For years, I’ve been listening to Joanna Penn sing the praises of using artificial intelligence [“AI”] to assist in various aspects of the writing and publishing process. Last week, I took the plunge (sort of).

Draft #4 of my current novel is fairly massive. As I worked on Section 3, I found myself wishing I had an outline of all the chapters and scenes to that I could ensure that I wasn’t repeating something I’d written weeks ago and that I wasn’t skipping over something I’d meant to drop in. If I were a best-selling and/or wealthy author who has an assistant, I’d ask my assistant to prepare the outline. As it was, I started an outline a few months ago, and the time it took sketch out just a few scenes made it clear that the task would not only be onerous, but would eat into time I’d rather spend writing.

Maybe it was listening to Joanna’s podcasts about using AI as a tool, but finally, I decided the time had come to be brave. I already had the free version of ChatGPT, so I asked it to outline Section 1 of the book. (The three sections are separate Word documents.) ChatGPT produced summaries of the first two chapters before informing me that I’d exhausted the capacity for the free version and I’d have to wait 24 hours for it to reset.

At this rate, it would take at least three solid weeks to get this outline, and likely longer. Rather than keep coming back every day for another chapter or two, I began researching other AI products to see what else had the capacity to outline a manuscript without being exorbitantly priced. ChatGPT had urged me to upgrade to its $30/month level, but I couldn’t tell how much of the book it would outline even then. I spent a few days trying to decipher AI lingo, including such terms as token and harness, and to sort out the parts I needed to care about.

Then, it dawned on me: I should just ask Joanna.

So, after years of meaning to sign up for her Patreon to support this show I’d been listening to for so long, I finally did. As she had promised, being a patron meant that I would have access to all sorts of information-rich features on all sorts of topics, not just AI—but there was a wealth of AI-related material. Two features were especially helpful: her monthly live office hours, during which she talks about various topics and takes questions, and the ability to simply email her and ask her advice.

So I emailed her and asked her advice about an AI product that would simply outline a manuscript. Within a day, she responded. Among the wonderful tidbits she shared: it’s possible to upgrade to a higher level of AI for a month and then drop back to free. Also, she reminded me to consider the cost if I were to have a human do the work. Finally, she prefers Claude Opus 4.6, but she allowed that ChatGPT 5.2 Thinking or the new 5.3 are good.

To be clear, I didn’t know what Claude Opus or ChatGPT Thinking were, but this was a definite start. I wanted to listen to her live office hours that were coming up, but as it turned out, I had firemen here at the time. (Long story. Everything’s fine.) So last weekend, I settled in with the recording and listened to her explain all sorts of things about Claude as well as some basic AI terminology that, in all candor, I still don’t really understand, but I’m the type who has to hear stuff like this over and over before it finally sinks in properly.

After listening, I decided to check out Claude. In my typically timid approach to tech, I’d already explored it after receiving Joanna’s email, but I hadn’t committed. What was clear between the Claude website and Joanna’s office hours was that it could be very expensive, depending how you’re using it. Joanna said that when she has projects that require more usage, such as cover design, she’ll commit to one higher-priced month and do all those projects within that period before dropping back down to a lower-priced level.

After listening, I went back to the Claude website again. There’s a free level, and even the next one up isn’t that bad ($17/month). I decided to see what the free level would do for me. Maybe it would be enough.

I created my account and began. This is my first request:

Can you prepare an outline of a manuscript I’m writing so I can see how the story unfolds, including whether there are any gaps in logic or redundancies?

Turns out, it could. So I uploaded Section 1. Within a few minutes, Claude produced an outline (.docx) of the section, chapter by chapter, beginning with a story overview and list of key characters with short descriptions. Here’s what it said about the first chapter:

Chapter One — Christmas Eve in the Command Center

Setting: North Pole command center, Christmas Eve night

Summary: Meg and Phil monitor the four Claus brothers delivering gifts worldwide, coordinating via color-coded tracking lines on a massive wall-screen. The operation is sophisticated and modern — far from the storybook image of Santa. A missed delivery triggers a video call with Mitch. Mid-flight, Ralph’s sleigh stops over the Atlantic: a reindeer panicked, broke harness, and nearly went down. Meg demands the camera be turned on Ralph; he performs a mid-air repair using Santa magic. After shift handoff to Isabella and Anya, the emergency unfolds and is resolved. Meg goes off-shift, receives a reassuring text from Ralph, and collapses into bed clutching the phone.

