Gen X Crisis with Robert Guess

Gen X Crisis with Robert Guess
Podcast Description
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.
Podcast Insights
Content Themes
The podcast delves into themes such as aging, reinvention, and the midlife experience, highlighting topics like the exhaustion of a lengthy career, the disorientation of societal changes, and redefining ambition. Episode examples include discussions on parenting teenagers, the shift in success metrics, and navigating personal challenges like dementia, all framed through relatable humor and honesty.

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.
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.

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