Gen X Crisis with Robert Guess

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 midlifeI 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.

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 IrelandIt’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.

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.

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.

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.

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.

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.

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.

How do you redesign a life at 50 - agile and without regret?In this episode, Robert talks with technologist and agile coach Reggie Valentine, whose career spans reinsurance, dot-com media, and fintech. Reggie shares how discovering Agile changed not just his projects but his approach to life: prioritize, time-box, learn fast, and pivot without remorse.Robert and Reggie discuss 70-hour workweeks, a year “retired” in Belize, and why being “The Wolf” who fixes a mess beats chasing prestigious titles. Reggie reflects on AI as a time dividend, the wisdom of finishing over starting, and why experiences matter more than things.This one’s about dropping old backlogs, re-prioritizing your life, and keeping curiosity alive in midlife.Visit genxcrisis.com to subscribe to the Substack and get updates. Hosted on Acast. See acast.com/privacy for more information.

What does it mean to come of age as a “forgotten generation” - and carry those lessons into midlife?In this episode of Gen X Crisis, Robert talks with Liz LaPoint, writer and creator of GenXcellent on Substack, where she explores the culture and psychology of Generation X. Liz shares how growing up “free range” in the suburbs of Minneapolis shaped her independence, why Gen Xers often became late bloomers, and how our reluctance to self-promote has made us both resilient and overlooked.Robert and Liz dig into the traits that define Gen X - skepticism, empathy, and a tendency to do things alone, while comparing notes on parenting today versus the hands-off approach of the 70s and 80s. They explore sex, relationships, reinvention, and what it means to balance authenticity with the uncomfortable need for self-promotion in a digital world.This one’s about being seen, questioning old narratives, and recognizing how much of who we are comes from the way we were raised - and what we choose to unlearn.Visit www.genxcrisis.com to subscribe to Robert’s Substack and get exclusive updates.And follow Liz LaPoint on her Substack GenXcellent here: https://genxcellent.substack.com/ Hosted on Acast. See acast.com/privacy for more information.

What if the only path to a purposeful life is working through your personal trauma?Rob sits down with writer and Gen Xy co-host Lawrence Winnerman to unpack how childhood loss, identity, and reinvention can become a path, not a detour, to meaning. Lawrence shares the profound moments that shaped him: losing his father at 14, quietly coming out in a world that wasn’t ready, a night of despair that sparked a spiritual pivot, and the cross-country leap that led to early days at Amazon and a decades-long technology career.Together they explore Lawrence’s thesis that Gen X are late bloomers - resilient, skeptical, and finally ready to step into their power. They dig into ageism, the whiplash of AI-era change, why processing our own wounds is a necessity (so we don’t pass them on), and how stability, community, and even detachment can become conscious practices in midlife.If you’ve ever wondered whether trauma has a purpose, this episode is for you.Content note: This episode includes candid discussion of grief, suicidal ideation, and sexual abuse.Visit www.genxcrisis.com to subscribe to Robert’s Substack and get exclusive updates.And check out GenXy and 'The Daily Whatever' show hosted by Lawrence Winnerman and Dana Dubois.Lawrence can also be found on Substack here: https://substack.com/@lwinner Hosted on Acast. See acast.com/privacy for more information.

What happens when you leave your roots behind as a kid—and spend midlife searching for where you truly belong?In this episode of Gen X Crisis, Rob and his childhood friend George reflect on their parallel paths: Rob moving to Florida at 11, George to California at 13. Both left behind the tight community of Livingston, New Jersey, and both have carried that sense of dislocation into adulthood.George shares how trombone and music carried him to CalArts, how a chance opportunity pulled him into comics, and how he rode the wave of digital transformation in television animation for legendary studios like Hanna-Barbera and Imagineering. Along the way, he’s navigated ADHD, health challenges that led to losing 120 pounds, and the constant need to adapt as technology reshaped creative industries.They talk about loss, reinvention, and the ongoing search for connection - how empathy can feel like both a gift and a burden, and how midlife forces us to look for new ways to ground ourselves when the old maps no longer apply.This one’s about shared roots, resilience, and redefining belonging in a world that keeps moving.Visit www.genxcrisis.com to subscribe to Robert’s Substack and get exclusive updates. Hosted on Acast. See acast.com/privacy for more information.

