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

Dr. Chad Prevost
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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

  1. 1d ago

    Why You Need to Hear from More Than Those Who Made It

    Almost every piece of writing advice you have ever received came from a survivor. In 1943 a statistician looked at where returning bombers had been shot and realized the military was about to armor exactly the wrong parts of the plane. This episode is about what his correction has to do with every craft book, agent story, and five-a.m. routine you've ever read, and why the most important information is the part that never made it back. Crossroads Publishing Group is my press. If you're sitting on a manuscript, a proposal, or an idea you can't shake loose, take a look at crossroadspublishing.group. And if you decide it isn't for you, that's a real answer and a good one. The difficulty in life is the choice. 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

    Why You Need to Hear from More Than Those Who Made It

  2. 2d ago

    The Detours Are Sacred: Chris Heuertz on Grief, Love, and the Myth of Arrival

    If you’ve spent any real time with the Enneagram, you’ve probably felt Chris Heuertz’s influence whether you knew his name or not. Chris is the author of seven books, including The Sacred Enneagram (foreword by Richard Rohr) and The Enneagram of Belonging, with an eighth on pilgrimage coming from Simon & Schuster. But the books came out of a life: nearly three decades of humanitarian work across 70 countries, years in the anti-trafficking movement, time serving alongside Mother Teresa in Calcutta. We recorded this a couple of weeks before his wedding, and I wanted it out in the world before he walks into that new life. We talk about learning to tell stories on a word processor in India, burying 700 of the women and children he served and what that does to a person, the end of a twenty-year marriage and the strange welcome into the human family on the other side of it, rewriting sloth for the Nines, what Eights actually feel under the armor, and why the detours are sacred and the arrival is a myth. The difficulty in life is the choice. Show-note links: * Chris’s site: chrisheuertz.com * The Sacred Enneagram and The Enneagram of Belonging (Bookshop.org) * Chris’s Substack: Sacred Detours * Instagram: @chrisheuertz * Subscribe to The Difficulty: chadprevost.substack.com * Listen on Apple Podcasts or Spotify. * The press where it all makes sense: crossroadspublishing.group * Chad’s site: 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

    The Detours Are Sacred: Chris Heuertz on Grief, Love, and the Myth of Arrival

  3. Aug 14

    Why Everyone Else's Book Is Doing Better

    You open the app and it seems like every writer you know is having a better year than you are. There’s a name for what’s happening in your head and it isn’t envy. Two psychologists went and read what NFL fans posted when the season schedule came out, and found that every single fanbase was certain their team had drawn the hardest one. Same thing is happening to you on a Tuesday night, and once you see the shape of it, it loses most of its power. Crossroads Publishing Group is my press. If you're sitting on a manuscript, a proposal, or an idea you can't shake loose, take a look at crossroadspublishing.group. And if you decide it isn't for you, that's a real answer and a good one. The difficulty in life is the choice. 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

    Why Everyone Else's Book Is Doing Better

  4. Aug 13

    Learn by Going

    Everyone has a GO button. Mine was a drawer holding seven unpublished choose-your-path books I finally published under my own name. What happened after? On what courage actually is (a heart energy, not a head energy), what it isn’t (recklessness refuses feedback; courage subscribes to it), and why the unlived life is the one certain loss.In this episode: * The confession: a decade in the drawer, three books shipped, and what the children’s book market taught me the hard way * David Whyte’s Consolations on courage as “heartfelt participation” * David Hawkins on courage at level 200 — the threshold where a life stops draining energy and starts giving it back * Dr. Spalding’s cliff: courage without readiness is just another form of impulse * Roethke’s permission: “I learn by going where I have to go” * Readings from my forthcoming nonfiction book, arriving January Bring us your book. Crossroads publishes serious nonfiction of the inner life—memoir, essay, contemplative work. Six openings remain for fall authors, and founding-author rates hold through September 30: $5,000 for a short book we call a Crossing, up to $7,000 for a full-length book, with the audio edition included in every tier. → Book the free 20-minute discovery call · See the engagement ladder · Tell us about your book in writing The pricing on the site is the pricing. On the horizon: our reissue of Virginia Woolf’s A Room of One’s Own (September 8) · Mirage and Tar, a numbered first edition of 100 copies, this fall · the book read from in today’s episode, January. 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

