Infinite Loops Podcast
Episode 289: Michael Perry — Improbable Mentors and the Art of Midwestern Storytelling
Host: Jim O'Shaughnessy
Guest: Michael Perry
Date: November 6, 2025
Episode Overview
In this lively and deeply authentic conversation, Jim O’Shaughnessy hosts Michael Perry—humorist, author, volunteer firefighter, songwriter, and quintessential Midwesterner—for an exploration of “improbable mentors” and the rich tradition of Midwestern storytelling. The episode covers Perry’s circuitous path through writing, why practical wisdom and humility remain foundational virtues, navigating the publishing industry, finding mentors in unexpected places, and the enduring lessons of service and kindness. Woven throughout are candid memories, gentle self-deprecation, and a seamless blending of humor and earnest insight—a celebration of ordinary wisdom and the people who carry it.
Key Themes & Discussion Points
The Accidental Author & Permissionless Action
- Michael Perry’s Origin Story: Perry shares he never set out to be a writer, highlighting a career built on serendipity, hard work, and persistence rather than life-long ambition.
"I've never set a goal. I never dreamed of being a writer. I just wandered into it and discovered the thing I love."
(02:33) - Luck + Grit: Perry stresses the interplay of luck and hard work in creative careers. He links his modest financial security to both fortune and small acts, like investing the first real writing check.
- On Taking Initiative: He’s inspired by the idea of “permissionless action”—doing, rather than waiting for outside validation.
"I look back and I go, yeah, that's pretty much what I was doing... I was writing letters to people I had no business writing letters to."
(03:19)
Midwestern Roots, Blue-Collar Identity, and Storytelling
- The Weight (and Value) of Blue-Collar Upbringing: Perry talks candidly about the tension between his writing career and his family’s tradition of hard, tangible labor, emphasizing humility and keeping oneself “small w” in a “capital A” Arts world.
“Where I come from, if you can't stack it or stack with it, it don't count. And that includes a stack of books.”
(10:22) - On Never Quite Belonging: There’s an ever-present feeling of being an outsider in literary circles, mitigated by the validation of success and publisher names.
- Midwestern Humor & Practical Wisdom: Both host and guest extol the understated, “do the work” Midwestern ethos—shaped by family, context, and the expectation you shouldn’t get too big for your boots.
"If, when you're done with your task, you find the person in charge of you and say, what can I do next? You're gonna be fine."
(34:05)
Mentorship in the Unlikeliest Places
- Improbable Mentors: Perry’s new book collects the unexpected wisdom picked up along the way—from grandfathers, blue-collar coworkers, firehouse peers, and even cantankerous neighbors.
- On Regrets & Asking Questions: Sometimes mentors teach by omission, leaving lessons in the gaps.
“You can't necessarily seek wisdom. You can't seek a mentor. It’s like pushing a rope. It’s just going to knot up and trip you. You just got to put yourself in their presence.”
(91:16) - Practical Integrity: Perry recalls his grandfather saying you can be honest and still succeed—“Now, telling the truth creatively...” (19:36).
Publishing: The Traditional, the Hybrid, and Self-Invention
- Gratitude—and Frustration—with Big Publishing: Both men credit major publishers for their careers, yet detail how old models fail to truly support contemporary authors, especially regarding publicity and royalties.
“At some point it becomes clear it’s not going to change and it’s not personal and it’s not animus, it’s just the machine.”
(44:13) - DIY & Iteration: Perry shares stories of directly selling hundreds of books at volunteer firefighter conventions, having learned publishers would not understand “those people just aren’t readers”—a stereotype handily disproven at every event.
“If you give me 45 minutes to tell the story in their vernacular... they see it coming through someone who’s actually served beside them.”
(46:53) - Why the Writing Life Is Iteration, Not Blueprint: On “happy tangents” and Ken Stanley’s “Greatness Can’t Be Planned,” both agree life is far richer if you let curiosity and circumstance drive your path.
Everyday Heroism and Authenticity
- Turning Down Oprah: In a story highlighting both humility and ethical clarity, Perry explains why he declined a spot on Oprah—he wouldn’t go on as the “hero” the show wanted, preferring honesty about the realities of being a first responder and of HIV in rural areas.
"If you want me to come on and talk about HIV and AIDS and trying to educate ourselves out here in the hinterlands, I'll do that... I just said no."
(71:00) - The Reality of Emergency Work: First responder work grounds Perry in practical humility, reminding him daily of mortality, the limits of toughness, and the fleeting nature of accomplishments.
