PODCAST · education
Leading Human
by Chad Prevost
You've achieved the success. You've checked the boxes. But something still feels off.Welcome to Leading Human—a podcast for high-achieving leaders, founders, and mission-driven professionals who are questioning whether the life they built is actually the life they want. This isn't about productivity hacks or surface-level self-care. This is about the real work: reclaiming your authentic self beneath the conditioning, the burnout, and the unconscious patterns running your life.Hosted by Chad Prevost (and sometimes Shelley), co-founders of Big Self School, Leading Human explores conscious leadership through the lens of depth psychology, the Enneagram, and the emerging role of AI in human development. We believe burnout isn't something that happens *to* you—it's something that happens *for* you. It's a soul crisis revealing where you've been abandoning yourself.Each episode tackles the friction between who you are and who you've become. We explore how personality operates beneath the s
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258
Write the truest sentence you know
I had sixty-thousand words then I had twenty-thousand, and I still did not have a book. This Thursday’s episode is about how I finally learned the difference, and it’s the most useful thing I know about the work.The manuscript had frameworks. It had seven tidy maps. It had the warm, encouraging, here-are-your-steps voice I’d spent years building. And every time I read it start to finish, something was wrong and I couldn’t name it. That’s not writer’s block. It’s quieter and worse: the slow realization that a pile of genuinely good material is not a book. In Vivian Gornick’s terms, I had a situation. I didn’t have a story.The way out came from Hemingway, broke and young in a cold Paris garret, who when he couldn’t get started would tell himself, “Write the truest sentence that you know.” Just one. But here’s the part everyone skips: he also cut to it. Whenever he caught himself writing elaborately, presenting something, he’d throw that ornament away, what he called the scrollwork, and start from the first true simple sentence. The truest sentence isn’t something you add. It’s what’s left when you cut the performance off.So I went hunting through my thirty-seven thousand words for the one place I’d stopped performing and actually said the thing. Then I found the sentence. Everything that served it stayed. All seven maps, the whole coaching voice blog posts, went over the side as ballast, and the book finally floated—well, it’s floating.You’re allowed to not know your true sentence yet. You almost never do going in. You write the messy draft precisely to find the one true thing hiding in it. You’re allowed to have a pile that isn’t a book yet, that’s just the middle, everyone’s middle looks like a pile. And you’re allowed to cut what you love. In fact you have to.Listen above. Then, if you want, reply and tell me the one true sentence your project is really about, or the one you suspect you’ve been avoiding.“The truest sentence isn’t something you add to your draft. It’s what’s left when you cut the performance off.”The Difficulty lands Mondays, Thursdays (the working writer), and sometimes Fridays and sometimes Saturdays (from the workshop). If this named something you’ve been circling, subscribe, and forward it to someone with a pile that’s trying to become a book. More at chadprevost.com. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit chadprevost.substack.com
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257
Locate yourself
I went out to play disc golf yesterday, and I kept losing focus on the game. My mind wandered off down every side trail in the woods. This Monday’s episode follows a few of those trails.We start with the poem you think you know. “The Road Not Taken” gets read as an anthem for bold nonconformists, but read the middle again: the two roads “equally lay in leaves no step had trodden black.” There was no road less traveled, not really. Frost isn’t describing a choice. He’s describing the story he already knows he’ll tell about it, “with a sigh,” years from now. The difficulty is the choice. But underneath it is a harder thing: knowing where you’re actually standing when you make it.From there we get lost on purpose. The way some languages orient by north and south instead of left and right, and how our ancestors located their very identity in place. Satoshi Kon’s Perfect Blue and the terror of losing your self coordinates entirely. And the strange argument between Walt Whitman, who blessed the multitudes we contain, and Gurdjieff, who sat with a more accusatory tone toward those same sleepwalking multitudes.What I carried out of the woods were three questions: What are we actually, consciously choosing? Why do we spend so much energy distracting ourselves from ourselves? And why is it so hard to know who we are?And one small piece of permission, which is what we do here on Mondays. You don’t have to travel both roads, catch every fleeting thought, or unify the crowd inside you into one tidy self. You only have to remember yourself among them. Be the quiet one who watches the parade without climbing aboard every float. That’s the fixed point. That’s what it means to locate yourself.Listen above. Then, if you want, reply and tell me your one fixed point, the thing you orient by when everything else is just trees.The Difficulty lands Mondays (the long walk), Thursdays, and Saturdays. If this located something in you, subscribe and forward it to one person who’s feeling turned around. More at chadprevost.com. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit chadprevost.substack.com
