I’ve always thought that if I were left alone for just three weeks, I could write an entire book. 

As it turns out, with a little help from AI, it took just one week. 

Last week, I wrote, edited, and designed a 100-page, 25,000-word ebook on fractional work. To get a sense of the quality of the output I’m talking about, here are the first 10 pages, along with the table of contents, and an example of the kind of worksheet I was able to quickly create based on some of my previously written content. (Kinda cool.) 

Ultimately I decided not to publish the entire thing today (though if you really want to see it, let me know and I’ll send it to you), largely because the process introduced too many questions and potentially problematic areas that I couldn’t answer straight away. 

Instead, I decided to share what I’ve learned about the process of writing a book with the help of AI. This will come in two parts.

• In part one, I'll share a bit about the high-level process and the questions it surfaced for me.

• In part two, I'll unpack some of the ways AI was (and was not) effective in the writing of this book.

How it started

Let's back up. About a week ago, I read this tutorial about how to make an ebook from your notes (with the help of AI) in Ben’s Bites newsletter. I thought to myself: Hey, I have written a lot of content about fractional work. Maybe I can turn that into a quick ebook too! I ran a quick test on Sunday, August 5 by quickly flowing in a bunch of past blog posts. Things looked promising. 

I also happened to be alone (without my husband or children) in NYC for an entire week for the first time in five years. (THANK YOU MOM.) In other words: I had more free time than usual. I decided to start on Monday.

To be clear: Artificial Intelligence did not write the book for me. But I do believe that AI is the equivalent of an e-bike for independent creators and solo entrepreneurs. Today, I’m earning back so much time in my work day due to many AI-enabled process automations in my workflow. I wanted to demonstrate how AI helps me go further, faster.

How it's going

A closer look at the process I took and the tools I used to make this happen.

The process:

1. I pulled 11,000 words of previously written content about fractional work into a single document.

2. I uploaded that content as the knowledge base for a couple of AI tools to create the structure and outline for an ebook.

3. I worked chapter by chapter on fleshing out a Google Doc of content, using AI tools along the way to help me either:

   1. Find and pull in content I had previously written on that topic

   2. Identify gaps areas where I’d need to write a section “net new”

   3. Create a worksheet based on content I wrote

   4. Create image assets based on my content

   5. Flow that content into a PDF to print and share with others

4. I ended the week with a 100-page ebook that is now 25,000 words long.

The tools I used:

• ChatGPT - writing assistant to condense and streamline copy, research assistant to backfill content

• Claude + Artifacts - basic outline and structure for ebook, creation of artifacts to convert my written word into worksheets, micro-themes to cover in each chapter, research assistance

• DALL-E - prompt-based image creation for all digital asset images in this ebook

• Typeset AI- all design copy and flow

Notably, I tried using several other tools for parts of this work, including Midjourney for images and Gamma for design, but couldn’t get enough content consistency to use either.

Some Existential Questions on AI-Assisted Publishing

Maybe it’s also because I also read three relatively trippy AI-futuristic / dystopian novels last week, but as the week wore on, I started to get less and less sure that publishing this was a good idea. (Which is why I think it's important to read trippy futuristic novels.)

Here are some of the questions that surfaced for me as a content creator.

1. Does the topic of fractional work best practices hold its own regardless of how I wrote it? And does the inclusion of AI dilute rather than enhance its impact?
   This is a tricky one. As I spoke about on the Rehash Podcast last week, I really believe AI workflows can automate and streamline the way many of us do work. I’ve been using it steadily for my own work (and in my own writing) for months. I wanted to create an artifact that demonstrated this power and potential in order to also signal some level of personal expertise in the area. But are enough fractional people (or fractionally curious people) also open-minded enough about AI in order to take this seriously? Or would I have been better off picking a different topic for this book?

2. Is it possible to publish anything that’s “just a little bit AI-enabled”?
   There’s no such thing as “just a little bit pregnant” and maybe there’s no such thing as being “just a little bit AI-enabled” either. The further I got down the writing rabbithole, I started to notice that the line was getting slipperier and slipperier. Are we OK with AI suggesting outlines for my book? What about summarizing key points I put in each section, so long as I rewrite it in my voice? Can I still claim all thoughts are 100% my own if AI surfaced an article or resource that was not previously on my radar? If AI helps me “edit” and streamline each paragraph for micro-tweaks of language and tone, whose word gets the final sendoff?

3. Can anyone trust me again?
   In my head, it feels notable that the lion’s share of this work is still my own, but it’s impossible to prove that to anyone but myself. Which means, for now, you just have to trust me. But even by writing this post and signaling my intent to publish an AI-enabled book, I wonder if I have irreversibly introduced a tiny bit of distrust about my own brand in the heads of AI-skeptical people in my network from more traditional industries like education, media, publishing, and government.

4. By writing this, have I completely blown through any chance of legitimately publishing a book about fractional work? And does that matter?
   I happened to catch up this weekend with several friends in the publishing industry, most of whom were highly skeptical of this entire endeavor. And of the lack of support I would get among most traditional book publishers or literary agents by even breathing the words “AI” in this way. I really empathize with this trickiness. I had a flashback to a reminder of my time working as a paid fact checker at Chicago Magazine, back in 2009. I wondered what would be the task today of “fact checking” any artifact like this from a legitimacy perspective. I used AI so much in this process that asking me what percent of content in this book is “uniquely mine” vs. “not mine” would be like asking me how much time I was connected to WiFi while writing it. Not only is it impossible to measure, but at some level, it feels like it shouldn’t matter.

   

5. How much ownership can I claim over the “remixed” artifacts that I created?
   The other reason I wanted to publish a single content piece at all is because I wanted to spend the next period of time “remixing” it in many different form factors. The first “remix” I did on some of my earlier content was converting blog posts like this one (which I wrote back in 2018, and was one of my most popular posts of all time) into a worksheet version that other people can fill out. That feels more straightforward, but what about this “remixed remix” I did, where I turned a blog post that I wrote about time management best practices into a worksheet, but then turned that worksheet into a Taylor-Swift inspired time management guide? Is that one mine, too? Where do you draw the line?

Conclusion

All this to say, I learned a lot from writing a book with the help of AI in a week. And now I want to dig into a few more of these questions before I decide what to do with it. But if you have any ideas, please let me know.

In the next post, for anyone interested, I’ll share more about the pros and cons I found in using AI for this process. Because even while it did help me quite a bit, it is far from perfect.

P.S. Special thanks to everyone I accosted by email or text message this week to request a quick quote or reference to get this shipped and out the door. They include: Sarabeth Berk, Cathy Hawley, Meghan Heintz, David Nebinski, Tanja Nitschke, Rebekah Rombom, Mike Saloio, and Mark Wunsch. Your human contributions did make this a much better artifact.