Writer’s block and the power of conversation

I talk to authors about writer’s block all the time. It’s a common problem, but the causes are deep and psychological. Both practical solutions and emotional support can be helpful.

I’ve written extensively about writer’s block. That’s what makes it a good test case. Could a chatbot trained on all that content provide the right combination of emotional support and practical advice?

Check out this conversation about writer’s block. What do you think?

Here’s a conversation between me and the Bernoff Book Coach. If it was you that was stuck, do you think it would help? In the text below, the bold italic are my questions, and the rest is the answers from the Bernoff Book Coach.

I have a terrible case of writer’s block. What can you suggest to get me unstuck?

What are the main causes of writer’s block?

Based on my experience with hundreds of authors, writer’s block has three main causes – and they’re all about what happens before you write, not during.

1. Insufficient Planning

This is the #1 cause. As I explain in Build a Better Business Book, writer’s block is the result of failing to have a plan before writing. When you sit down without knowing what to write, nothing comes out. It’s painful.

The solution: Before you start any chapter, determine a chapter objective – after reading this chapter, what will the reader know or be able to do? Then arrange your ideas, stories, arguments, proof points, and advice into a fat outline that tells a story.

2. Inadequate Research

You can’t write what you don’t know. As I describe in my post on there is no such thing as nonfiction writer’s block, if you doubt yourself or feel stuck, it’s often because you haven’t done enough research or talked to enough people.

The fix: Speak with others, dictate your ideas aloud, or interview people. You’ll realize you have more to say than you thought. Curiosity and colloquy cure writer’s block – talking to people and finding things out generates the fuel for writing.

3. The Procrastinate-Panic-Pray Process

This toxic pattern creates writer’s block by design. As I detail in my post on taming your writing process:

• Procrastinate: Put off writing until the last minute
• Panic: Realize you’re missing information and get frustrated
• Pray: Hope reviewers don’t blow up your rushed work

Every time you sit down to write, you realize you’re still missing information. That’s not writer’s block – that’s a broken process.

The Real Pattern

Notice what’s missing from these causes? Writer’s block isn’t actually about writing. It’s about preparation. You cannot be a writer without curiosity and without doing the groundwork.

The answer is never staring at a screen while your mind races aimlessly. Get out there, do the research, make the plan, and then writing becomes simply turning your outline into prose.

I keep trying to write but make lots of false starts.

False starts are actually a sign you’re skipping crucial steps in the writing process. Let me explain what’s really happening and how to fix it.

You’re Writing Too Soon

As I explain in Chapter 16 of Writing Without Bullshit, solving writing problems requires four ingredients: hard work, failure, relaxation, and time. False starts happen when you try to write before you’ve done the hard work of figuring out what you’re going to say and how you’re going to say it.

Your brain needs to work on the problem before you start drafting. When you jump straight to writing, you’re asking your conscious mind to solve problems that need subconscious processing time.

The Fat Outline Solution

Here’s the key insight from Build a Better Business Book: You can make yourself immune to writer’s block by creating a fat outline first.

A fat outline isn’t just bullet points – it’s your research, ideas, stories, arguments, and proof points arranged into a logical flow. When you have this scaffolding, you’re not staring at a blank page wondering what to write. You’re simply fleshing out notes into text.

As I describe in my post on fat outlines, writing down little notes and moving them around doesn’t trigger the “what if this sucks” anxiety that causes false starts. If you’re having trouble even with a fat outline, that’s useful information – it probably means you don’t have enough material yet.

Give Your Brain Time to Work

From my post on writing away from the keyboard, here’s what actually works:

First, create your outline or take a first shot at organizing your material. Get stuck if you need to – that’s actually an essential step.

Second, step away. Don’t keep banging your head against it. Meet with colleagues, take a walk, watch TV. Your brain will continue working on the problem subconsciously while you’re doing something else.

Third, give yourself time. If your writing is due Thursday, start outlining on Monday. You can’t rush this process. Your mind needs space to turn over possibilities and ideas.

The Real Problem Behind False Starts

False starts usually mean one of two things:

1. You haven’t done enough research – You’re trying to write about something you don’t fully understand yet
2. You haven’t planned the structure – You don’t know where you’re going, so you keep changing direction

The solution isn’t to try harder at writing. It’s to stop writing and go back to planning and research. Challenge yourself to find the right content and organization before you begin drafting.

Once you have a solid fat outline based on thorough research, those false starts disappear. You’ll know exactly what you’re writing and why – you’re just turning your organized notes into prose.

I worry that my writing is so bad that even an editor couldn’t help me.

That’s a fear I hear often, and I can tell you with confidence: it’s almost never true. Here’s why.

Good Editors Work With All Skill Levels

As I explain in my post on working with a developmental editor, a developmental editor’s job is to identify problems at every level – from your main idea down to individual sentences – and suggest fixes. That’s exactly what you need if you’re struggling with your writing.

The key insight: An editor doesn’t just fix your words. They help you understand why problems exist and how to solve them. This means you actually learn and improve through the process.

