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 (https://www.genxcrisis.com/) to get updates via Substack.
Hosted on Acast. See acast.com/privacy (https://acast.com/privacy) for more information.
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 disorientation and loneliness, became the very thing that pulled me out of it.
I talk about reconnecting with old friends I hadn’t spoken to in decades, the surprising emotional depth of those conversations, and the recurring reminder (mostly from the women!) that maybe this isn’t a crisis at all… maybe it’s a reinvention.
I reflect on the big themes that emerged across the season:
• The psychedelic trip of being in your 50s in a world you barely recognize
• The trap of nostalgia and how quickly you can start feeling old
• The Gen X playbook we inherited - especially around not self-promoting, keeping your head down, and how that shapes our lives today
• The physical side of aging, and how much it impacts our mental state
• The power of staying connected when your instinct is to isolate
• Why reinvention is not optional - and might actually be the best part of midlife
I also share what I learned from hosting my first Gen Z guest, my stepson Felix, and why Season 2 will expand beyond Gen X, bringing in Gen Z, Millennials, and Boomers to round out the conversation.
This finale is a thank you, a reset, and a look forward. I talk about the guests who changed me, the friendships I wish I’d kept up, the community I want to build (especially for Gen X men who struggle to talk about this stuff), and why I’m more hopeful now than I’ve been in years.
Season 1 was about getting out of my crisis. Season 2 is about what comes next.
Thanks for being part of this.
See you in January.
Visit www.genxcrisis.com (http://www.genxcrisis.com/) to subscribe and get updates on Season 2.
Hosted on Acast. See acast.com/privacy (https://acast.com/privacy) for more information.
18 Nov 2025
Gen Maxxing w/Felix McCormick
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 part conversation, part reckoning, and part window into how Gen Z sees the future and Gen X.
Robert and Felix talk about:
• What Gen Z really thinks Gen X got righ and wrong
• The collapse of the social contract how Gen Z is responsing
• Why extremism and polarity is rising among young people
• Meme culture, absurdity, and what’s actually funny now
• How social media shapes identity and politics
• Parenting (from both sides), agency, and the traps Gen X falls into
• What gives Gen Z hope in a chaotic, accelerating world
• The philosophy that guides him, and the life he’s building in Ireland
It’s raw, honest, funny, and at times uncomfortable, in the best possible way. If the podcast has been about Gen X looking inward, this episode is about seeing ourselves through another generation's eyes.
Visit www.genxcrisis.com (http://www.genxcrisis.com/) to subscribe to Robert’s Substack and get exclusive updates.
Hosted on Acast. See acast.com/privacy (https://acast.com/privacy) for more information.
11 Nov 2025
Embracing Uncertainty w/Jonathan Small
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 about learning to adapt, create, and stay curious when the ground keeps shifting.
Rob and Jon explore the emotional terrain of midlife, the unease of not knowing what’s next, the quiet ache of fading relevance, and the paradox of finding freedom when the plan falls apart. They dig into how work, identity, and creativity evolve with age, and why embracing uncertainty may be the most honest way to live right now.
This one’s about letting go of control, trusting your instincts, and realizing that “not knowing” can be the start of something new.
Visit www.genxcrisis.com (http://www.genxcrisis.com/) to subscribe to Robert’s Substack and get exclusive updates.
And check out Jonathan Small’s Substack, Small Talk (https://jonsmalltalk.substack.com), and his best selling book Write About Now (https://writeaboutnowmedia.com/book), interviews with over 400 writers in journalism, fiction, non-fiction.
Hosted on Acast. See acast.com/privacy (https://acast.com/privacy) for more information.
Who has been a guest on Gen X Crisis with Robert Guess
Names identified in recent episode analyses. Showing up to five guests.
Kristin Cifelli
Ed Greenberger
Robert Field
Dana DuBois
Gavin De West
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
Apple Podcasts (US)
3.9 / 5
7 ratings
Contact Gen X Crisis with Robert Guess
Guest appearances
Books guests
Based on episode analysis; this does not confirm that the show is currently accepting guests.
Questions about Gen X Crisis with Robert Guess
Who hosts Gen X Crisis with Robert Guess?
Robert Guess host the show. Published by Robert Guess.
How often do new episodes come out?
The show publishes weekly, based on its RSS feed.
Does Gen X Crisis with Robert Guess take guests?
Yes. Guests have been identified in episode analyses.
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