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256
The Difficulty: live from The Home Bar with co-host Genesis the Greykid
The difficulty in life is the choice. And this week the choice came fast: an hour before we sat down, a tree took a lightning strike around the corner, dropped a branch on a woman’s car, smashed a transformer, took out the block. Genesis’s people — Josh, Kyle — ran toward it and pulled her out. Then they walked over and made a podcast about the creative life.That’s the register of this second episode, recorded at the corner of 4th and Market, the intersection of a city that is itself a crossroads. Genesis poured a Scotch bottled somewhere between 1929 and 1940 — a hundred years in someone’s collection, traded for one of his paintings — and we talked about permanence, and how the people from a hundred years ago are speaking more resonantly to us than ever. (No, that pour you hear is not AI. That’s the real thing.)Some of what we got into:* The Waffle House poet. Genesis met a woman writing “immaculate poetry” at 3 a.m. who’s been at it twenty years and is certain it’s not for her. The whole episode circles back to her: the gap between a real gift and the permission to claim it.* The compromises we make with ourselves. From a Seinfeld bit about the trashman to Chad’s first year of seminary mopping floors as “the minister to commodes” — the dignity of honest work, and the moment a gift asks to be shared anyway.* When to keep going, and when to stop. Bukowski’s twenty years at the post office. The friend who built a $50M company and blew it up because chaos was his home. The bandmate who wouldn’t sign the deal. If you love the work like you love ice cream, the sugar high fades. If you love it like you love your children, you keep going — even if it costs you.* What is good art? Bob Dylan’s voice. The mystery in Roethke’s line, “Light takes the tree; but who can tell us how?”* The invisible layer. John O’Donohue’s “invisible choreography” between the heart and what it beholds — and how the receiver often finds something in the art the maker never knew was there.Two poems. Chad read Theodore Roethke’s villanelle “The Waking” (“I wake to sleep, and take my waking slow. / I learn by going where I have to go.”) — and Genesis answered with Chase Twichell’s subway poem, the one that ends on “I don’t know who speaks / when the horse speaks.” Then Kyle Kasper, a poet who moved to Chattanooga last year and just published his first collection — and who’d run out to that wrecked car an hour before — read his own poem, “Kind to Me”: “We must be kind to ourselves… be good to your soul, like you would to a child.”We closed on the question we’re keeping: What are you alive to right now? And what are you closed to? Genesis is alive to the opinion that challenges his own — “if nobody likes you, I wonder why not; let’s hang.” And what he’s closed to turned out to be the most open thing he said all night: the God question, from an experience in a 2002 storm he can’t un-know. “I don’t have the answers, but I have the experience.”Listen above. New conversations from The Home Bar, and Mondays and Thursdays wherever you get your podcasts.From Chattanooga, a crossroads city, at a bar on an intersection — this is The Difficulty. Brought to you in part by Crossroads Publishing Group. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit chadprevost.substack.com
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Working Writer: The Money Moved
Five things that actually moved in publishing this month, and what to do about each. The Authors Guild puts hard numbers on why author income keeps slipping, Audible forces a year-end decision on audiobook royalties, FSG opens a no-fee $15,000 fellowship (deadline July 6), book discovery starts shifting from search to AI, and the indie bookstore "death" turns out to be growth. The channels you don't control are getting harder, so put your weight on the ones you do.Join us at crossroadspublishing.group. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit chadprevost.substack.com
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254
Weekend Reflection: Penelope at the Loom
Homer gives us a woman who weaves a shroud by day and unravels it by night, holding off a house full of suitors. We call it stalling. Homer calls it devotion. This one is for anyone whose truest work looks, from the outside, like waiting: the patient no, the thing left undone on purpose, the refusal to finish on someone else's terms.Find us at https//:www.crossroadspublishing.group. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit chadprevost.substack.com
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Opening the Doors: The Crossroads Commons
