These days, reading often looks like performance.
A stack of annotated hardcovers. A screenshot from Goodreads. A “just finished this” post on TikTok, tagged #amreading and lit by soft afternoon light.
We share what we read to signal who we are. But finishing a book, even a good one, doesn’t mean it changed us.
Some of the most powerful books I’ve read didn’t shape me because I completed them. They shaped me because I kept working with them.
I asked follow-up questions; I challenged their ideas; I used them like mirrors and measuring sticks, and over time, they became part of how I make decisions, notice patterns, and even talk to myself.
Lately, I’ve found myself reaching for a new kind of support in that process: AI.
Not to summarize faster. Not to extract more quotes. But to stay in conversation with the author. To keep the dialogue going.
What follows isn’t a how-to. It’s a reflection on what’s been working for me.
Here are ten ways I’ve been using AI to rethink what it means to engage with a book, and to turn passive reading into something personal, alive, and usable.
1. Build a Custom Podcast From Author Interviews
Sometimes, the real story isn’t in the book. It’s in the interviews.
Authors talk differently when they’re speaking off the cuff. The language is looser. The convictions come through. The ideas evolve in real time.
I’ll collect podcast appearances, keynotes, or book tour interviews and load them into NotebookLM. The result is a searchable, synthesized “author voice” that often reveals context I’d missed. Side notes that didn’t make the final manuscript. Or tensions that the book smoothed over.
What sounds polished on the page often feels more alive in conversation. That contrast deepens my understanding and helps me read between the lines.
2. Turn Downloadable Exercises Into Dynamic Coaching
Many nonfiction books include downloadable PDFs, like workbooks, bonus prompts, and companion guides. I used to ignore them, assuming they wouldn’t offer anything new.
Now, I treat them like personal coaching sessions.
I’ll upload the file and ask ChatGPT to act as the author. Not just to repeat the instructions, but to walk me through each exercise as if we were conversing. ChatGPT might ask a follow-up, challenge a vague answer, or suggest sharper language.
It makes the material feel less like homework and more like a dialogue. In fact, I find I go deeper, not because I’m trying harder, but because the format pulls more out of me.
3. Run a Pre-Mortem on the Book’s Advice
Before I apply a new idea from a book, I’ll ask a counterintuitive question:
What if this completely fails?
It’s a habit I borrowed from Annie Duke’s Thinking in Bets, and it’s one of the fastest ways to move from theory to reality. I’ll describe the advice, add a bit of personal context, and ask AI to walk me through what likely went wrong.
Sometimes the failure is obvious: I didn’t have the time. Or the energy. Or the actual desire. But other times, the pre-mortem surfaces something more subtle, like a hidden assumption the author made that doesn’t fit how I live or work.
It’s not about poking holes. It’s about pressure-testing the idea before it costs you time, energy, or motivation.
4. Simulate a Debate Between Two Authors
Books don’t exist in a vacuum. But they’re often read like they do.
That’s why I sometimes ask AI to simulate a conversation between authors I admire, especially when their ideas seem to pull in opposite directions.
What would Oliver Burkeman say in response to James Clear’s habit frameworks? How might Cal Newport’s deep work principles clash with Annie Duke’s probabilistic decision-making?
It doesn’t have to be perfectly accurate. The friction alone is valuable. But the truth is, ideas become clearer when they’re tested, not just admired.
These small, imagined confrontations don’t just help me understand the ideas better. They help me understand what I’m drawn to and what I’m unconsciously filtering out.
It’s a way of practicing taste, not just comprehension.
5. Use AI to Map the Book’s Idea Lineage
Every book I read is part of something larger, even when it doesn’t say so.
I’ll often ask: “Who influenced this author?” or “Who’s been influenced by them since?” The LLM might surface older thinkers, academic fields, or parallel ideas in unrelated domains.
It’s like turning a single tree into a forest. Instead of seeing the book as a breakthrough, I start to see it as a node in an ongoing conversation.
That shift makes me less precious about any one insight, and more interested in how ideas evolve.
Before We Go Deeper
Around this point, I usually start to notice a shift in how I relate to books.
They stop feeling like finished products and start feeling like open conversations.
That’s what the next few techniques help reinforce. They’re about staying connected with the ideas and with yourself.
Before we move on, here’s a quick question I’ve started asking myself:
What’s one book I’ve finished recently that I haven’t truly learned from yet?
It’s almost always a book I liked, one I underlined and recommended. But for some reason, I never turned it into action.