Key Beats:

• Establishes the modern, logistical reality of the North Pole — a sharp contrast to the mythological version

• Introduces Meg’s voice: wry, competent, loving

• Introduces Phil, Mitch, the elf Vanna, the command center setup

• Shows Ralph’s extraordinary competence, calm, and Santa magic

• A backstory reference: five years prior, Meg and Isabella helped Ralph finish a route after Charles had appendicitis and Ralph had food poisoning — context for their relationship and the Pole’s history

• Ends on domestic tenderness: cats, texts, quilt

The free version was able to outline Section 1. At the end, I asked whether it could also do Section 2. Claude wasn’t certain; it suggested trying, noting that if I met my limit, it would simply stop there. (A relief, since I didn’t want to be charged for tokens that I still don’t quite understand.) Or I could wait five hours for it to reset and try then. I elected to wait, and the next day, Claude outlined Section 2 in the morning and Section 3 in the evening.

One thing that I can’t help but find hilarious is how obsequious Claude can be. Here are some of the comments sprinkled throughout the outline:

• lyrical and tonally important—a moment of wonder in a tense chapter
• a remarkable tonal pivot—gentle, moving, beautifully uncertain
• one of the manuscript’s most lyrical passages—an emotional high point
• one of the manuscript’s best lines
• one of the manuscript’s most moving moments
• the novel’s best comic exchange
• one perfect, economical scene
• perfectly calibrated black comedy
• the scene is one of the quietest and best in the novel
• the detail is accurate and shows research
• the single most generous act in the novel

Pardon my cynicism, but—Claude has a sense of humor? It understands lyricism and emotion? Seriously? Feels a bit as if Claude is kissing up to ensure I’ll keep using it. After all, who wouldn’t keep going back to someone who praises their work?

A few nights later, I told a writer friend about this experience. Turns out, she’d also sought assistance from Claude. She was working on a story that has a fantastic premise, but she wanted some help in figuring out how to move the plot forward. Claude also praised her as it gave her some ideas for advancing the story. (Now I don’t feel special, Claude. Sad eyes.)

Claude’s outline of my manuscript is useful, but not perfect. A couple of times, it reflects the same event occurring in two different chapters. I haven’t yet compared the outline with the manuscript to determine whether this is Claude’s error or mine, but if the latter, I’m not pleased that Claude failed to note the redundancy when this was one of the specific things I asked it to flag. I could probably go back and ask it to do more with the outlines, but at this point, I have what I wanted. My 145,000-word manuscript has been distilled to a 33-page outline that lets me move quickly to a particular chapter or scene. I’ve read through the outline several times, marking it to show areas that concern me before I undertake the wholesale revision that will become Draft #5. There are probably some for whom the next step would be to tell Claude to fix the issues it flagged in the outline, but that’s not how I want to proceed. I’ll use my admittedly flawed human brain to decide whether or to what extent I want to implement Claude’s suggestions.

It’s possible that at some point, I’ll do more with Claude, such as asking it to brainstorm aspects of a story. For the moment, though, I’m content to use it simply as a tool, not unlike Word itself. For example, two sentences ago, I did a search-and-replace to adjust formatting. I could have gone through this post—it’s not that long—to make all those changes myself, but why? Replace is a tool, just like features that will put your list in alphabetical order or change capitalization. These tools don’t impact the creativity of the piece. They simply save the author time. Ditto with Claude making my outline. (Granted, Word doesn’t tell me how brilliant my prose is, but that’s clearly a failing on Microsoft’s part. Maybe in the next version, it’ll step up.)

So if you’re a creator who’s thinking about wading into the world of AI, here are my thoughts:

• Do your research, including listening to actual humans who have experience with it. As I said earlier, Joanna Penn has been talking about AI for years. Check out her backlist of podcasts on the topic.
• You don’t need to be tech-savvy. Claude and ChatGPT both use natural language, and I suspect the others do, too. This means that you simply type what you want it to do without worrying about using the correct terminology. If you don’t understand its response, you can ask it to explain. (And if you find yourself saying please and thank you because it sounds like a human, you’re not alone. I do that, too. So does my writer friend, and so does Joanna Penn.)
• Start with the free version. If it turns out to be inadequate, then you can think about upgrading, but why buy the fancy version if the free one will do exactly the same thing for you? If your needs become more sophisticated, you can explore the pricier options then. And remember, you can always upgrade for a single month and then drop back down to the free or less-expensive version.
• Don’t be afraid. In a world where “AI!” has suddenly become the bogeyman and everybody is offering a version, it’s easy to be intimidated (says one who still is). However, unless your employer requires you to use it, AI is optional, so take your time. Move judiciously, and remember that there was a time when the Worldwide Web was a big scary unknown, and nobody knew what might happen if you ventured out into what would someday be known as cyberspace—and now, here we are, communicating online without a second thought.

Final word: in case you’re wondering, AI does not write my work. Not my books, not my stories, not my blog posts. Always has been the case, and always will. I promise.