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 disorientatio...

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 p...

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 a...

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 mus...

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 A...

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...

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 i...

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 commun...

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 wor...

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...

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...

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 adulth...

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 grou...

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...

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...

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...

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 th...

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 creati...

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 me...

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...

What if the hardest part of being an artist in midlife wasn’t the work—but finding time to do it at all? In this episode of  Gen X Crisis , Robert talks with Boston-based singer-songwriter and longtime Berklee College of Music voice faculty member Kristin Cifelli about evolving your creative voice in midlife. They trace Kristin’s journey from suburban New Jersey to Berklee, from early songwri...

What if you actually became the thing you dreamed of as a kid—and still found yourself wondering what comes next? In this episode of Gen X Crisis, Robert sits down with his oldest friend, former TV anchor Ed Greenberger, for a thoughtful, funny, and nostalgic conversation about ambition, aging, and reinvention. Robert and Ed talk about childhood dreams of sportscasting, a 25-year broadcasting care...

What if the thing you were meant to do was waiting for you all along—but it took a midlife detour to finally see it? In this episode of  Gen X Crisis , Robert reconnects with longtime friend and stand-up comic Robert Field for a funny, honest, and deeply relatable conversation about reinvention in your 50s. They talk about chasing creative dreams later in life, the odd comfort of driving 17,0...

What happens when you start telling your story—not to impress anyone, but to finally feel like yourself? In this episode of  Gen X Crisis , Robert reconnects with writer and cultural commentator Dana DuBois for a wide-ranging, emotionally honest conversation about identity, parenting, and what it means to come of age again in your 50s. Robert and Dana talk about writing as an act of survival,...

What happens when the person who’s always figured it out—suddenly doesn’t know what’s next? In Episode 2 of  Gen-X Crisis , Robert talks with his brother-in-law Gavin De West, a veteran of the film and TV industry whose 25-year career as an assistant property master was all about solving problems under pressure. Now in his 50s, Gavin finds himself in unfamiliar territory: between jobs, rethin...