What does a life spent managing global fragility teach us about navigating our own in midlife?In this episode of Gen X Crisis, Rob chats with his friend Jens Hesemann, a longtime international development leader whose 20+ years with the United Nations took him around the world, responding to refugee displacement and humanitarian crises. Jens shares what impact really looks like on the ground, how constant moves shape family life, and why midlife has him rethinking balance and resilience.Rob and Jens talk about the mental weight of living in a fragile world, how aging and recovery change the way we show up, and the parallels between managing crisis at scale and managing the personal transitions of midlife. Jens also looks ahead to innovation, from market-based solutions to the role of AI in crisis response - while staying rooted in the human side of the work.This one’s about service, sacrifice, and what we can learn about redesigning the second half of life from someone who has spent his career helping others hold steady in the storm.Visit www.genxcrisis.com to subscribe to Robert’s Substack and get exclusive updates. Hosted on Acast. See acast.com/privacy for more information.

What if midlife isn’t about decline—but about rediscovering your strength, voice, and identity in ways you never imagined?In this episode of Gen X Crisis, Robert reconnects with Shari Ciapka, a old friend he hasn’t spoken to since 1986, who has spent the past several years reinventing herself in remarkable ways. Shari’s journey takes her from a traditional path in accounting and corporate leadership to becoming a competitive fitness athlete, fitness model, Spartan racer, and even a late-blooming singer finding her voice on stage.Robert and Shari talk about growing up in suburban New Jersey, parental expectations, and the “safe” choices that shaped early careers—before diving into how unexpected pivots, personal challenges, and a job elimination sparked Shari’s rebirth in midlife. They explore the mindset shifts that come with extreme fitness, the discipline of showing up, the courage to compete, and how physical strength fuels mental resilience. Shari also opens up about parenting two sons who’ve carved their own unconventional paths, the lessons of 9/11, her work in diversity and inclusion, and why she now sees herself as a maximizer helping others unlock their potential.This one’s about rediscovering possibility at any age, shedding self-imposed limits, and embracing reinvention as a lifelong practice.Visit www.genxcrisis.com to subscribe to Robert’s Substack and get exclusive updates.And follow Shari Ciapka here: Facebook / Instagram / LinkedIn / 1stPhorm Hosted on Acast. See acast.com/privacy for more information.

What if midlife isn’t about winding down—but about redefining relevance in a world that won’t stop moving?In this episode of Gen X Crisis, Robert sits down with Suzanne Lindbergh, a longtime marketing leader whose 23-year career at Apple helped shape modern influencer marketing. Suzanne shares her journey from dreaming of investigative journalism to finding herself at the center of Apple’s culture—working through the Think Different era, reporting directly to Steve Jobs, building its entertainment marketing team, and pioneering product placement strategies that would ripple across the industry.Robert and Suzanne talk about the mental disorientation of aging in a culture obsessed with youth, what it’s like to feel both current and overlooked, and how Gen Xers are navigating work, parenting, and identity in middle age. They dive into her experiences at Apple, AOL/Verizon’s Build Studio, and Uber, the evolution of social media and the influencer economy, and what it means to stay culturally relevant while raising kids who are themselves cultural translators.This one’s about staying present, questioning what “being done” really means, and holding onto curiosity as a way of staying alive in midlife.Visit www.genxcrisis.com to subscribe to Robert’s Substack and get exclusive updates. Hosted on Acast. See acast.com/privacy for more information.

What if chasing the dream isn’t the point—and the real win is still loving creating music decades later?In this episode of Gen X Crisis, Robert talks with Jim Gerdeman, an old friend whose life has been shaped by a lifelong devotion to making music. Jim shares the arc of growing up in Cleveland, discovering music as a lifeline, and building a life in Boston as an active musician with The I Want You.Rob and Jim talk about the shift from wanting to be a rock star to creating purely for the joy of it, how the music scene has changed from the analog days to AI and algorithms, and the way middle age reframes ambition. There’s also nostalgia for early high school and college bands, cassette tapes, and the unique magic of playing in a room with other musicians.This one’s about holding onto what you love, no matter where the mainstream is headed.Visit www.genxcrisis.com to subscribe to Robert’s Substack and get exclusive updates.And check out Jim Gerdeman's entire catalog at https://jimgerdeman.bandcamp.com/ and Jim's new vinyl album Mystery Rhyme coming this Fall 2025. Hosted on Acast. See acast.com/privacy for more information.

