The Difficulty

Dr. Chad Prevost
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The Difficulty is a show about the choices that shape a creative life, and the courage it takes to make them. Hosted by Dr. Chad Prevost, writer, publisher, and ICF-certified coach. Each episode explores a real decision point: craft, courage, failure, reinvention, and the stubborn belief that the work is worth doing. New episodes weekly. Subscribe for full episodes, transcripts, and Notes from the recording cutting-room floor. chadprevost.substack.com

  1. Waking in the Dark Wood: Midlife, Ego, and the Descent

    4D AGO

    Waking in the Dark Wood: Midlife, Ego, and the Descent

    Using Dante’s opening in the “dark wood,” host Chad Prevost frames midlife as waking up to being lost after sleepwalking through socially prescribed success, and reframes “abandon hope” as an instruction to stop relying on the old self and tools that created the crisis. He describes needing guidance beyond oneself, like Virgil leading Dante downward into the inferno to see the patterns that trap people, which he links to coaching clients’ pervasive belief “I am not enough,” shaped by culture or family systems. Drawing on Epictetus, Adler, Auden, and the Greek concept hamartia, he argues the ego’s protective adaptations become traps, and Dante’s hell illustrates suffering rooted in lies, from unconscious “errors” to willful avoidance; the series explores this descent as a path to a freer, fuller creative life.00:00 Saturday Series Intro00:58 Waking in the Dark Wood03:10 Midlife Lostness04:08 Abandon Hope as Instruction06:02 Virgil and the Descent07:45 The Not Enough Story10:43 Separating Self from History11:49 Hamartia and Ego Armor13:40 Truth Lies and the Circles15:35 Series Purpose and Farewell FREE — THE DIFFICULTY FIELD GUIDE Eight difficulties every working writer faces, and what to ask when each one shows up. → crossroadspublishing.group/assets/pdfs/The_Difficulty_Field_Guide.pdf — WHERE TO FIND ME Substack — new essays Wednesdays, the Working Publisher news digest Fridays → chadprevost.substack.com The Difficulty — Monday (the why), Thursday (the how), Saturday (essay readings) — wherever you listen to podcasts → chadprevost.com/the-difficulty Crossroads Publishing Group — publishing services, IF/THEN Books, the Iris Blackwood mystery series → crossroadspublishing.group — “The difficulty in life is the choice.” Get full access to The Descent at chadprevost.substack.com/subscribe

    17 min
  2. The Free Lunch Is Ending: Three Publishing Stories Worth Your Attention

    6D AGO

    The Free Lunch Is Ending: Three Publishing Stories Worth Your Attention

    If you're an indie writer paying attention to what's happening in publishing right now — this week was a tell. Three stories landed inside seven days. Each one pointed at the same answer.Episode 5 of The Difficulty — the first publishing-news episode in the new "How" lane. This week:— Audible's ACX royalty model is being discontinued. Authors must enroll in the new pooled, consumption-based model by year-end. Brandon Sanderson called this out back in 2024; Dave Chesson at Kindlepreneur is openly skeptical. Same playbook Spotify ran for music and KU ran for ebooks. Now it's audiobooks.— Publishing.com hit with a $1.5M FTC settlement — alleged misleading income claims and undisclosed incentivized testimonials. The publishing industry is being told publicly that some of the loudest "publish-your-book-and-get-rich" programs were misleading. Personal aside: I came close to laying out $6K to one of these a few years back. I'm glad I didn't.— Inkers Con runs May 30 – June 12 ($250, fully online). Working authors learning from each other in real time. Worth knowing about even if you don't go.The throughline: in a week where platforms got less predictable AND shady programs got FTC'd, the answer was the same answer indie writers have been circling for a decade. Direct audience. Real community. Owned email list. Less platform dependency.I share what I'm doing about it in real time — including how the Goodreads giveaway for Iris Blackwood pulled nearly 3,000 entrants, and the moment I almost didn't release Iris #1 as an ebook (and what changed my mind).—GO DEEPERFriday's Working Publisher Substack post extends this episode with sources and analysis:→ chadprevost.substack.com — search "The Free Lunch Is Ending"—CHAPTERSThree stories, same answerAudible's royalty pivotPublishing.com's FTC settlementThe $6K I almost spentInkers Con (May 30 – June 12)The throughline — direct audienceIris Blackwood anecdote — the ebook decisionClosing—FREE — THE DIFFICULTY FIELD GUIDEEight difficulties every working writer faces, and what to ask when each one shows up.→ crossroadspublishing.group/assets/pdfs/The_Difficulty_Field_Guide.pdf—WHERE TO FIND MESubstack — The Working Publisher (Fridays) + new essays Wednesdays + weekend essay readings Saturdays→ chadprevost.substack.comThe Difficulty — Monday (the why), Thursday (the how), Saturday (essay readings) — wherever you listen to podcasts→ chadprevost.com/the-difficultyCrossroads Publishing Group — publishing services, IF/THEN Books, Iris Blackwood mystery series→ crossroadspublishing.groupInkers Con:→ inkerscon.com/2026-digital-conference—The difficulty in life is the choice. Get full access to The Descent at chadprevost.substack.com/subscribe

