The Difficulty: Creativity, Meaning & the Hard Work of a Life

Dr. Chad Prevost
  • 5.0 (39)
  • Self-Improvement
  • Updated Weekly

The Difficulty is a podcast about creativity, meaning, and the hard choices that shape a life. Each week, writer and publisher Chad Prevost works through the questions underneath the creative process and the examined life—how we make work that matters, sit with life's difficulties instead of rushing past them, and keep going. Expect arguments, reflections, and the occasional witness to something worth seeing. Slower, more contemplative episodes land on Saturdays. It's also the voice of Crossroads Publishing Group, a press built on a single idea: books are occasions for community. If you're a creative, a thinker, a maker, or anyone navigating the difficulty of doing meaningful work—pull up a chair. chadprevost.substack.com

  1. Working Writer: The Money Moved

    3d ago

    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

    25 min
  2. Crossings: The 64-Page Book That Knows Where You Are

    6d ago

    Crossings: The 64-Page Book That Knows Where You Are

    How many books on your shelf were actually finished (if they were even began)? This episode is about a different kind of book: short on purpose, beautiful enough to keep, written from the far side of a hard turn for the person standing in it now. A case for concentration over padding, and the first look at Crossings, our new short-form line. Find 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

    20 min
  3. Weekend Reflection: Penelope at the Loom

    Jun 20

    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

    22 min
  4. Writing By Hand in the AI Era

    Jun 18

    Writing By Hand in the AI Era

    I did an episode a few weeks back on Jasmine Sun’s provocations about independent writing in the AI era. One of those provocations: the value of polish is going down, and the value of personal style, charisma, and weirdness is going up. AI is very good at polished prose. AI is bad at voice—the particular moves only this writer would make, the typos the writer would have caught but didn’t, the metaphor that shouldn’t work but does because it’s coming from this particular mind. Sun’s frame and the longhand frame meet exactly here. Voice is the comparative advantage. Voice is what AI cannot generate. And handwriting is one of the most reliable disciplines we have for preserving and developing voice. Here’s why. When you type, autocomplete and muscle memory and the smoothness of the keyboard tend to push you toward standard phrasings. The fastest sentence to type is usually the most expected sentence. AI tools accelerate this further by suggesting the most predictable next phrase. Even without AI, typing tends to homogenize prose toward the average. When you write by hand, none of that exists. There is no autocomplete. There is no suggestion engine. There is only the pen and the next word, and the speed limit is your thinking. The sentence you write is the sentence you composed in your head and chose to put down. The sentence is unmistakably yours because nothing intervened between your mind and the page. In the AI era, the handwritten draft is not nostalgic. It is maximally human. It is the most reliable way to produce prose that could not have been generated.Here’s something I’d like you to try. Write your next essay—or a chapter—by hand. Don’t do it for one session. Do it for a few weeks, long enough to get into a flow. See what emerges that doesn’t emerge at the keyboard. If you do it, write me back and tell me what you found. --- WHY THIS KEEPS COMING UP I’m writing this partly because the original Medium article keeps showing up in my analytics every month, even though I wrote it years ago. Writers are looking for ways to think about the question of HOW THEY WRITE in a moment when the answer is contested. The longhand discipline is one answer that hasn’t gone out of fashion in the lifetimes of the writers I just named, and I don’t think it’s going out of fashion now. If anything, the AI moment makes it more important. If you’re working on something and you want a publisher who’ll talk to you about voice and craft and the actual practice of writing—not just the production at the end—Crossroads is that press. Discovery call on the site. Twenty minutes, free. The difficulty in life is the choice. —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

    26 min
  5. Opening the Doors: The Crossroads Commons

    Jun 15

    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 → chad@crossroadspublishing.group Most 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 Commons The 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

    22 min
  6. Weekend Edition: What Have You Ever Gained from Witholding?

    Jun 13

    Weekend Edition: What Have You Ever Gained from Witholding?

    This is one of the slower Saturday episodes—no announcements, no news. Just a piece of the book I’m writing, read and thought through out loud. It starts on Circe’s island, where Odysseus’s men have already been turned into pigs. It passes through Dante’s hell, where the greedy push boulders forever, and through Midas’s palace, where a father reaches for his daughter and finds cold metal. And it ends somewhere closer to home: the quiet withdrawal, the measured non-engagement, the parts of ourselves we’ve decided are too valuable or too vulnerable to share. Because here’s the thing about Avarice: in its deepest expression, it was never about gold. It’s a misdirected search for transcendence. We’re not hoarding money, we’re hoarding self. Time, warmth, attention, the willingness to be known. And the endpoint of all that protecting isn’t wealth. It’s isolation. Two questions sit at the center of this one: What are you unwilling to give? And what is that withholding costing the people who need you? If the episode does something to you, here’s the assignment, which is also the argument: share it with one person you’ve been quietly withholding from. —Chad P.S. — Monday’s episode is different. I have an announcement about the press, about what we’re building, and about how you can be part of it. It’s the most excited I’ve been about anything in a while. Come back Monday. 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

    20 min
  7. The Questions a Serious Editor Asks of a Manuscript

    Jun 11

    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 remaining Each 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

    35 min
  8. The AI Conversation Just Shifted. Here's a Short Survey of Different Approaches.

    Jun 8

    The AI Conversation Just Shifted. Here's a Short Survey of Different Approaches.

    WHAT’S EMERGING AND WHAT IT MEANS The 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

    29 min
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The Difficulty is a podcast about creativity, meaning, and the hard choices that shape a life. Each week, writer and publisher Chad Prevost works through the questions underneath the creative process and the examined life—how we make work that matters, sit with life's difficulties instead of rushing past them, and keep going. Expect arguments, reflections, and the occasional witness to something worth seeing. Slower, more contemplative episodes land on Saturdays. It's also the voice of Crossroads Publishing Group, a press built on a single idea: books are occasions for community. If you're a creative, a thinker, a maker, or anyone navigating the difficulty of doing meaningful work—pull up a chair. chadprevost.substack.com

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