What if an AI could search every book you’ve ever read and find the exact insight you need — condense years of reading on a topic, or compare how different authors approach the same question? I’m experimenting with Claude Code to make this real: teaching an LLM to navigate my entire Kindle highlight collection and become an intellectual sparring partner.

Your reading history contains years of insights, but they’re scattered across dozens of books. When you need to pull together everything you know about a topic, those highlights feel unreachable.
We’re building new cross-library AI workflows for DeepRead that transform this scattered knowledge into structured outputs. Through guided conversations, the AI helps you generate topic memos or mind maps that synthesize insights from across your entire library. The key difference from traditional AI chat: the system has persistent access to your complete reading history, not just what you upload. Every interaction creates something tangible and makes your knowledge system more valuable.
We’re developing these workflows now and looking for early users to test features and share ideas.

Systematic highlighting is hard work—but it unlocks four powerful ways to engage with books through AI.

Each workflow creates a tangible artifact—not just another chat that disappears. This article shows you these workflows: building mind maps, generating meaningful flashcards, challenging the author’s arguments, and capturing insights with visual connections. I’ll explain why comprehensive highlighting—the Composer strategy from my previous article—makes all of this possible. We’re also exploring how to bring these workflows into DeepRead.

Most readers highlight reactively—marking whatever seems important as they read. But effective highlighting starts before you open the book: by choosing your strategy and defining your desired outcome. The difference between collecting treasures and composing arguments determines everything that follows.

Some books function as learning systems rather than mere content delivery vehicles. They do this by using design elements such as quotes at the start of chapters, highlighted questions within the text, or chapter summaries at the end. These elements create a reading architecture that guides you through three phases: preparation, exploration, and synthesis. The real power lies in actively using these elements to transform any book into your personal learning laboratory. This way every book becomes an expedition where you decide what to discover and take home.

The best book discussions aren’t happening in traditional book clubs—they’re scattered across Reddit threads, X debates, and comment sections, but we’re missing them because we don’t know how to connect our reading insights with ongoing conversations. This article explores how to create “book clubs of the future”: time-independent, globally scaled discussions where your specific book insights connect with current debates happening across the internet. You’ll discover existing platforms where these conversations are already taking place, see real examples of authors and readers successfully applying book knowledge to current events, and learn practical steps to start participating today.

The easiest way to move from passive reading to active learning? Start talking. Voice AI conversations are the lowest-friction way to test your knowledge, practice complex ideas, and build confidence – all without judgment or pressure. Here’s why this approach works and how to get started.

You’ve just finished a fascinating book, but within days those brilliant insights start slipping away—scattered, inaccessible, lost. You know you’re losing something valuable, but organizing it feels like too much work. What if securing those fleeting insights could actually be fun? What if a simple conversation could turn your scattered highlights into a structured mind map, sparking new connections and ideas you hadn’t even noticed? Our new conversational AI approach transforms the tedious work of knowledge management into an engaging dialogue that makes your insights stick. This feature is on our roadmap, and we’d love your feedback as we design it.

During my experiment to actively learn from audiobooks, I have started using AI to transform my pile of scribbled notes into a lasting knowledge graph. Now, I have discovered something counterintuitive: the best way to use AI for learning isn’t to let it summarize content for you, but to make it your co-worker in transforming your own imperfect recall into structured knowledge. Instead of asking AI to understand the book, I ask it to help me understand what I’ve understood—and the results are transforming my relationship with audio learning.

A week ago, I started an experiment. Instead of falling into my usual pattern of buying both the audiobook and the ebook version of “Broken Money” by Lyn Alden, I decided to challenge myself: Could I extract maximum knowledge from just the audiobook? Could I build a comprehensive knowledge graph without ever opening the Kindle version?

The stakes feel higher than usual because this isn’t just about saving money or time. It’s about fundamentally changing how I approach learning from audiobooks. And honestly, I’m not sure it’s going to work.

If you’re like most audiobook listeners, this scenario probably sounds familiar: You finish an excellent book, feeling inspired and full of new insights. A week later, someone asks you what the book was about, and you struggle to recall more than a few vague concepts. A month later, you can barely remember the main thesis.

Flashcards combined with the Spaced Repetition System is a solid way to learn and remember the main ideas of what you read. With this approach you break down your book into small, digestible pieces of knowledge and create flashcards to trigger active recall. The Spaced Repetition Method makes sure that you test your memory at strategically timed intervals with shorter intervals for harder to remember content and longer intervals for easier content.

But there’s a challenge: when you break a book into individual pieces, you might lose sight of how everything connects. Depending on the type of book and your learning goals, you may need to preserve not just individual facts, but also the structure of arguments and how different concepts relate to each other. This can be achieved by adding cards that focus specifically on the book’s organization, or by including hints on regular cards that remind you where each piece of information fits in the author’s overall argument.