Small Talk: A Gen X Podcast

For much of the 1990s and early 2000s, I was tapped by women's magazines to explain what guys think and why they do the things they do. I wasn't alone. There's a small fraternity who share this odd magazine DNA — men who got paid, often under fake names, to translate men for an audience of women. I caught up with two of them, Ky Henderson (my editor and successor as the Guy Guru at Cosmo) and Andrew Postman (another Jake at Glamour), to talk about whether those reader questions were actually real, the topics editors wouldn't let us touch, and whether we have any regrets about the advice we gave lovelorn Gen Xers and Millennials.

Many midlife Americans fantasize about living abroad—especially when the Orange Monster dominates our thoughts and our country seems to be going the way of the Handmaid's Tale. But what does it actually take to uproot your life and make the leap? To help us unpack the realities of expat life, I spoke to Sacha Cohen, a Gen X writer, journalist, and former public relations executive who recently traded the Beltway for the Belle Époque. After years of dreaming blue, white, and red, Sacha and her husband finally made the move earlier this year, embracing la bonne vie with both eyes open. Sacha writes A Good Vintage, a Substack exploring midlife reinvention and l'art de vivre. She's an animal lover (currently pet-less but planning for a French poodle), a Francophile, and someone who's learning what it really means to start over in your late 50s. We talked about: The backstory of her move—how years of annual trips to France turned into test-runs in Bordeaux, Rouen, and Dijon before the final decision What the French get right: quality of life, work-life balance, prioritizing family and friends, socialist values, healthcare, seasonal food. What the French get wrong: toilet paper quality, no dryers The challenges Americans don't expect from explaining yourself at the gym to buying sheets and towels The truth about making a living in France, ageism without language barriers, and the reality that moving doesn't magically transform you Why she loves having no history in Paris—the freedom to reinvent yourself with every new person you meet Practical advice for anyone considering the leap: dip your toes in slowly, research relentlessly, learn the language, build community, and be emotionally resilient Sacha Cohen!

Career coach Colleen Paulson (founder of Ageless Careers, 100K LinkedIn followers) breaks down the brutal reality facing Gen X job seekers — and what we can do about it. The average search now takes 12-18 months. Portfolio careers aren't optional anymore. Smaller companies are hiring 50x faster than corporations. And our Gen X humility is killing us on LinkedIn. Sobering, frustrating, but ultimately empowering conversation about navigating work in 2026.

The 90s usually get called hip hop's golden era. But the foundation was crafted in the 80s. I went live with journalist and cultural critic Jeff Chang, author of Can't Stop Won't Stop, to talk about the records that changed the game — from Blondie's "Rapture" to It Takes a Nation of Millions to Hold Us Back, from Run-DMC to Eric B. & Rakim. Then we talk about the greatest Gen X rappers of all time. Jeff drops some science here. Straight from the dome. I thought I knew everything there was to know about 80s hip hop. Man, was I wrong. For more content like this, sign up to the Small Talk Substack Wanna go to Gen X Con? Find out more here. 

MTV was the center of the pop cultural universe in the '80s and '90s. Then, just like that, it wasn't. Dave Holmes had a front-row seat to both the meteoric rise and shocking fall of the network that defined Gen X. As an MTV VJ from 1998 to 2003, Holmes hosted iconic shows like "TRL" and "120 Minutes," interviewing everyone from Tom Cruise to Joe Strummer during the channel's peak years. But Dave also witnessed the critical mistakes that killed the video star—and they weren't what most people think. While many blame reality TV or changing viewer habits for MTV's decline, Holmes points to a corporate decision that sealed the network's fate. Today, Dave has successfully reinvented himself as editor-at-large for Esquire and producer and host of the popular podcast series Who Killed the Video Star? and Waiting for Impact. Dave is living proof that career pivots are possible even when entire industries collapse. In this interview, we talk about: Being a closeted gay teenager in a conservative Catholic family in 1980s St. Louis His first memories of MTV and how it changed the way he saw the world. Dreaming of being an MTV VJ while DJing at a tiny local radio station as a 15-year-old. The 4 AM decision to audition for MTV's "Wanna Be a VJ" contest despite his inner voice saying "you're too old" at 27 Losing to Jesse Camp but parlaying runner-up status into hosting TRL and 120 Minutes and more. Why MTV isn't what it was Reinventing himself from TV host to magazine editor and podcast producer.   Subscribe to: jonsmalltalk.substack.com for more Gen X content. 