TL;DRToday we open the doors. Crossroads Publishing Group—a hybrid publisher of serious nonfiction in Chattanooga—announces the Crossroads Commons, our founding membership. Three tiers; fifty lifetime Founder spots, ever.• Join the Commons → crossroadspublishing.group/commons• Publish with us → crossroadspublishing.group/engagements• The catalog → crossroadspublishing.group/catalog• Questions → [email protected] small presses spend their first year trying to look like a big press. We’re not doing that. A hybrid publisher of serious nonfiction, based in Chattanooga, founded this year, built around the idea that books are occasions for community—and that the press’s job is to take that seriously.The Long StoryA few weeks ago I made a decision about how Crossroads Publishing Group would set itself apart: a real commitment to relationship. Then, on a mountain bike trail a few days ago, the bigger version of the idea arrived. It’s not just relationship—one-on-one, editor and author. It’s community. And once you see it, you can’t unsee it: leadership books end at community. Recovery books end at community. Theology, parenting, loneliness, climate—trace the actual argument and the topic turns out to be the doorway in. Community is the thing itself.So I’m building the press to take that seriously, not as a marketing line, but as operating structure. Today’s episode lays out the whole thing.Five structural commitments:* Every Crossroads author gets a direct-purchase URL for their community—their people buy from the press, their royalty is higher, and the relationship stays out of the algorithm.* Every book launches with an event in the author’s community, wherever they live.* Every Crossroads author appears on The Difficulty.* Authors meet each other—the catalog becomes a community of minds, not a list of titles.* Readers get a structured way to belong to the press: the Crossroads Commons, open today.The Commons, three tiers:* Reader — $200/year. Every new title shipped to your door on publication day. A quarterly Circle Letter. 20% off direct orders. Your name in the colophon of every title shipped during your membership year.* Patron — $500/year. Everything above, plus a signed limited-edition hardcover each year (printed exclusively for Patrons), an invitation to the annual Crossroads gathering, private author Q&As at every launch, and 30% off.* Founder — $1,000, one time, lifetime. Limited to the first 50, ever. All Patron benefits in perpetuity, your name permanently in the colophon of every title we publish during your lifetime, and one annual meal or coffee with me. When the 50 are filled, that door closes forever.The Commons isn’t a subscription to this podcast, The Difficulty stays free, always. It’s membership in the press itself. And you shouldn’t join from obligation or scarcity pressure. Join because the editorial direction and the community we’re forming matter to you, and you want to be part of the early conversation.→ Join the Crossroads CommonsThe four doors, if you’re wondering which is yours:* Authors — from a $750 Legacy Audit to the full Compile to Publish engagement (print + ebook + audiobook, six to eight months): crossroadspublishing.group/engagements* Readers — the Circle: crossroadspublishing.group/circle* Writers developing a manuscript in community — the First Draft Cohort, applications open July 13, inaugural class begins September 14.* Just want a book? — crossroadspublishing.group/catalog — William James’s The Varieties of Religious Experience is in print now; Virginia Woolf’s A Room of One’s Own is next (and I’m narrating the audiobook myself)This is your moment to step in.—Chad This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit chadprevost.substack.com
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The Questions a Serious Editor Asks of a Manuscript
Monday’s episode last week was about green-lighting yourself, refusing to wait for institutions to validate your work. Today we go one layer deeper. Green-lighting yourself does not mean publishing whatever you’ve got. It means doing the editorial work seriously, on your own behalf, so what you publish is actually ready.Editorial direction is more specific than most writers think. Here are six questions a serious editor asks of a manuscript before saying yes to it. You can start asking these of your own work today.* What is this book actually about* Who is the reader* What shelf does this book sit on* What is the reader’s journey* Where is the prose working and where is it slipping* What is the work remainingEach question comes with an exercise you can do on your own manuscript right now.This episode also covers when outside editorial direction is most useful (later than most writers think) and what Crossroads’s Editorial Framing Brief actually provides for writers who have done their own work and still can’t see what they’re missing.If you’re working on a manuscript and want a publisher who thinks this way about the editorial standard—voice, testimony, weight per paragraph—Crossroads is that press.We’re in our founding season through summer 2026 with founding-rate engagements.Discovery call → 20 min, free, let’s chat.Author Engagement and First Draft Cohort here!—Chad This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit chadprevost.substack.com
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The AI Conversation Just Shifted. Here's a Short Survey of Different Approaches.