    14 min
  3. Resentment, Avoidance, and the Work That Matters

    MAY 11

    Resentment, Avoidance, and the Work That Matters

    If you finish a paying assignment and feel, instead of relief, a kind of dull resentment — this episode is for you. Or if you sit down to the work that's been pulling at you for years, and the dishes suddenly need doing, the bills suddenly need paying — this is for you, too.Episode 4 of The Difficulty starts the Field Guide series with the foundational difficulty: the work that pays and the work that matters. They're not usually the same work, and most of us pretend they are.In this one I get into the years I spent writing trade journalism in freight and logistics — the compromises that taught me a lot but weren't the calling — and the friends who got the holy-grail book deal and discovered that "making it" was the start of a different grind, not the end of one. Plus Mark Fitten's $10K-publicist-and-NYT-ad story. The Norman origins of the word "courage." And why being 53 doesn't mean you've missed your window. At least I hope not.The challenge at the end: this week, make one move that matters. Even 90 minutes. Notice the resistance. Notice the breaking through.—CHAPTERS00:00 Resentment and Avoidance00:46 Show Format and Big Question02:45 Work That Pays vs Matters04:11 Compromises and Day Jobs06:03 What Is Your True Calling08:37 Renew Commitment and Habits12:10 The Hidden Work After Creating17:31 Choose Courage Over Ambivalence22:54 Time Is Longer Than You Think26:05 Your Work Matters Closing—FREE — THE DIFFICULTY FIELD GUIDEEight difficulties every working writer faces, and what to ask when each one shows up.→ crossroadspublishing.group/assets/pdfs/The_Difficulty_Field_Guide.pdf—WHERE TO FIND MESubstack — new essays Wednesdays, the Working Publisher news digest Fridays, weekend essay readings Saturdays→ chadprevost.substack.comThe Difficulty — Monday (the why), Thursday (the how), Saturday (essay readings) — wherever you listen to podcasts→ chadprevost.com/the-difficultyCrossroads Publishing Group — publishing services, IF/THEN Books, the Iris Blackwood mystery series→ crossroadspublishing.group—Thursday: three things that happened in publishing this week and what they mean if you're building toward a direct audience.The difficulty in life is the choice. Get full access to The Descent at chadprevost.substack.com/subscribe

    28 min
  4. The Kind of Help that's Hard to Ask For, and the Kind of Help You Don't Know You Need

    MAY 9

    The Kind of Help that's Hard to Ask For, and the Kind of Help You Don't Know You Need

