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 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.

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