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

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.

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...

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 seri...

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.

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...

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 o...

In Dante’s Inferno, the lustful are not burned. They are swept, a great relentless wind moves them endlessly, helplessly, no footing, no direction, just the next gust carrying them where it will. This week’s episode is a weekend reflection; slower, more meditative, less about publishing and craft and more about the soul-work questions underneath. Lust in its oldest, broadest sense—unrestrained wanting. The fire the Greeks understood. The Cyclops’s single eye. Odysseus making himself Nobody to escape the cave. Emily Dickinson’s delight in being Nobody too. And the difference between failure (which you can face) and self-a...

Topics covered:

A field report from week one of Crossroads Publishing Group—what’s coming in the door, what’s surprising, what’s confirming.

What a hybrid press actually is. A working definition: a publisher where the author shares the financial risk via a fee (broadly $5K to $45K, depending on the engagement), in exchange for real editorial work, professional production, distribution under the press’s imprint, and a higher royalty share than traditional contracts.

Why the vanity-press confusion exists, and why it’s no longer accurate to the category as it stands in 2026.

Brooke Warner, the founder of She Writes Press, gave a TED talk in 2017 called “Green-Lighting Yourself” that I have been thinking about for years. The argument: the traditional creative industries, publishing and film and music, have shifted toward green-lighting only artists who are already famous or who have celebrity connections. The writers and filmmakers and musicians who refused to wait for those industries to discover them, who chose to publish or produce their own work without permission, have a name. Warner calls them green-lighters.

The line from her talk that I cannot let go: “Legitimacy cannot be bestow...

When I was seventeen, I drove my parents’ conversion van home from a party with a six-pack in my system and a freshly-dented bumper on a stranger’s parked car. The officer who arrived at our house decided not to charge me with driving under the influence. He told me to go inside and sleep it off. I have thought about that night for thirty-five years.

This episode is an essay reading. The material is personal. Three stories from my reckless adolescence in Richmond, Virginia, told plainly. The drinking and driving. The LSD afternoon at a Goochland Coun...

This week, two things in one episode.

I sit down with Andrew Najberg, novelist, poet, editor at Symposium Magazine, co-owner and co-editor-in-chief of Aethon Books: Wicked House, college teacher, husband, father, and my Chattanooga neighbor. Andrew has five novels out, including The Mobius Door, Golotok, The Neverborn Thief, and Eat the Light, which dropped last month from Wicked House. He has two poetry collections out, with Paradise Falls forthcoming.

What I wanted from this conversation was to understand how Andrew actually does the work. Day to day. Hour to hour. We talk about:

...

In 1917, Virginia and Leonard Woolf set up Hogarth Press in their dining room with about forty pounds of operating capital. Five years later, Sylvia Beach published Ulysses from a Paris bookshop after every major publisher refused it. A few months after that, Hogarth Press published The Waste Land — another book the corporate houses had passed on. In a span of five years, two small presses founded by writers and bookshop owners redefined what English-language literature could do in the twentieth century.

The publishing moment we are living through in 2026 looks remarkably like that one. The big houses ha...

Scott Bedgood started his career covering Little League games at the Tyler Morning Telegraph in Texas. Now Scott is a journalist, author, content marketer, and clean-comedy stand-up opening at The Ryman in just a few days.

This is the first interview episode of The Difficulty, and Scott is the right writer to launch the format with. His through-line is storyteller, and the way he’s threaded that line — from sports journalism through self-publishing Lessons from Legends (interviews with twelve College Football Hall of Fame coaches including Barry Switzer, Steve Spurrier, and Tom Osborne) into a stand-up comedy care...

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 adaptat...

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 sett...

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 jour...

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 yea...

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...

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 — m...

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.

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 Co...

In this podcast episode, Chad Prevost, executive coach and co-founder of Big Self School, delves into the fundamentals of building trust within organizational teams. Chad highlights common communication mistakes that erode trust, such as making vague requests, assuming commitment when it hasn't been clearly given, and handling feedback poorly. He explains the importance of clear, committed communication and outlines a six-element framework for making effective requests, including the necessity of naming the timeframe and conditions of satisfaction.

Chad offers strategies for constructive feedback through the SBIA framework (Situation, Behavior, Impact, Ask), emphasizing the importance of daily conversations...

In this episode of Leading Human, host Chad welcomes leadership expert and author Jim Karloff to discuss his book, 'The Six Pillars of Effective Leadership: A Roadmap to Success.' Jim shares his journey in leadership, the inspiration behind his book, and how the six pillars—compassion, empathy, stability, focus, humor, and the crucial element of integrity—can be effectively implemented in any organization. Tune in to explore the nuances of these pillars, learn from Jim's professional experiences, and gain insights into building a resilient, people-first team in today's rapidly changing world.