That’s where the next few techniques often come in.
6. Turn Book Highlights Into Self-Reflection Prompts
Most of my book highlights live in my Second Brain. They feel valuable in the moment, like little trophies of insight. But a few days later, they might as well be someone else’s notes.
So now, I feed them into an LLM and ask it to turn them into self-reflection prompts that actually confront me. Not “What did the author mean?” but:
What does this demand from me?
I remember one in particular: a quote from Essentialism, something about the cost of saying yes without clarity. Claude turned it into a single question:
What are you giving up every time you say yes out of guilt?
I sat there longer than I expected. That question reshaped how I handled my calendar the rest of the month.
A quote about values became a decision filter. A highlight changed a behavior.
In time, I stopped collecting ideas like souvenirs and started using them like tools.
7. Test the Book’s Ideas Against Your Own Life Story
When I’m unsure how a book fits my situation, I do something simple: I give it my story.
I’ll paste in a few short journal entries, work reflections, or decisions I’ve made recently. Then I’ll ask, “What would this author say about how I handled this?”
It’s not always accurate. But it’s almost always illuminating.
Sometimes I see a gap between what I believe and how I behave. Other times, I realize I’ve already been applying the idea, but never gave it language.
Either way, the book becomes more than theory. It becomes a lens.
8. Ask the Book Questions It Didn’t Answer
No book can cover everything. Still, some of the most valuable questions are the ones left out.
That’s why I’ll sometimes ask: “What important questions did this book ignore?” or “What would the author say about [insert my context]?”
Even when the answer isn’t perfect, the act of asking sharpens my attention. It forces me to think about edge cases. To recognize what the author assumed. To notice what’s absent.
And that absence is often where the most personal insights emerge, because what a book leaves unsaid often reveals who it thinks it’s for.
AI helps me surface those assumptions, and in doing so, reclaim the space to ask: “Where do I belong in this story?”
9. Create a “Red Team” Critique of the Big Idea
It’s easy to fall in love with a book’s premise, especially when it speaks to a frustration you already feel.
That’s why I’ve started running a quick “red team” exercise with the help of AI. I’ll prompt it to argue against the core idea of the book:
What are the strongest critiques of this approach?
At first, this felt almost disloyal, like I was trying to tear down something I admired. But over time, it’s become a way to think more honestly. I’m not looking to be convinced out of the idea. Rather, I’m looking to see where it bends or breaks.
I remember doing this with The War of Art, a book I’ve recommended more times than I can count. ChatGPT surfaced something I hadn’t considered: that romanticizing resistance can sometimes mask burnout. That framing helped me realize I wasn’t blocked. I was exhausted. What I needed wasn’t more discipline. It was rest.
Sometimes I come away even more committed. Other times, I leave with questions I didn’t know I needed to ask.
Either way, it helps me move past admiration and into discernment.
10. Codify the Book Into a System You Can Live With
Reading a book is easy. Remembering it is harder. Living it is hardest of all.
That’s why, when a book resonates, I try to ask:
How can I build this into my week?
With AI’s help, I’ll translate the insight into a system: a Sunday night checklist, a Notion dashboard, a recurring journal prompt. It doesn’t have to be complex. It just has to be concrete.
I remember the first time I did this, and how oddly calming it felt, like I’d stopped hoping I’d remember the idea later and started designing a way to keep it close. That one shift turned a book from something I’d read into something I could rely on.
What surprised me most wasn’t the output. It was the quiet sense of alignment that came from knowing I was no longer just collecting good ideas. I was living with them.
Ideas don’t stick because you remember them. They stick because you revisit them.
This is how I make sure the best ones do.
Learning Is a Dialogue. Make It Personal
I don’t remember most of the books I’ve read. But I remember the ones I stayed in conversation with.
The ones that asked something of me. That challenged me to apply, reflect, test, and tweak. That stayed with me, not because I finished them, but because I kept returning.
That’s what AI helps me do. It doesn’t replace thinking. It supports it. It gives me more ways to engage, to adapt, to push back, and to integrate.
And in a culture that rewards speed, distraction, and surface-level takeaways, staying with a book—really staying—feels quietly radical.
It’s not about reading more. It’s about returning to the ideas worth living with.
So, next time you finish a book, resist the urge to close the tab and move on.
Instead, ask one more question. Revisit one old highlight. Test one idea against your own story.
Remember, reading isn’t the final step.
It’s the invitation.
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