Gen X Crisis with Robert Guess
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.
Episodes
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 i...
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 songwriting in Catholic school to co-w...
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 career, and why walking away can so...
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 17,000 Uber rides, and what stand-u...
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, the risks of sharing personal ...
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, rethinking his future, and asking bi...
What happens when you’ve climbed the ladder, raised your kids, and still can’t figure out how to slow down?
In this first episode of Gen-X Crisis, Robert sits down with longtime friend and TV executive Gary Rosenson for a raw, funny, and reflective conversation on what it actually feels like to hit your 50s and still be spinning your wheels.
Robert and Gary talk about the exhaustion that creeps in after decades of ...
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