    I almost drowned on the Ocoee River. The thing that saved me wasn’t anything I’d thought to ask for. This is the first essay in the Saturday series at The Difficulty — longer pieces from a series I’ve been writing on Substack called The Descent, about the choices that shape a creative life. Saturday is for the essays that don’t fit the news-cycle pace of the rest of the week. Today’s is about how hard it is to ask for help — and the deeper, harder thing underneath it: the surrender we resist for years before we know we’re resisting it. Drawing on David Whyte, David Hawkins, and Carl Jung’s “shoes too small” image, with a near-drowning story I haven’t told publicly before. Closing question: What am I holding onto that I already know isn’t working? — CHAPTERS 00:00 Saturday Series Intro 01:01 The Hard Word — Help 03:26 The Near-Drowning Lesson 04:52 Two Kinds of Help 06:52 Surrender vs Giving Up 07:57 Shoes Too Small 09:40 Letting Go Changes You 10:46 Readiness and Courage 12:55 Modern Ways to Give Up 14:47 The Question to Ask 15:07 Closing and Where to Find More — FREE — THE DIFFICULTY FIELD GUIDE Eight difficulties every working writer faces, and what to ask when each one shows up. → crossroadspublishing.group/assets/pdfs/The_Difficulty_Field_Guide.pdf — WHERE TO FIND ME Substack — new essays Wednesdays, the Working Publisher news digest Fridays → chadprevost.substack.com The Difficulty — Monday (the why), Thursday (the how), Saturday (essay readings) — wherever you listen to podcasts → chadprevost.com/the-difficulty Crossroads Publishing Group — publishing services, IF/THEN Books, the Iris Blackwood mystery series → crossroadspublishing.group — “The difficulty in life is the choice.” Get full access to The Descent at chadprevost.substack.com/subscribe

    16 min
  5. Get Over Yourself and Learn as You Go

    MAY 7

    Get Over Yourself and Learn as You Go

    Episode 2 of The Difficulty. The hardest thing about indie publishing isn't writing the book. It's giving up the fantasy that the book will market itself. In this one I get honest about the ego defenses we run as creators when it's time to put work into the marketplace — the survivorship bias of the "no marketing" success stories, the isolation that breeds false certainty, the asymmetric gap between making (which feels like magic) and marketing (which feels like math). Some of what comes up: — Howard Finster on his farm. Emily Dickinson and her response to Thomas Higginson. Fernando Pessoa's 200 heteronyms in a Lisbon trunk. — The German musician who poured everything into one album, got profoundly little response, and stopped. — My own Iris Blackwood cover that got 14 thumbs up and 38 thumbs down on NetGalley — and what to do with that. — "We haven't failed. We just haven't found our audience yet." The challenge at the end: pick one marketing lane, commit to it for 30–60 days, and report back. If the show is doing something for you, the easiest way to support it is to share this episode with one person you think it'd land for. Or restack the post. Or both. Episode mentions: — The Difficulty Field Guide (free PDF — eight difficulties every working writer faces): https://crossroadspublishing.group/assets/pdfs/The_Difficulty_Field_Guide.pdf — Iris Blackwood and the Curse of Hemlock Island, just out at IF/THEN Books — extras page (Decision Tree map + reading guide): https://crossroadspublishing.group/if-then-books/hemlock-island/ New episodes Mondays (the why) and Thursdays (the how). The difficulty in life is the choice. Get full access to The Descent at chadprevost.substack.com/subscribe

