✍️ Tools to leverage AI as a writing partner (not a crutch)

🔘 Plus poll results on how you're feeling about the state of your businesses lately

Happy Friday, Free Timers! 🎉

We’re all about setting time free through smarter systems, so I don’t have to tell you about how helpful AI can be for certain parts of the writing process, whether you’re drafting a newsletter, tackling a personal essay, or going all-in on a book. But it’s not necessarily helpful for every stage.

The one thing AI can’t do is be you—an authentic, imperfect messenger, telling your stories and lessons learned with your unique spin. As Free Timer Kyle Wood puts it, “How can I really cultivate my voice, not the best or most correct voice?”

To see where AI can plug in, let’s break “writing” down into its many stages:

• Harvesting ideas, gathering inspiration from reading others’ work, and collecting your own personal stories

• Thinking, doing the harder work of synthesizing your take on those inputs

• Outlining (if needed; AI is superb at this)

• Writing, where you season the work with your unique voice while deepening your thinking. (AI can help you expand here, but it’s terrible at replacing this stage)

• Editing and revising (overall structure, tone, clarity, punctuation, punching up description, etc. — don’t miss

  Jeremy Caplan
  ’s prompt for this!)

• Polishing and finally, publishing!

There was enough cliché spammy click-bait cOntEnT on the internet before AI was everywhere, now we have terms for the inbound tsunami like slop and gruel.

It’s important to know where you stand when it comes to AI’s involvement with your writing and thinking—and what intellectual muscles you’re willing to let atrophy in favor of its alluring speed and (seeming) ease.

I do not use AI to draft newsletters or essays—I find the output banal, and I miss out on the best part: writing to explore and unearth what I think, especially the deeper layers and connections that I don’t make until I’m writing.

I’m sharing a list of my favorite resources below, but first, as promised from last time:

🔘 Our poll results from the previous 💌 TWS:

Are you surprised by these results, or do they sound close to your conversations among friends?

I’m sending love to the 41% of you (within those who answered) who are in full-blown meltdown or hanging on by a thread—you are not alone, and you’ve got this!!

🎧 I created this podcast playlist on Spotify just for you »

✍️ My Favorite Tools for Supporting Your Writing

In her oft-quoted 1976 Regents Lecture at UC Berkeley, “Why I Write,” a title borrowed from George Orwell, Joan Didion famously said, “I write entirely to find out what I’m thinking, what I’m looking at, what I see and what it means. What I want and what I fear.”

July 5 marks two years of writing nearly 200 twice weekly personal essays for my paid Substack about the stickier sides of running a small business, and Didion’s words ring true: I often start with the seeds of an idea—a prompt or small story from my life—but I don’t know how I truly feel about the topic or what I have learned until I start writing, especially as the draft simmers for a few days (ideally weeks) before going live.

🧰 With that, here are a few favorite tools to support and enhance your writing—and more importantly, your thinking!—not replace it:

• 🗣️ Claude allows you to upload work samples and create various “voice” profiles called Writing Styles (here’s their how-to guide, and the video announcement). So, for example, if you upload twenty past newsletters (or podcast show notes), it could better help you draft parts of the twenty-first in your voice and style.

• 🛠️

  Jeremy Caplan
  ’s
  Wonder Tools
  newsletter is fantastic; read his Claude 4 overview and, as noted above, his incredibly thorough prompt, “Help me edit.”

• 📘 Check out my Author Toolkit for Loom walkthroughs of how I organize ideas, content, and writing projects with Notion.

• 🎧 Listen to the Behind-the-Book podcast playlist on Spotify

• 👀 Follow along as one of my friends

  Tim Grahl
  tackles his next novel (based on the Story Grid framework) by subscribing to
  Inside the Writing Process
  , watch his video on How to write better with ChatGPT and Kindle, and have fun down the rabbit hole of listening to nearly a decade of Story Grid podcast episodes!

• ✍️ New Rules Studio: A monthly membership community (that I’m in) with twelve optional Zooms a month. You write for fifteen minutes around a prompt, then hear a few people read aloud (always optional), then give and receive supportive feedback based on the Gateless Method.

• 💻 OmmWriter is a desktop app that helps me get in a writing mood: you can choose from seven calming music or white noise tracks, and seven (!) different keyboard clacking sounds that harken back to typewriter days.

• Delphi allows you to create an AI “agent” that others can interact with by uploading a tranche of your own materials (and syncing RSS feeds) to aid business-related tasks like drafting newsletters and searching your own work for snippets and recurring themes. Give the JB bot a whirl, trained on over seven million words from Pivot, Free Time, and Rolling in Doh.

• 🔎 I use Grammarly for copy-editing and catching spelling errors or missing words when I’m ready to schedule a newsletter or essay; just beware that sometimes it overcorrects.

  Sarah Fay
  says, “Be warned that Grammarly will flatten your writing and homogenize your voice. (You know you’ve found your authentic voice if Grammarly hates you.)”

• 🧰 Check out the full Free Time Toolkit in Notion if you haven’t already!

💬 How have you been leveraging AI to help with different writing stages?

Any specific prompts fellow Free Timers might find helpful? Comments are open, so please let us know! 👇

🎙 Related Episodes

069: Epic Evergreen Email Sequences with Allan Dib

070: Rough Drafts vs. The Writers Room

105: “Don’t write the wrong book!” with David Moldawer (Part Two)

225: How to Write a Must-Read Nonfiction Book with AJ Harper

That’s all for now—thank you, as always, for being here!

❤️ With Gratitude,