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.

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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.

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Jonathan Small

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.

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Jenny Mag

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.

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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.

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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.

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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.

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This episode is sponsored by AG1.

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.

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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

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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.

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