more independent kids. Order AG1 @ drinkag1.com/writeaboutnow Subscribe to my Substack@ jonsmalltalk.substack.com | — | ||||||
| 8/19/25 | Kaila Yu on the Cost of Asian Fetishization | 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 her story and challenging the stereotypes that still harm Asian women today. Subscribe to my Substack: jonsmalltalk@substack.com | — | ||||||
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| 7/15/25 | The Truth Behind One of History's Most Misunderstood Men | 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 captain to pirate-hunter, the murky politics of the time, his dramatic trial in London, and the love story that's rarely told. Marquis argues Kidd was less Blackbeard and more fall guy — a man caught in a scandalous power struggle between the English crown, shady investors, and the East India Company. Subscribe to Jon's Substack Small Talk This episode is sponsored by AG1. | — | ||||||
| 6/26/25 | A Sassy Conversation with Magazine Icon Jane Pratt | 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 70% of newsstands after a boycott by the religious right The secret behind Sassy's success and why it changed so many lives Her evolution from Sassy to Jane Working with Michael Stipe, who she dated for years and now calls her best friend and daughter's godfather Her decision to launch Another Jane Pratt Thing on Substack rather than a standalone website How she finds new writers and spots a good story What makes her such a good editor Gen X resilience Why she hates the word "influencer," even though she was one of the first Her optimism about the current state of the media Name dropping The shift to multi-hyphenate careers, and what she puts as her profession on doctor's forms. Subscribe to Small Talk to hear more Substack Live interviews with interesting folk. | — | ||||||
| 6/11/25 | Captain Cook Reached Paradise. Then It Turned on Him. | 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 @ JonSmallTalk | — | ||||||
| 5/27/25 | What Every Author Gets Wrong About Publicity | 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 publishing a book — or even thinking about it — this conversation will help you understand the industry, the stakes, and what it takes to break through. Subscribe to my Substack: JonSmallTalk.substack.com Order AG1: DrinkAG1.com/writeaboutnow | — | ||||||
| 5/13/25 | The New Retirement Is Not At All What We Expected | 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, I had a live conversation with Brian Clark—entrepreneur, writer, and founder of Further—about what this next chapter actually looks like for Gen X. And how we can stop chasing old myths and start building something more sustainable and sane. For more content like this, follow me over @ jonsmalltalk.subtack.com Get a discount on AG1 @ drinkag1/writeaboutnow.com | — | ||||||
| 5/5/25 | The Advice We'd Give to Our Younger Selves | 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 daughters, and why small, well-phrased truths often carry the biggest impact. Other topics: – Why she made the leap from clerking at the Supreme Court to writing about happiness – The Four Tendencies framework and why so many of us are "Obligers" – Her process for crafting sticky, memorable aphorisms – Why motivation doesn't work as a motivation tool Subscribe to my Substack @ https://jonsmalltalk.substack.com/ This show is sponsored by AG1. Sign up for a $76 discount @ DrinkAG1.com/writeaboutnow | — | ||||||
| 4/8/25 | The NYT called Gen X Obsolete. That Didn't Go Well. | 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 X-er, writer, alt-rock aficionado—joins the show to talk about why the article sparked so much rage, what it got dead wrong, and how Gen X is not just surviving but reinventing midlife on their own terms. Read Jon's response on Substack here. Read the original NYT story here. All things Dana DuBois can be found here. | — | ||||||
| 3/20/25 | 5 Secrets for Crafting an Unforgettable Memoir | 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 for constructing your memoir from the ground up. On this episode, we talk about useless writing advice such as just write a first draft, why the journey is more important than the memories themselves, and the things to prep yourself for capturing your life on the page in the best way possible. Write About Now is sponsored by AG1, order using my code and get some freebies.DrinkAG1.com/writeaboutnow Subscribe to the Small Talk substack @ https://jonsmalltalk.substack.com/ | — | ||||||
| 3/4/25 | Kenneth Turan on the Hollywood Duo Who Built an Empire | 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 their eventual fall. | — | ||||||
| 2/25/25 | 2025 Oscars: Scandals and Predictions | 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 popular despite yearly reports of their demise. Katey also delves into the scandals clouding this year's Oscar race and shares her expert predictions for best picture, best actress, best actor, and more. | — | ||||||
| 2/12/25 | An Explosive Lawsuit Reveals the Dark Secret of Romantasy Novels | 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 written. You'll never look at enemies-to-lovers werewolf sexcapades the same way again. Read Katy's story @ https://bit.ly/4hyxLUP Subscribe to Small Talk @ jonsmalltalk.substack.com | — | ||||||
| 1/30/25 | Walk This Way | 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 are created equal. Award-winning author Abbs Streets shares insights from her book "52 Ways to Walk," breaking down exactly when, where, and how to walk for maximum creative benefit. | — | ||||||
| 1/16/25 | An LA Wildfire Survivor Shares Her Story | 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 Show Network. In our conversation, she brings her unique perspective to processing tragedy. We discuss the true character of the Pacific Palisades that you won't hear in the news, details of her traumatic escape, the challenges of navigating California's complex fire insurance system, and how she's coping with the uncertainty of this unprecedented tragedy. To donate to families affected by the fire: Mutual Aid Los Angeles Network To help animals in need: Pasadena Humane Society | — | ||||||
| 1/2/25 | The Best Ways to Use AI Writing Tools | 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? Tech expert Christoper S. Penn joins the show to demystify the technology and offer tips on making AI a productive collaborative partner. Topics include understanding how generative AI works, writing effective prompts using his RAPPEL framework, comparing top AI tools like ChatGPT, Claude, and Gemini, tackling thorny ethical questions, and practical strategies for using AI in your work. Whether you're excited or anxious about AI's impact on your profession, this episode gives you a roadmap to embracing the technology's awesome power. Follow us at: Small Talk substack: https://jonsmalltalk.substack.com/ Christoper S Penn's Almost Timely Newsletter: https://almosttimely.substack.com/ | — | ||||||
| 12/27/24 | Write About Now: The Best of 2024 | In this year-end episode, we look back at some of the most memorable moments from the show, featuring intimate discussions with some of the literary world's most fascinating voices. You'll hear the writing origin stories of JA Jance, Joyce Maynard, and Richard Osman, how Kristin Hannah overcomes her fear of failure, writing through writer's block with Steve Almond, the best writing advice linguist Valerie Fridland ever received, Todd Boyd on the global appeal of hip hop, and how Molly Roden Winter endured 50 rejections of her manuscript before getting a yes. To listen to the interviews in full, click the links below. JA Jance Joyce Maynard Kristin Hannah Richard Osman Steve Almond Valerie Fridland Todd Boyd Molly Roden Winter Support the show by subscribing to the Small Talk substack @ https://jonsmalltalk.substack.com/ | — | ||||||
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