What if midlife isn't about resting on your laurels—but redefining what success truly means?In this episode of Gen X Crisis, Robert sits down with Ken Gelman, a lifelong friend he met on a teenage bus tour across the United States to reflect on music, parenting, sports, and the surreal experience of turning 55. Ken, a veteran sports executive whose career has included executive roles in the NHL and WWE, and working on projects for the NFL and numerous sports leagues, shares the twists and turns of building a meaningful career while staying grounded in family, passion, and purpose. Together, they talk about parenting young adults, navigating ambition at midlife, and how growing older changes what we value—and how we define success.There’s talk of Metallica and Motorhead, 80s spring break memories, the rise of MMA and AI, and the simple joy of climbing a mountain to remind yourself you're still alive.This one’s about friendship, reflection, and the beauty of still being in the game.Visit www.genxcrisis.com to subscribe to Robert’s Substack and get exclusive updates. Hosted on Acast. See acast.com/privacy for more information.

What’s essential at 55? Maybe it’s not slowing down—it’s going deeper.In this episode of Gen X Crisis, Robert reconnects with John Minutaglio, a lifelong friend whose passions, quirks, and obsessions have only intensified with age. It’s an unforgettable conversation that ranges from Rickenbacker guitars and rare astrological data sets to parenting philosophies and the underrated art creating your own rules..John, a technology executive, guitar collector, and astrology app creator, shares what drives him to go deep. He’s not interested in slowing down, and he makes a compelling case for why none of us should either.As they reflect on nearly four decades of friendship, Rob and John revisit the wisdom ritual they began in their twenties—where John, older by six days, offers annual guidance. The episode moves through stories of 1980s Florida, musical awakenings,, AI optimism, and why being unstoppable might just be a Gen X superpower.This one’s about memory, identity, creativity—and how midlife might actually be the best time to start something new.Visit www.genxcrisis.com to subscribe to Robert’s Substack and get exclusive updates. Hosted on Acast. See acast.com/privacy for more information.

What does it mean to live an examined life—and make peace with the version of yourself you became?In this episode of Gen X Crisis, Robert reconnects with Paul Westcott, a childhood friend from early 1980s Livingston, New Jersey. After reuniting a few years ago, the two sit down for the kind of honest, searching conversation that only decades of living can make possible.What begins with memories of the cultural ripple effect of Paul’s family moving from London to suburban New Jersey becomes something deeper—a reflection on identity, creativity, aging, and what it takes to keep going when the path doesn't unfold as planned.Paul, a former professional songwriter and now entrepreneur, shares his journey navigating heartbreak, artistic ambition, and personal reinvention. From the dislocation of moving between countries as a kid to wrestling with the emotional weight of midlife, he speaks with humor and vulnerability on examining life from the inside.It’s a raw, funny, and powerful conversation about being Gen X—how we carry the dreams of who we were, who we thought we’d be, and who we’re still becoming.Visit www.genxcrisis.com to subscribe to Robert’s Substack and get exclusive updates. Hosted on Acast. See acast.com/privacy for more information.

What if all it took to change your life was one honest step in a new direction?In this episode of Gen X Crisis, Robert reconnects with Lainie Reisman, a childhood friend he hasn’t spoken to in nearly 40 years. What starts as a trip down memory lane—tracing their shared summers at a beloved (and now very politically incorrect) New Jersey summer camp—quickly opens into a deeper conversation about growth, identity, and what it means to reinvent yourself in midlife.Now an international development expert, hiking guide, and self-described rebirth enthusiast, Lainie reflects on everything from her early years at the University of Pennsylvania to ditching the prestige track for a life of global impact. She opens up about raising kids in a changing world, letting go of old definitions of success, and why midlife has been the most creative, expansive time of her life.It’s a funny, honest, and inspiring conversation about nostalgia, purpose, and the freedom that can come when you stop trying to live someone else’s version of success. If you’ve ever looked at your life and asked, “Is this really what I want?” - this one’s for you.Visit www.genxcrisis.com to subscribe to Robert’s Substack and get exclusive updates. Hosted on Acast. See acast.com/privacy for more information.