“I have watched the toughest, baddest dude in town weep in pain... I never forget that that could be me at any minute. I don’t care how tough you are.”
(82:01)
Navigating Change: From MFA Paths to Artificial Intelligence
- On the Realities of the Writing Industry: Many aspiring writers operate as if the old publishing world still exists. Perry gently advises understanding the real landscape: writing is a hustle, practical as much as poetic.
- Technology, Adaptation, and the Impossible Dream:
“Don’t be bitter and don’t be brittle... You can be disappointed for 20 minutes, but then you just get back to it and find the new path.”
(101:32) - AI and Literary Theft: They recall Voltaire’s work being bootlegged in his time, noting that today’s technological threats are perennial—and that navigation is essential.
Notable Quotes & Memorable Moments
“Kindness is not weakness... empathy. Just wish there was more.”
— Michael Perry, (109:35)
“Never stand behind a sneezing cow.”
— Michael Perry, practical Midwestern wisdom (109:55)
“You just have to ask when’s the last time they pooped.”
— Michael Perry, on transferable skills from nursing to interviewing (94:19)
“Being too dumb to know when to quit.”
— Michael Perry, embracing persistence and the “reverse imposter syndrome” (61:56)
“If you can't stack it or stack with it, it don't count. And that includes a stack of books.”
— Michael Perry, on humble origins and validation (10:22)
“Listen, best practices from 1925 are... maybe you might want to update those a little bit.”
— Jim O’Shaughnessy, on the publishing industry (56:19)
“I’m a depressive optimist. Things really just keep going.”
— Michael Perry, on Scandinavian Midwestern temperament (79:47)
Timestamps for Major Segments
- [02:25] Jim introduces Michael Perry; discussion of Mark Twain, biography, and accidental paths
- [10:18] The struggle of blue-collar roots and finding value as a writer
- [13:57] On family storytelling, philosophy, and humility in the Midwest
- [14:17] American practical wisdom and “can-do” spirit—history, family, and hustle
- [27:02] The elements and ethos of Midwestern humor, humility, and storytelling
- [40:42] The “happy tangents” in life—nonlinear paths and the failures of mapped-out blueprints
- [46:29] Navigating publishing realities, self-publishing, and connecting with authentic audiences
- [62:11] On failing forward, autodidact approaches, and persistence
- [67:38] Turning down Oprah: when principles trump opportunity
- [78:58] Wisdom from first responders; reality vs. literary “rarefied air”
- [89:37] Improbable mentors: lessons from unexpected places
- [94:36] Getting to better interviews: asking the questions nobody else asks
- [99:43] The business of art—taking care of business to buy time to create
- [103:06] Bending, not breaking: adaptability as the artist’s survival
- [104:55] Voltaire, history, and the unchanging challenge of piracy and change
- [109:18] Emperor for a day: Michael’s two global messages—kindness isn’t weakness, and never stand behind a sneezing cow
Episode Tone & Style
The conversation is rich with gentle humor, confessional sincerity, and the unpretentious wisdom of people who have worked for, and often outside, the system. Both men strike a balance between nostalgia for old ways and a pragmatic embrace of whatever tools, challenges, or mishaps the present offers. Their exchange is equal parts a celebration of small-town wisdom, the power of story, and a clear-eyed reckoning with the realities (and absurdities) of adult life and creativity.
Takeaways
- Mentors don’t always arrive with titles. Everyday people—the neighbor, the grandparent, the colleague—often hold the greatest wisdom.
- Be pragmatic and adaptable. Whether in life or publishing, “brittle breaks”—the willingness to improvise, iterate, and do what isn’t done is key.
- Practical humility and kindness endure. In writing, business, and daily life, authenticity, empathy, and generosity are strengths, not weaknesses.
- Tell your own story, in your own way. Whether pitching books to the “wrong” crowd or asking country stars about their bus drivers, trust that specificity and honesty reach people.
- Success comes from showing up. Especially in a world of “happy tangents,” the best path isn’t always visible until after you walk it.
Closing (111:28)
Perry and O’Shaughnessy part with gratitude, sharing mutual respect for the practical wisdom gained through unlikely mentors, and promising a future continuation of their joyful, meandering conversation.
For more on Michael Perry’s writing, “Improbable Mentors and Happy Tangents,” and the tradition of Midwestern storytelling, visit newsletter.osv.llc for full transcripts, highlights, and more.