Gen X Crisis with Robert Guess
Claim This Podcastby Robert Guess
Podcast Overview
<blockquote><strong>Gen X Crisis</strong> 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?</blockquote><p><br></p><p>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.</p><br><p>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.</p><br><p>New episodes every week. Learn more or sign up at <a href="https://www.genxcrisis.com/" rel="noopener noreferrer" target="_blank"><strong>www.genxcrisis.com</strong></a> to get updates via Substack.</p><hr><p style='color:grey; font-size:0.75em;'> Hosted on Acast. See <a style='color:grey;' target='_blank' rel='noopener noreferrer' href='https://acast.com/privacy'>acast.com/privacy</a> for more information.</p>
Language
🇺🇲
Publishing Since
6/3/2025
1 verified contact email on file for Gen X Crisis with Robert Guess
Pitch yourself as a guest, propose sponsorships, or reach out directly to the host.
Recent Episodes
November 25, 2025
Crisis Averted w/Robert Guess (Season 1 Finale)
<p>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.</p><br><p>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. </p><br><p>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.</p><br><p><strong>I reflect on the big themes that emerged across the season:</strong></p><br><p>• <strong>The psychedelic trip of being in your 50s</strong> in a world you barely recognize</p><p>• <strong>The trap of nostalgia</strong> and how quickly you can start feeling old</p><p>• <strong>The Gen X playbook we inherited</strong> - especially around not self-promoting, keeping your head down, and how that shapes our lives today</p><p>• <strong>The physical side of aging</strong>, and how much it impacts our mental state</p><p>• <strong>The power of staying connected</strong> when your instinct is to isolate</p><p>• <strong>Why reinvention is not optional</strong> - and might actually be the best part of midlife</p><br><p>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.</p><br><p>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.</p><br><p>Season 1 was about getting out of my crisis. Season 2 is about what comes next.</p><br><p>Thanks for being part of this.</p><p>See you in January.</p><br><p>Visit <a href="http://www.genxcrisis.com/" rel="noopener noreferrer" target="_blank"><strong>www.genxcrisis.com</strong></a> to subscribe and get updates on Season 2.</p><hr><p style='color:grey; font-size:0.75em;'> Hosted on Acast. See <a style='color:grey;' target='_blank' rel='noopener noreferrer' href='https://acast.com/privacy'>acast.com/privacy</a> for more information.</p>
November 18, 2025
Gen Maxxing w/Felix McCormick
<p>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.</p><br><p>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.</p><br><p>Robert and Felix talk about:</p><br><p>• What Gen Z really thinks Gen X got righ and wrong</p><p>• The collapse of the social contract how Gen Z is responsing</p><p>• Why extremism and polarity is rising among young people</p><p>• Meme culture, absurdity, and what’s actually funny now</p><p>• How social media shapes identity and politics</p><p>• Parenting (from both sides), agency, and the traps Gen X falls into</p><p>• What gives Gen Z hope in a chaotic, accelerating world</p><p>• The philosophy that guides him, and the life he’s building in Ireland</p><br><p>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.</p><br><p>Visit <a href="http://www.genxcrisis.com/" rel="noopener noreferrer" target="_blank">www.genxcrisis.com</a> to subscribe to Robert’s Substack and get exclusive updates.</p><hr><p style='color:grey; font-size:0.75em;'> Hosted on Acast. See <a style='color:grey;' target='_blank' rel='noopener noreferrer' href='https://acast.com/privacy'>acast.com/privacy</a> for more information.</p>
November 11, 2025
Embracing Uncertainty w/Jonathan Small
<p><strong>What if uncertainty isn’t something to escape but the space where reinvention begins?</strong></p><br><p>In this episode of Gen X Crisis, Robert talks with journalist, podcaster, and Substack writer <strong>Jonathan Small</strong>, 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.</p><br><p>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.</p><br><p>This one’s about letting go of control, trusting your instincts, and realizing that “not knowing” can be the start of something new.</p><br><p>Visit <a href="http://www.genxcrisis.com/" rel="noopener noreferrer" target="_blank">www.genxcrisis.com</a> to subscribe to Robert’s Substack and get exclusive updates.</p><br><p>And check out Jonathan Small’s Substack, <a href="https://jonsmalltalk.substack.com" rel="noopener noreferrer" target="_blank">Small Talk</a>, and his best selling book <a href="https://writeaboutnowmedia.com/book" rel="noopener noreferrer" target="_blank">Write About Now</a>, interviews with over 400 writers in journalism, fiction, non-fiction.</p><hr><p style='color:grey; font-size:0.75em;'> Hosted on Acast. See <a style='color:grey;' target='_blank' rel='noopener noreferrer' href='https://acast.com/privacy'>acast.com/privacy</a> for more information.</p>
26 total episodes available
Recent guests on Gen X Crisis with Robert Guess
Guests from recent episodes — sign up to see every guest that has ever appeared on this show.
Kristin Cifelli
Guest
Ed Greenberger
Guest
Robert Field
Guest
Dana DuBois
Guest
Gavin De West
Guest
Gary Rosenson
Guest
Deep-dive analytics for Gen X Crisis with Robert Guess
Frequently asked questions
Have a different question and can't find the answer you're looking for? Reach out to our support team by sending us an email and we'll get back to you as soon as we can.
- What is Gen X Crisis with Robert Guess?
<blockquote><strong>Gen X Crisis</strong> 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?</blockquote><p><br></p><p>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.</p><br><p>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.</p><br><p>New episodes every week. Learn more or sign up at <a href="https://www.genxcrisis.com/" rel="noopener noreferrer" target="_blank"><strong>www.genxcrisis.com</strong></a> to get updates via Substack.</p><hr><p style='color:grey; font-size:0.75em;'> Hosted on Acast. See <a style='color:grey;' target='_blank' rel='noopener noreferrer' href='https://acast.com/privacy'>acast.com/privacy</a> for more information.</p> - How often does this podcast release new episodes?
This podcast updates daily.
- Where can I listen to this podcast?
This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
- Does this podcast accept guests?
Yes, this podcast regularly features guests.
Legal Disclaimer
Pod Engine is not affiliated with, endorsed by, or officially connected with any of the podcasts displayed on this platform. We operate independently as a podcast discovery and analytics service.
All podcast artwork, thumbnails, and content displayed on this page are the property of their respective owners and are protected by applicable copyright laws. This includes, but is not limited to, podcast cover art, episode artwork, show descriptions, episode titles, transcripts, audio snippets, and any other content originating from the podcast creators or their licensors.
We display this content under fair use principles and/or implied license for the purpose of podcast discovery, information, and commentary. We make no claim of ownership over any podcast content, artwork, or related materials shown on this platform. All trademarks, service marks, and trade names are the property of their respective owners.
While we strive to ensure all content usage is properly authorized, if you are a rights holder and believe your content is being used inappropriately or without proper authorization, please contact us immediately at hey@podengine.ai for prompt review and appropriate action, which may include content removal or proper attribution.
By accessing and using this platform, you acknowledge and agree to respect all applicable copyright laws and intellectual property rights of content owners. Any unauthorized reproduction, distribution, or commercial use of the content displayed on this platform is strictly prohibited.