    Learn by Going

  5. Aug 7

    We Should Have Quit That Day

    Last week I told you to stick with things. This week I want to tell you about the afternoon Daniel Kahneman sat in a room, was handed the exact information that should have made him quit, and carried on as if nothing had happened. It cost him eight years, and the thing they were building was never used. I try to work out honestly which one of us is right. Crossroads Publishing Group is my press. If you're sitting on a manuscript, a proposal, or an idea you can't shake loose, take a look at crossroadspublishing.group. And if you decide it isn't for you, that's a real answer and a good one. The difficulty in life is the choice. 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

    We Should Have Quit That Day

  6. Jul 31

    Why We're Not Rational (And Never Were)

    A bat and a ball cost $1.10. The bat costs a dollar more than the ball. How much is the ball? If you said ten cents, you're in good company, because more than half the students at Harvard, MIT, and Princeton said the same thing. It's wrong. This episode is about why the wrong answer arrives so fast and feels so finished, and it starts with a seven-year-old boy in occupied Paris who turned his sweater inside out to hide the yellow star, and the SS officer who stopped him on the street. Crossroads Publishing Group is my press. If you’re sitting on a manuscript, a proposal, or an idea you can’t shake loose, take a look at crossroadspublishing.group. And if you decide it isn’t for you, that’s a real answer and a good one. The difficulty in life is the choice. 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

    Why We're Not Rational (And Never Were)

  7. Jul 30

    What Your Book Is Worth

    The Anthropic settlement got final approval, Amazon raised its royalty ceiling for the first time since 2007, and the first half sales numbers say something uncomfortable about nonfiction. Three answers to one question, and none of them came from a reader. The difficulty in life is the choice. If you’re sitting on a manuscript, a proposal, or an idea you can’t shake loose, Crossroads Publishing Group is my press. Editorial, design, print, ebook, audio, distribution. Take a look at crossroadspublishing.group and see what you think. If you decide it isn’t for you, that’s a real answer and a fine one. I also coach writers toward the harder part, which is hearing yourself into committing to the thing you actually want to do. That’s a conversation, not a purchase. And I’m taking on a handful of new projects this fall. If you know someone with a book they keep almost writing, or a story you know is worth telling, send them my way or just send me their name. 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

    What Your Book Is Worth

  8. Jul 28

    Speaking into the Wilderness

    I spent last week in a cabin outside Ellijay, Georgia, a couple of hours north of here. I’d thought about doing something more epic with my one week away, driving out to Chaco Canyon or somewhere like it, and then realized I’d spend most of the week driving and arrive exhausted. So, a cabin. I went to work on the nonfiction book I’ve been close to finishing and then taking apart again more times than I care to admit. I brought a lot of music gear with me too, just in case the writing didn’t go. Turns out that having only so much time is its own kind of help. I didn’t play much. This week’s episode came out of that. I want to talk to two people. The first has never written a book and can’t get past the question of who am I to do this. No platform. A few hundred people on Facebook, half of them from high school. Write the thing and you’re speaking into the wilderness. The second already wrote the book. It came out, it did fine or it didn’t, and now they’re quietly wondering whether it was worth what they gave it. Here’s the honest part, and I think the honest version is more useful than the pitch. Books don’t make people famous anymore. Even really good ones. That’s most of the reason the Big Five look for authors who already have an audience, because they aren’t in the platform-building business so much as the fire-to-it business. But a book is still a different form of distribution, and it reaches people who will never find you in a feed. Somebody they trust hands them a copy and says you should read this. That’s a door your other work doesn’t open. So the question I’ve landed on isn’t whether you should write a book. It’s whether you want to inhabit the identity of someone who writes. If you want somebody to read your one book, shouldn’t they be able to see that you’re a person who writes? I also get into why three-year and five-year plans have never worked for me, what David Perell’s 250,000 subscribers actually took in years, why a book that doesn’t sell in its first year is the moment most people quit and the wrong moment to do it, and my own fairly fragmented record of sticking with anything. The difficulty in life is the choice. If you’re sitting on a manuscript, a proposal, or an idea you can’t shake loose, Crossroads Publishing Group is my press. Editorial, design, print, ebook, audio, distribution. Take a look at crossroadspublishing.group and see what you think. If you decide it isn’t for you, that’s a real answer and a fine one. I also coach writers toward the harder part, which is hearing yourself into committing to the thing you actually want to do. That’s a conversation, not a purchase. And I’m taking on a handful of new projects this fall. If you know someone with a book they keep almost writing, or a story you know is worth telling, send them my way or just send me their name. 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

    Speaking into the Wilderness
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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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