Gen X Crisis with Robert Guess

Robert Guess
  • 3.9 (7)
  • SOCIETY & CULTURE
  • UPDATED WEEKLY

Gen X Crisis is a podcast about hitting your 50s and realizing you’re still trying to make sense of it all - career, identity, aging, purpose, and how we got here. And more importantly, where do we go from here? Hosted by Robert Guess, each episode features raw, honest, and often funny conversations with old friends, thinkers, and fellow GenXers navigating the complexities of midlife. From the exhaustion that follows decades of grinding to the disorientation of a world that feels increasingly unrecognizable, we explore what it means to slow down, redefine ambition, and find meaning in the chaos. We talk about aging, reinvention, the weirdness of midlife, and what it means to slow down, show up, and keep going when the world looks nothing like the one we grew up in. New episodes every week. Learn more or sign up at www.genxcrisis.com to get updates via Substack. Hosted on Acast. See acast.com/privacy for more information.

  1. 11/25/2025

    Crisis Averted w/Robert Guess (Season 1 Finale)

    What happens when you spend almost year digging into your past through conversations with GenXers about aging, purpose, identity, and the strangeness of midlife? If you’re me, you find a path to curing your own midlife crisis. In this short Season 1 finale, I share what creating Gen X Crisis has actually done to me - how a podcast I started in Paris at 54, in the thick of disorientation and loneliness, became the very thing that pulled me out of it. I talk about reconnecting with old friends I hadn’t spoken to in decades, the surprising emotional depth of those conversations, and the recurring reminder (mostly from the women!) that maybe this isn’t a crisis at all… maybe it’s a reinvention. I reflect on the big themes that emerged across the season: • The psychedelic trip of being in your 50s in a world you barely recognize • The trap of nostalgia and how quickly you can start feeling old • The Gen X playbook we inherited - especially around not self-promoting, keeping your head down, and how that shapes our lives today • The physical side of aging, and how much it impacts our mental state • The power of staying connected when your instinct is to isolate • Why reinvention is not optional - and might actually be the best part of midlife I also share what I learned from hosting my first Gen Z guest, my stepson Felix, and why Season 2 will expand beyond Gen X, bringing in Gen Z, Millennials, and Boomers to round out the conversation. This finale is a thank you, a reset, and a look forward. I talk about the guests who changed me, the friendships I wish I’d kept up, the community I want to build (especially for Gen X men who struggle to talk about this stuff), and why I’m more hopeful now than I’ve been in years. Season 1 was about getting out of my crisis. Season 2 is about what comes next. Thanks for being part of this. See you in January. Visit www.genxcrisis.com to subscribe and get updates on Season 2. Hosted on Acast. See acast.com/privacy for more information.

    9 min

  2. 11/18/2025

    Gen Maxxing w/Felix McCormick

    In this week’s episode of Gen X Crisis, Robert expands the generational boundaries with his first non-Gen X guest, Felix McCormick, a Gen Z philosophy major at The University of Galway. Robert has known Felix since he was seven years old. Now 22, Felix has been listening to the podcast and brings with his own unique and insightful take on Gen X and the world we’re leaving behind. This episode is part conversation, part reckoning, and part window into how Gen Z sees the future and Gen X. Robert and Felix talk about: • What Gen Z really thinks Gen X got righ and wrong • The collapse of the social contract how Gen Z is responsing • Why extremism and polarity is rising among young people • Meme culture, absurdity, and what’s actually funny now • How social media shapes identity and politics • Parenting (from both sides), agency, and the traps Gen X falls into • What gives Gen Z hope in a chaotic, accelerating world • The philosophy that guides him, and the life he’s building in Ireland It’s raw, honest, funny, and at times uncomfortable, in the best possible way. If the podcast has been about Gen X looking inward, this episode is about seeing ourselves through another generation's eyes. Visit www.genxcrisis.com to subscribe to Robert’s Substack and get exclusive updates. Hosted on Acast. See acast.com/privacy for more information.