WHAT’S EMERGING AND WHAT IT MEANSThe question is shifting from “should writers use AI” to “what kind of writing is worth doing.” Tim Moon argues the shame regime around AI use is making honest conversation harder. The Atlantic piece shows the detection question is real but temporary — and the deeper question is what’s lost when the thinking that produces writing goes away. Ramachandran shows the Commonwealth Prize fiasco was really a story about what we’d been rewarding. Sun and Morine both argue the writer’s comparative advantage is not the absence of AI but the presence of voice and testimony and the kind of writing only this writer would do.For the writers I’m trying to publish at Crossroads—for the writers in the cohort, for the writers I’m talking to in discovery calls—this is the frame I want to model. We are not the press that takes a position on AI. We are the press that asks whether every paragraph is bearing weight, whether the voice on the page is the writer’s voice, whether the manuscript contains things the writer brought back from somewhere only they have been.Those questions can be asked of a manuscript written entirely by hand or one written with AI assistance or anything in between. The questions are the editorial standard. The tools the writer used to get there are the writer’s business.What’s freeing about this conversation is that it lets serious writers be honest about their actual practice without performing a position. That’s what Sun and Ramachandran and Moon and Morine are doing. That’s the tone I want for Crossroads, for the show, and for the writers we’re working with.THE READING LIST- Sanjana Ramachandran, The Print — Should we leave writing to AI?- The Atlantic — How to Tell AI Writing (May 2026)- Tim Moon, Substack — AI: The Scarlet Letters- Jasmine Sun, jasmi.news — Comparative Advantage of Independent Writers- Nicholas Morine on LinkedIn — Mile Wide, Inch Deep---If you’re working on a manuscript and want a publisher who thinks this way about the editorial standard—voice, testimony, weight per paragraph—Crossroads is that press.We’re in our founding season through summer 2026 with founding-rate engagements.Discovery call → 20 min, free, let’s chat.Author Engagement and First Draft Cohort here!—Chad This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit chadprevost.substack.com
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ABOUT THIS SHOW
You've achieved the success. You've checked the boxes. But something still feels off.Welcome to Leading Human—a podcast for high-achieving leaders, founders, and mission-driven professionals who are questioning whether the life they built is actually the life they want. This isn't about productivity hacks or surface-level self-care. This is about the real work: reclaiming your authentic self beneath the conditioning, the burnout, and the unconscious patterns running your life.Hosted by Chad Prevost (and sometimes Shelley), co-founders of Big Self School, Leading Human explores conscious leadership through the lens of depth psychology, the Enneagram, and the emerging role of AI in human development. We believe burnout isn't something that happens *to* you—it's something that happens *for* you. It's a soul crisis revealing where you've been abandoning yourself.Each episode tackles the friction between who you are and who you've become. We explore how personality operates beneath the s
HOSTED BY
Chad Prevost
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