Gen X Crisis with Robert Guess

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 competiti...

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...

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 ab...

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 ...

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 tec...

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 e...

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 ...