    1h 23m

  3. 11/11/2025

    Embracing Uncertainty w/Jonathan Small

    What if uncertainty isn’t something to escape but the space where reinvention begins? In this episode of Gen X Crisis, Robert talks with journalist, podcaster, and Substack writer Jonathan Small, whose career spans the magazine heyday of the ’90s to today’s creator economy. From interviewing George Carlin as a temp to launching the hit podcast Write About Now, Jon’s story is about learning to adapt, create, and stay curious when the ground keeps shifting. Rob and Jon explore the emotional terrain of midlife, the unease of not knowing what’s next, the quiet ache of fading relevance, and the paradox of finding freedom when the plan falls apart. They dig into how work, identity, and creativity evolve with age, and why embracing uncertainty may be the most honest way to live right now. This one’s about letting go of control, trusting your instincts, and realizing that “not knowing” can be the start of something new. Visit www.genxcrisis.com to subscribe to Robert’s Substack and get exclusive updates. And check out Jonathan Small’s Substack, Small Talk, and his best selling book Write About Now, interviews with over 400 writers in journalism, fiction, non-fiction. Hosted on Acast. See acast.com/privacy for more information.

    1h 29m

  4. 11/04/2025

    Replaying Youth w/Rob Janicke

    What if reinvention means returning to the music that made you who you are? In this episode of Gen X Crisis, Rob talks with Rob Janicke, a writer and lifelong student of music whose book Slacker: 1991, Teen Spirit, Angst and the Generation That Created It explores the origins and legacy of the grunge movement. For Janicke, it’s also deeply personal: a love letter to the music that carried him through adolescence, self-doubt, and the messy process of finding his voice again in midlife. Recently published and optioned for a documentary, Slacker became more than a deep dive into music history, it marked a creative rebirth for Janicke, proving that passion and persistence can still change your life in your fifties. They reflect on how the spirit of the 90s - authentic, messy, and loud - still echoes in today’s search for identity, and how becoming a writer has given Janicke the chance to model something unexpected for his kids: that there’s no single path to purpose, and meaning can be remixed at any age. This one’s about the art of coming full circle - about replaying youth not to relive it, but to remind yourself, and those watching you, that the music never really stops. Visit www.genxcrisis.com to subscribe to Robert’s Substack and get exclusive updates. To buy Rob's book Slacker: 1991, Teen Spirit, Angst and the Generation That Created It, visit Rob's website at https://www.robjanicke.com/ Hosted on Acast. See acast.com/privacy for more information.

    1h 26m

  5. 10/28/2025

    Spinning Identity w/Marc Liepis

    What happens when your job becomes your identity - and then it’s gone? In this episode of Gen X Crisis, Robert talks with Marc Liepis, whose three-decade career took him from NBC publicity to producing late night with Jimmy Fallon and, most recently, Howard Stern. Marc opens up about the intoxicating highs of being at the center of pop culture - launching shows, prepping stars like Adam Sandler and Betty White, producing bits that became viral before “viral” existed - and the shock of reinvention when the lights dim. Robert and Marc dig into the grind and the thrill of late night, the mentorship that kept him going at SNL, and what it feels like to shift from PR to producing comedy that millions would see the next night. They also explore how the entertainment landscape has splintered, what’s been lost with the decline of monoculture, and why the “campfire” moments of Carson and Conan feel so rare today. Beyond the industry, Marc reflects on fatherhood, parenting an only child in New York, navigating conversations his own parents never would have had, and the universal midlife struggle to find inherent value outside of a job title. This one’s about reinvention, relevance, and reorienting when your life’s work no longer defines who you are. Visit www.genxcrisis.com to subscribe to Robert’s Substack and get exclusive updates. And visit Marc's Substack at https://truthpoop.substack.com/ Hosted on Acast. See acast.com/privacy for more information.