00:00 Introduction to Jim Karloff and His...

In this episode of Leading Human, we sit down with David Spinks, a renowned community builder, coach, and storyteller, to explore his journey of cultivating resilience, belonging, and inner alignment. From founding CMX to dealing with burnout and anxiety, David shares his personal experiences and insights on finding enoughness and leading with heart and clarity. Tune in to hear about his transition from a high-achievement culture, dealing with personal crises, and the importance of authenticity and alignment in leadership. Learn how to navigate challenges, balance ambition, and tap into clean fuel to create meaningful impact in your life and...

Join us in this episode of Leading Human as we delve into the importance of team norms, emotional intelligence, and collaborative culture with Vanessa Drucker, author of 'The Emotionally Intelligent Team.' Discover how the right practices can transform team dynamics, optimize interactions, and enhance performance. Vanessa shares insightful stories and practical steps on building psychologically safe and emotionally intelligent teams. Make sure to watch this episode to learn the secrets of high-performing teams and how to implement them in your organization.

00:00 Introduction to Emma AI and Today's Guest

00:36 The Power of Team-Based Tools

Pankaj Singh is a leadership strategist and founder of Singh Leadership, where he helps high-achieving professionals transform burnout into clarity and purpose using neuroscience-informed frameworks like the Purpose Factor

If Leading Human is where emotional intelligence meets organizational impact, then Pankaj Singh is your kind of guest. A former C-suite leader who began his journey training under a lama, Pankaj now empowers leaders to transform reactive pressures into purpose-driven presence.

In this episode of 'Leading Human', Chad welcomes Pankaj Singh, a leadership strategist and founder of Singh Leadership, to discuss turning stress into strategic clarity, the r...

In this episode of 'Leading Human,' host Chad Prevost sits down with Dr. Eva Selhub, a Harvard-trained physician and bestselling author, to explore the intersection of cutting-edge neuroscience and ancient wisdom.

Dr. Selhub shares her journey from conventional medicine to studying resilience and the mind-body connection after a life-changing experience. They discuss the importance of emotional intelligence, stress management, and creating healthy habits for leaders. Dr. Selhub outlines six pillars of resilience and provides practical tips on how to translate scientific understanding into everyday practices that enhance performance and well-being.

The conversation also delves...

In this episode of Leading Human, host Chad interviews Radhika Dutt, author of 'Radical Product Thinking' and the forthcoming book 'Escaping the Performance Trap.' Dutt challenges the conventional wisdom of goal-setting in performance management, arguing that tools like OKRs and KPIs often backfire.

Instead, she introduces an alternative framework focused on detailed vision statements, puzzle setting, and puzzle solving, which encourages continuous learning and adaptation. The conversation explores the history of goal-setting, its limitations in complex environments, and practical steps for implementing Dutt's approach.

Author of Radical Product Thinking, a speaker and entrepreneur, Radhika...

In this episode of Leading Human, host Chad converses with Jen Mueller, a seasoned sports broadcaster, leadership coach, and host of Talk Sporty to Me.

Jen shares her unique experiences of interviewing athletes while cooking, and how these interactions reveal vulnerability and human connection. The discussion delves into critical leadership communication strategies, emphasizing the importance of timely, clear, and meaningful feedback.

Jen draws parallels between leadership in sports and business, highlighting the role of clear objectives and the nuances of giving accurate praise and constructive feedback. She also provides actionable advice on preparing for and...

In this episode of 'Leading Human,' host Chad Prevost welcomes Scott Allen, a seasoned leadership development strategist, certified emotional intelligence coach, and Enneagram teacher. Scott delves into his book, 'The Enneagram of Emotional Intelligence,' which correlates the nine Enneagram types to core EQ skills, offering a pathway to radical self-awareness. The conversation explores Scott's insights on how integrating the Enneagram with emotional intelligence can lead to profound personal and professional growth, highlighting the importance of self-awareness in leadership. Chad and Scott also share personal anecdotes and practical advice for embracing emotional awareness to enhance decision-making, relationships, and...

In this episode of Leading Human, Chad sits down with EQ-research pioneer Joshua Freedman.

Who’s our guest?

Why listen?

In the final episode of the Leading Human series about Enneagram type communication dynamics in the workplace, we explore the interactions between Types 8 and 9. The episode delves into the synergies of these neighboring body types, highlighting how their partnership can merge strength with diplomacy and balance leadership with harmony. It also discusses potential conflicts arising from their differing paces and decision-making styles, offering practical strategies for nines to voice their needs and for eights to practice patience. The episode aims to enhance emotional intelligence, promote psychological safety, and provide actionable insights for effective communication and teamwork.