What Makes Writing “Bad” – And Fixable

From my experience doing close reads of manuscripts, here are the common problems I find:

• Muddled ideas
• Wordiness and redundancy
• Unclear structure
• Buried ledes (not getting to the point quickly enough)
• Over-reliance on paragraphs instead of diverse elements
• Inconsistencies in tone, tense, or voice

Notice something? These are all fixable. None of them mean you’re a hopeless writer. They mean you need guidance on how to organize and express your ideas more effectively.

The Real Question Isn’t Skill – It’s Readiness

The question isn’t whether your writing is “too bad” for an editor. The real questions are:

1. Do you have something valuable to say? If you have expertise, insights, or a story worth telling, an editor can help you express it.
2. Are you willing to do the work? As I describe in my post on the 7 levels of editors, good editing requires collaboration. The editor identifies problems and suggests fixes, but you must be willing to revise and improve.
3. Have you done enough research and planning? If you’re struggling because you haven’t done the groundwork – research, interviews, outlining – then you need to do that work first, not hire an editor yet.

What You Should Expect From Editing

From my advice to first-time editors (which applies equally to authors working with editors): The editor stands in for the reader and helps you be the best version of yourself. They don’t replace your voice – they help you express it more clearly.

A good developmental editor will:

• Challenge your main idea to make it stronger
• Restructure your content for better flow
• Point out where your expertise has created blind spots for readers
• Rewrite problematic passages and explain why the new version works better
• Help you understand the why behind writing problems so you can avoid them

The Bottom Line

If you’re worried your writing is too bad for an editor, that actually suggests you’re self-aware enough to recognize you need help – which is exactly the right mindset.

The writers who truly can’t be helped are the ones who think their first draft is perfect and refuse feedback. That’s not you.

Your job is to have something worth saying and be willing to work on improving how you say it. The editor’s job is to show you how. That partnership works regardless of your current skill level.

Which is more important when counseling a person with writer’s block, encouragement or practical advice?

Both matter, but practical advice is more important – and here’s why that’s actually the most encouraging thing I can tell you.

Why Practical Advice IS Encouragement

When someone has writer’s block, empty cheerleading doesn’t help. Saying “You can do it!” or “Just believe in yourself!” leaves them still stuck, staring at a blank page.

What actually helps people feel better? Showing them exactly what to do next. That’s real encouragement because it gives them a path forward.

As I explain in my post on therapy for prospective nonfiction authors, my job is to figure out people’s problems and recommend the best course of action for where they personally are in their journey. Like any good therapist, I ask questions intended to make them think carefully about where they are and what their next steps should be.

The Emotional Reality of Writing Problems

Here’s something I learned from reading Lawrence Weinstein’s Grammar for a Full Life: there are emotional reasons behind the writing choices people make. As I note in my review, while I focus exclusively on effectiveness for the reader, Weinstein examines the emotional qualities of different writing techniques.

This taught me something important: Understanding the emotional reasons behind writer’s block doesn’t mean coddling the writer. It means giving them tools that address both the practical AND emotional aspects of the problem.

What Actually Helps People Move Forward

From my 10 resolutions for writers, here’s what makes the difference: Go from editor to teacher. Don’t just tell someone what’s wrong – have a conversation about how your suggestions will make them better. Make writers better, and they’ll love you for it.

That’s the balance: practical advice delivered in a way that helps people understand why it works and how it will help them succeed.

The Most Encouraging Truth

Here’s what I tell blocked writers, and it’s both practical and encouraging:

Writer’s block isn’t a writing problem – it’s a preparation problem. That means:

• You’re not a bad writer
• You don’t lack talent
• You just skipped some steps

Once you understand that, the solution becomes clear: create a fat outline, do your research, give your brain time to work on the problem away from the keyboard. These aren’t just techniques – they’re proof that you CAN solve this.

My Approach

When I work with authors, I’m direct about what needs to change. But that directness IS the encouragement, because it shows I believe they can do better work. I wouldn’t waste time giving detailed advice to someone I thought was hopeless.

As I say in Writing Without Bullshit, my Iron Imperative is “treat the reader’s time as more valuable than your own.” When applied to counseling writers, this means: don’t waste their time with vague encouragement. Give them specific, actionable advice that respects their intelligence and their potential.

The most encouraging thing you can tell a blocked writer is exactly what they need to do to get unstuck. That’s not cold – that’s respect.

The power of conversation

There’s a widely accepted concept that all LLMs do is to assemble words in the pattern that most mimics what they’ve been trained on. But when you work with one, you begin to see that it goes further than that.

LLM-based tools like the Bernoff Book Coach don’t just regurgitate what they’ve been stuffed with. They find links between concepts and bring them to bear on the problem. The organize content into appropriate advice. And they address context. That’s something that no static collection of text can do.

It doesn’t matter whether a coach like this actually has empathy (because of course, it doesn’t). What matters is whether it can bring its knowledge to bear in a way that helps people. It seems like it can. And it’s only going to get better.

I’m really glad that I put all this knowledge into a single tool. And the next time I get stuck, this conversational bot is the place I’ll start in looking for solutions.