    1h 35m

  6. 10/21/2025

    Becoming Selfesque w/Joanna Baxter

    What if midlife is about redefining “selfish” as finally caring for yourself? In this episode of Gen X Crisis, Robert talks with writer Joanna Baxter for a conversation about resistance, recalibration, and midlife reinvention. From her roots in West Vancouver to crossing the Atlantic on a sailboat, Joanna shares how writing, letter-keeping, and slowing down became ways to record and reframe her life. They explore what it means to move from giving endlessly to everyone else toward claiming space for yourself—without apology. Joanna calls it becoming selfesque: caring for the self so you can show up with more clarity, honesty, and energy for others. Along the way, the two talk about generational shifts, parenting without a handbook, why Gen X might be the last analog generation, and how to recalibrate your life when everything feels like it’s speeding up. It’s a conversation about slowing down, listening harder, and learning to drop the act so you can live from a truer place. Visit www.genxcrisis.com to subscribe to Robert’s Substack and get exclusive updates. And check out Joanna Baxter's writing at https://www.joannabaxterwrites.ca/ Hosted on Acast. See acast.com/privacy for more information.

    1h 35m

  7. 10/14/2025

    Silent Rebellion w/Joanna Bissada

    What if midlife isn’t a crisis - but a chance to reprogram the algorithm that’s been running your whole life? In this episode of Gen X Crisis, Robert sits down with Joanna Bissada, a former corporate lawyer turned executive coach who has lived through profound personal and professional change. From growing up between cultures in Paris with Lebanese and Egyptian roots, to building a career in law and tech at Microsoft and Cisco, Joanna’s story is one of rebellion and compliance, always pushing against expectations while still carrying them. Joanna shares how divorce, empty nesting, and a string of accidents forced her to confront the programs she inherited—job + marriage = success - and rewrite them for herself. Robert and Joanna explore how silence became her truest teacher, why choosing your people is as important as choosing your career, and how transformation often feels like collapse before it feels like freedom. This one’s about breaking free of inherited scripts, listening for what’s beneath the noise, and embracing midlife as a time of radical reinvention. Visit www.genxcrisis.com to subscribe to Robert’s Substack and get exclusive updates. Hosted on Acast. See acast.com/privacy for more information.

    1h 10m

  8. 10/07/2025

    Bridging Community w/Greg Curtis

    What holds us together as life keeps changing? In this episode of Gen X Crisis, Rob reconnects with musician and recording engineer Greg Curtis, nearly two decades after Greg produced Robert's The Letter Green EP in his basement. From growing up in small-town Wisconsin to building The Bridge, one of LA’s top film and television scoring studios, Greg’s story is about how community shapes creativity, resilience, and meaning. Rob and Greg talk about the values we carry from childhood, the lessons of collaboration in music, and how technology - home recording, streaming, even AI - is reshaping what community looks like. They explore the balance between holding onto tradition and adapting to change, and how music at its best is always about people, not just sound. This one’s about basements and big stages, old friends and new collaborators and the reminder that community is what makes the work, and the life, matter. Visit www.genxcrisis.com to subscribe to Robert’s Substack and get exclusive updates. And check out Greg's latest project producing The Litteral Truth by acclaimed LA session player Paul Litteral. And here's a track from The Letter Green project that Greg and Rob worked on together in 2007. Hosted on Acast. See acast.com/privacy for more information.

    1h 26m
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Ratings & Reviews

3.9
out of 5
7 Ratings

About

Gen X Crisis is a podcast about hitting your 50s and realizing you’re still trying to make sense of it all - career, identity, aging, purpose, and how we got here. And more importantly, where do we go from here? Hosted by Robert Guess, each episode features raw, honest, and often funny conversations with old friends, thinkers, and fellow GenXers navigating the complexities of midlife. From the exhaustion that follows decades of grinding to the disorientation of a world that feels increasingly unrecognizable, we explore what it means to slow down, redefine ambition, and find meaning in the chaos. We talk about aging, reinvention, the weirdness of midlife, and what it means to slow down, show up, and keep going when the world looks nothing like the one we grew up in. New episodes every week. Learn more or sign up at www.genxcrisis.com to get updates via Substack. Hosted on Acast. See acast.com/privacy for more information.

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