    42 min
  6. The In-Between Is the Hard Part

    MAY 4

    The In-Between Is the Hard Part

    The very first episode of The Difficulty. A 50-year-old paperweight on my father’s desk turned out to be a line from a 1900 Irish play, and the seed of this show. What you’re getting on Mondays vs. Thursdays, what’s launching this week at crossroadspublishing.group, the founding-and-selling of C&R Press, the Terminus Magazine “just make it real” lesson, and the $4,000 bestseller campaign I almost said yes to two days ago. 00:00 Welcome — we’re not about perfectionism, we’re about idealizing 03:00 The motto: the difficulty in life is the choice 04:30 Origin of the quote — my father’s rock paperweight, George Moore, 1900 08:00 What this show is NOT (and is) 11:30 The free Difficulty Field Guide 12:30 What’s launching this week: the show, the site, IF/THEN Books, Iris #1 17:00 Crossroads Publishing services — for writers with a body of work 20:00 Who I am — PhD, ICF coach, Enneagram, C&R Press 1996-2015, 50+ books 24:00 Making it real imperfectly — the Terminus Magazine origin story 30:00 Who this show is for 33:00 The $4,000 Brody bestseller campaign and $2,000 Cohen Groundbreakers 38:00 The in-between is the hard part — the real difficulty isn’t the choice 42:00 What’s coming Thursday: how to stop believing your stuff is special The Difficulty Field Guide (free PDF — eight difficulties every creative life faces) Iris Blackwood and the Curse of Hemlock Island (launching Tuesday May 5, with free Decision Tree map and educator’s reading guide) Crossroads Publishing Group — IF/THEN Books, Crossroads Press services, free resources. Subscribe to The Descent (the show’s hub): YouTube: https://www.youtube.com/@chadprevostwriter Personal site: https://chadprevost.com Mentioned in this episode: - George Moore, The Bending of the Bough (1900) — the source quote - C&R Press (founded 2006, sold 2015) - Terminus Magazine (Atlanta literary magazine origin story) - Game Time Books — earlier interactive-fiction venture - Dave Chesson / Kindlepreneur — Publisher Rocket - Paul G. Brody / Brody Consulting — bestseller campaign service - Bryan Cohen / Best Page Forward — Groundbreakers community - Robert Frost — “the road less traveled” Get full access to The Descent at chadprevost.substack.com/subscribe

    44 min
  7. Trailer: Welcome to The Difficulty

    TRAILER

    Trailer: Welcome to The Difficulty

    Here’s the question this show keeps asking: What does it cost to keep choosing the work? This is The Difficulty — a podcast about the choices that shape a creative life, and the courage it takes to make them. I’m Dr. Chad Prevost — writer, publisher, ICF-certified coach. I’ve spent years inside the questions creative people actually wrestle with. Not the productivity-hack version. The real one. New episodes weekly. Full episodes, transcripts, and Notes from the cutting-room floor. Subscribe wherever you listen. The Difficulty. Start anywhere. Get full access to The Descent at chadprevost.substack.com/subscribe

    1 min
  8. Why Knowing Your Partner isn't the Same as Understanding Them (and How the Enneagram Helps)

    12/03/2025

    Why Knowing Your Partner isn't the Same as Understanding Them (and How the Enneagram Helps)

    In this episode, Chad, co-founder of Big Self School and part of the Leading Human podcast team, discusses the transformative power of the Enneagram in long-term relationships. He highlights the common communication pitfalls couples face and how understanding each other’s Enneagram types can facilitate deeper connections and growth. This episode also previews the upcoming Enneagram Couples Retreat on February 14th, 2026, in Chattanooga, designed to help couples understand their partner's core motivations and foster compassionate understanding. 00:00 Introduction and Welcome 00:47 Understanding Relationship Dynamics 07:59 The Power of the Enneagram 14:01 Enneagram for Couples Retreat 21:33 Conclusion and Call to Action If you're in Chattanooga this February, check out our Enneagram for Couples Retreat here. Early bird and 2 for 1 pricing while supplies last and ends December 17, 2025.We do trainings all over. We'll bring a communication workshop in person or online. https://bigselfschool.com/trainings Don't just take it from us, hear what others are saying: https://bigselfschool.com/testimonials. Book a chemistry call. Learn more about what we do, how we might support you, and if the fit is right: https://calendly.com/shelley-bss/disc... Get full access to The Descent at chadprevost.substack.com/subscribe

    22 min
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The Difficulty is a show about the choices that shape a creative life, and the courage it takes to make them. Hosted by Dr. Chad Prevost, writer, publisher, and ICF-certified coach. Each episode explores a real decision point: craft, courage, failure, reinvention, and the stubborn belief that the work is worth doing. New episodes weekly. Subscribe for full episodes, transcripts, and Notes from the recording cutting-room floor. chadprevost.substack.com

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  • Creator
    Dr. Chad Prevost
  • Years Active
    2K
  • Episodes
    265
  • Rating
    Clean
  • Copyright
    © The Descent
  • Show Website
    The Difficulty