Hey Reader,

Thanks so much for the responses to last week's newsletter How I Finished The Count of Monte Cristo (Without Losing My Mind)!

Some of you asked how to go about picking a book that lends itself to using AI as a companion.

First of all, picking a book to read with AI isn’t about finding the hardest thing you can survive. Instead, choose a book that sparks curiosity.

Perhaps you wonder what all the fuss is about. For me, reading The Count of Monte Cristo was a little about Fear of Missing Out, but mostly I wondered why a story written 180 years ago still captivates readers of all ages.

After having used AI to help me talk through something like 40 books in the past couple of years, I've been thinking about why The Count of Monte Cristo was so much fun.

Here's a super-quick rundown of what I've learned.

📚 What Makes a Good AI Reading Book?

STORY STRUCTURE

✓ Familiar Contexts

• Settings rooted in real history (Victorian London, Ancient Rome)
• Known mythology or recognizable worlds
• Easier to fact-check, easier to enjoy

✓ Clear Plot Lines

• Challenging but navigable pacing
• More Pride & Prejudice, less Ulysses
• Long or dense is fine—pure chaos isn't.

CONTENT DEPTH

✓ Rich Character Relationships

• Emotional layers
• Complex motivations
• Character growth arcs

✓ Historical or Social Commentary

• Political intrigue
• Social dynamics
• Cultural contexts

✓ Multiple Plot Threads

• Interweaving storylines
• Hidden connections
• Satisfying payoffs

BONUS POINTS

✓ Public Domain Availability

• Well-documented analyses (even if you're not interested in the literary lingo or analyses.
• AI models know these titles much better.

🚩 Red Flags: When AI Might Struggle

😵‍💫 Purely Abstract Works

• Pure theoretical texts
• Dense philosophy without story
• AI will bluff harder than a political meme generated straight from the Kremlin.

🧫 Experimental Formats

• Fragmented narratives
• Stream of consciousness
• If you're lost, it might be that AI is lost, too.

🫨 Very Recent or Niche

• New indie releases
• Obscure publications
• Limited AI training exposure

Just to show you how silly AI can be, I asked ChatGPT to add anything I might be missing. Here's what it came up with.

I've found this to be completely untrue. Even when I have begged for a spoiler to help me shortcut through a brutally dense section of a book—I've been unsuccessful at getting ChatGPT to spill the beans. In fact, it lied to me repeatedly, so as to keep me guessing. It's funny now. But it wasn't then.

TL;DR

Is it a classic you've always wanted to read?
Does it have what appears to be a clear narrative structure?
Are you curious about its deeper themes?
This book could be perfect for AI-supported reading!

📖 Tracy's Stretch Reads (My Personal Queue)

• Crime and Punishment - I break out in sweats every time I try to spell Fyodor Dostoevsky.
• Les Misérables - Been intimidated by the length, but fascinated by the French Revolution setting
• The Three Musketeers - Because Alexandre Dumas played me like a fiddle while I was reading The Count of Monte Cristo.

🤖 More AI-Friendly Classics (Selected by ChatGPT)

Except for The Count, I haven't yet put AI through its paces with these books. So don't be afraid to borrow one or two of these titles. Read 3 or 4 chapters and see how it goes. If you're not into the first book you select, move onto the next one.

• The Count of Monte Cristo – Revenge, politics, emotional depth
• Pride and Prejudice – Character motivations, society and snark
• Jane Eyre – Gothic twists, endurance, emotional nuance
• Frankenstein – Ethics, loneliness, ambition
• The Three Musketeers – Loyalty, betrayal, swashbuckling fun
• The Scarlet Pimpernel – Disguises, heroism, hidden identities
• Treasure Island – Lighter adventure but still layered
• Little Women – Sibling dynamics, everyday emotional stakes

🚀 Ready to Start?

1. Pick your book (use our checklist!).
2. Open your AI chat. Use voice or text to ask something like, "I'm reading [Book]. Can you be my reading companion?"
3. Instruct the bot how you want it to respond.
   • Perhaps you tell it to explain a topic like you're a high school student. I need world history and geopolitics explained to me like I'm 12.
   • What's the tone you want when you ask a question? I prefer a hefty dose of snark and humor.

Here's the thing about AI that a lot of people miss. Ultimately, you're in charge of the responses you get—and what you believe about them. Sorta like Facebook and the platform formerly known as Twitter. Only smarter.

TL;DR

Choose something you're already curious about—even if it feels a little intimidating. Let AI be your reading buddy, not your shortcut. You're not racing anyone. You're building a deeper reading life—with a slightly ridiculous, surprisingly helpful sidekick at your elbow.

📧 What's your "someday" classic? Reply to this email and let me know what book you've been wanting to tackle. I'd love to hear your pick!

Thanks so much for reading!

— Tracy

P. S. I don’t sell much. But I do share a lot. If something I’ve written made your week better, here’s a low-key way to say thanks.

​

If you're enjoying Unhustled, you might also like:

Presently Reading Book Club hosted by Maneetpaul Singh Read a new nonfiction book with me and 2,000+ others every month. Subscribe​

As an Amazon Associate, I earn from qualifying purchases made through the links in this newsletter. This doesn't affect your purchase price, but it helps support my work. Thank you!