00:00 Introduction...

In this episode of Leading Human, we conclude our series on Enneagram type-to-type communication dynamics in the workplace by focusing on the interaction between Type Seven and Type Nine. We explore how these types can create a harmonious working relationship, highlighting their strengths and synergies as well as the challenges they might face. Practical communication tips are offered to help tailor strategies to building trust, achieving higher emotional intelligence, and ensuring psychological safety. Specific advice includes setting clear deadlines, involving both types in decision-making, proactive communication, and leveraging each other's strengths for optimal team performance. The episode emphasizes the...

In this episode of 'Leading Human,' the focus is on understanding the communication dynamics between Enneagram Type 7 and Type 8 in the workplace. Broadcasting from Common House in downtown Chattanooga, the episode explores the high-octane interaction between these energetic types. It covers their strengths, such as Type 8's assertiveness blending with Type 7's creativity, and synergies like their shared love of independence. The episode also delves into potential conflicts, addressing issues like control versus freedom and different emotional responses. Practical tips are offered on managing these dynamics effectively, emphasizing the importance of open, respectful communication and leveraging each type's...

In this episode of Leading Human, we delve into the Enneagram type-to-type communication dynamics, focusing on how Type Nine and Type Six interact in the workplace. We explore the synergies between these types, emphasizing how their complementary styles can create a stable and secure environment. The discussion covers potential conflicts, including decisiveness issues and energy mismatches, and offers practical strategies to mitigate these challenges. Listeners are encouraged to implement frameworks and communication techniques to enhance trust and efficiency within their teams. The episode also calls for listener feedback to share their effective team communication practices.

00:00 Introduction to...

In this episode of Leading Human, the focus is on the communication dynamics between Enneagram Types 6 and 8 in the workplace. Hosts discuss how these two types, known for their loyalty and concern for security, can form a powerful team when trust is established. The episode delves into the natural synergies, potential conflicts, and practical strategies for building and maintaining trust between Type 6 and Type 8 individuals. It highlights the complementary strengths of each type and offers tips for fostering effective collaboration, making it an invaluable resource for anyone looking to enhance workplace relationships using the Enneagram framework.

00:00 Introduction...

In this episode of 'Leading Human in the Workplace,' we dive deep into the communication dynamics between Enneagram types 6 and 7. These 'head types' each manage fear and anxiety in different yet complementary ways—type 6 with caution and planning, and type 7 with optimism and exploration. Despite their differences, this pairing can create a balanced and dynamic partnership rooted in mutual trust, empathy, and support. The episode offers practical strategies to blend the strengths of both types, enhancing emotional intelligence and psychological safety within the workplace.

00:00 Introduction and Series Overview

01:34 Type 6 and Type 7 Dynamics

02:09 Co...

In this episode of Leading Human, we explore the interaction dynamics between Enneagram Types 5 and 9 in a professional setting. Host dives into their strengths, synergies, and challenges, offering practical tips for communication, leadership, and conflict resolution. By understanding how these types complement each other and addressing their passive tendencies, teams can achieve effective collaboration and decision-making. Tune in to learn how to foster trust, emotional intelligence, and proactive communication between Type 5s and Type 9s in the workplace.

00:00 Introduction to Enneagram Type Communication

00:13 Overview of Type 5 and Type 9 Dynamics

02:44 Strengths and Synergies of...

In this episode of 'Leading Human,' we delve into the communication dynamics between Enneagram Type 5 and Type 8 in the workplace. Explore how these two distinct types—Type 5 strategic thinkers and Type 8 decisive leaders—complement and challenge each other in leadership, conflict resolution, team collaboration, and more. Discover the synergies and potential conflicts of this pairing, along with practical communication strategies to foster greater psychological safety and effectiveness. Whether you're a newcomer or a regular listener, this episode provides high-level insights to encourage better communication and stronger team dynamics.

00:00 Introduction to Enneagram Communication Dynamics

01:03 The Unex...

This episode of Leading Human focuses on the communication dynamics between Enneagram types 5 and 7 in the workplace. The discussion covers how these two head types interact, their respective strengths, synergies, and the potential challenges in leadership, conflict resolution, team collaboration, and feedback. Practical tips are provided for improving communication, such as establishing processes and pacing, leveraging each type's strengths, and fostering mutual respect. The goal is to help create a work environment where both types can contribute meaningfully to innovation and project success.

00:00 Introduction to Enneagram Type Communication

01:45 Overview of Types Five and Seven