Andy Buckley never expected to become David Wallace, one of television's most recognizable bosses. But a chance encounter at a farmer's market changed everything. In this Small Talk conversation, the Gen X actor tells the story of his surprising second act from a financial advisor in corporate America to CFO of Dunder Mifflin on The Office. He also shares stories from the set working with Steve Carrell, Jenna Fischer, and Melora Hardin, why The Office continues to be so popular decades after it stopped production, particularly with Gen Z, and the current state of Hollywood production for 50-plus actors. Subscribe to Small Talk for more great Gen X content!

Alison Tatlock, executive producer and writer on the hit TV show Pluribus, breaks down why the show resonates so strongly, especially with Gen X viewers raised to question authority, resist groupthink, and trust their own instincts.  We talk about: Why Pluribus sparks debate instead of offering answers How Gen X distrust shapes the show's central character The fear of being left behind by "progress" Grief as a quiet engine of the story Happiness as something imposed, not chosen Why belonging can feel like a threat The comfort and danger of consensus What refusing the hive actually costs For more content like this, subsribe to jonsmalltalk.substack.com Watch the full interview on YouTube

Here's a shocking revelation: You know Norm and Cliff from Cheers? They were 37 and 38 years old at the height of that show's popularity. The old dudes in Cocoon were in their 40s! Why did men look so much older back in the day? Investigative reporter Steven Greenstreet, host of the Make This Make Sense at the New York Post, joins the show to explain why men from earlier generations aged so differently. Steven also debunks the latest UFO myths and shares his Gen X obessions, from The X-Files to Radiohead.

Author Max Brooks grew up surrounded by Hollywood royalty, but he never felt like he fit the part. Before World War Z and before he advised the U.S. military on disaster planning, he was the child of Mel Brooks and Anne Bancroft, who obsessed over niche interests and tried to survive school one awkward lunch at a time. In this episode, Max explains why being an outsider became his greatest advantage, how Gen X turned nerd culture into a superpower, and what happens when you finally stop pretending to be someone else. We talk zombies, obsessive research, and the strange freedom that comes from not caring whether anyone thinks you're cool. Max shares the long road from dismissed ideas to global influence. If you've ever felt different, this conversation hits home. Watch the entire interview @ jonsmalltalk.substack.com More on Max Brooks

More than three in five Gen Xers are not confident in their ability to achieve a dream retirement and nearly half think they'll outlive their savings. We have far less confidence in our futures than generations before us. Kerry Hannon and Janna Herron, co-authors of Retirement Bites: A Gen X Guide to Securing Your Financial Future, explain how we got here and what we can do about it. They offer some useful, realistic tips about how to retire happily, even if it might not happen as soon as you'd like, including: How to build meaning and purpose into the second half of life. The mindset traps that keep us stuck, and how to break them. Reasonable retirement numbers for a typical Gen Xer. Biggest money leaks Gen Xers make. What a realistic reinvention timeline looks like Understanding Social Security, retirement accounts, and healthcare. Getting out of credit card debt. Subscribe to Small Talk for more Gen X content!

Former Hollywood TV writer Amy Suto walked away from her dream job to build a seven-figure writing business. She has a new book out called Write for Money and Power: The Anti-Starving Artist's Guide to Becoming a Seven-Figure Writer, which argues that writers need to stop romanticizing poverty and start building sustainable businesses. In this conversation, she reveals the three pillars creatives should focus on if they want to make money. Topics include: why self-publishing beats traditional deals, how she made $300K on Upwork, the Substack tweaks that added $100K in value, where freelance writers actually make money in 2025, why cold emails still work, and how to stop romanticizing the starving artist myth. This interview is packed with actionable strategies you can use today. Small Talk Amy Suto  

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."  Subscribe to Small Talk Podcast Small Talk Substack Jenny Mag

One minute you're helicoptering your kid to games and recitals, nagging them about their messy room. Then they're gone. An empty bedroom. An empty chair at the dinner table. You know this is a healthy part of their development, but it still feels like a piece of your own life just vanished. Some feel sadness. Some feel empty. Some even feel relief. But nobody really tells you how to navigate this. So I asked Larry Cornett to come on Small Talk. Larry is a former Silicon Valley exec with a PhD in psychology who spent decades at places like Apple, Yahoo, and eBay. Now he helps people reinvent at midlife. This episode digs into what empty nesting does to us emotionally, how to stay close to your adult kids without smothering them, and how to rebuild your identity in this new phase. [email protected] https://larrycornett.coach/