Revolutionizing Shallow Thinking: How Readwise’s Two New Features Transform How Busy Professionals Process Information

This weekend, Readwise shocked the productivity world with two game-changing features: “Chat with your highlights” and “Other relevant highlights.”

These additions have completely transformed how busy professionals can extract value from their Shallow Thinking system, turning years of accumulated highlights into an interactive knowledge base that works for you.

The timing couldn’t be better.

Just as the challenge of managing information overload reaches new heights, Readwise delivers a solution that makes your captured knowledge truly actionable.

No more passive storage – your highlights can now answer questions, reveal connections, and surface relevant insights exactly when you need them.

In this article, I’ll show you why these features are revolutionary for busy professionals, and how they’ve elevated the Shallow Thinking system from simple information capture to an AI-powered insight engine that amplifies your productivity with minimal effort.

Let’s dive in!

Shallow Thinking: Your First Line of Defense Against Information Overload

Shallow Thinking is your rapid-response system for managing the daily tsunami of information.

It’s the quick capture and retrieval of valuable content, processed almost instantaneously using simple methods like tagging or fast categorization.

Think of it as your first filter against information overload.

Here’s where it gets interesting: Shallow Thinking operates in two distinct worlds – your Inner World and the Outer World.

Your Inner World is all about the content you create: your thoughts, ideas, meeting notes, and any content where you’re the source. It’s your personal knowledge factory, requiring its own specific approach to quick capture and organization.

The Outer World, on the other hand, is where Readwise’s new features truly shine. This is all the external content you encounter daily: articles, books, podcasts, YouTube videos – anything created by others.

While you can enhance this content with your insights and annotations, managing this flood of external information has always been a unique challenge.

“Knowledge is of two kinds. We know a subject ourselves, or we know where we can find information upon it.” — Samuel Johnson

The beauty of Shallow Thinking lies in its speed and simplicity in both worlds.

No complex systems, no deep analysis – just rapid capture and easy retrieval when you need it.

But today, we’re focusing on how Readwise has revolutionized how we handle the Outer World portion of our Shallow Thinking system.

Highlights: Your Building Blocks for Actionable Knowledge

Picture this: You’re reading an article, watching a video, or diving into a book when suddenly – there it is.

That perfect insight. That game-changing idea.

That’s a highlight – your fundamental unit of captured knowledge.

But here’s where it gets interesting: when integrated with Readwise’s spaced repetition system, these highlights transform from passive notes into active elements of your Shallow Thinking system.

The journey to this realization wasn’t straightforward.

As an early adopter of Readwise, I’ve spent years refining how I process information from the Outer World using the ICOR® methodology.

Like many busy professionals, I faced a common frustration: consuming vast amounts of content without extracting lasting value.

Something had to change.

This led me to completely redesign my approach, drawing five crucial conclusions that transformed how I handle information coming from the Outer World:

1. Radically decrease the number of books I read yearly, moving from 52 (yes, I was one of those who believed in these nonsense goals) to just 1-3 books that truly matter.

2. Deeply analyze, study, and reframe these few books within my Deep Thinking system, using my own thoughts and wording.

3. Take concrete action based on the book’s conclusions.

4. Focus on channels that deliver ideas in small, digestible pieces that spark inspiration, like X (formerly Twitter) or Deepstash.

5. Double down on a solid tool stack for managing Outer World content, settling on just three core tools: Readwise, Readwise Reader, and Mymind.

The solution emerged through the Capturing Beast workflow from ICOR®.

Readwise Reader became my gateway for sending everything to a Single Source of Truth, allowing me to quickly tag content with my buckets (a concept we define in the ICOR® methodology).

Mymind handles visual content, while Readwise stores my highlights for spaced repetition.

But here’s where everything changes – taking action on content isn’t just about storing it.

In my experience working with busy professionals for decades, meaningful action on Outer World content breaks down into two essential approaches:

1. Going deeper into complex content (like a book) through careful analysis and integration into your Deep Thinking system.

2. Leveraging spaced repetition to ensure key insights stay fresh and accessible in your mind, ready to be applied when needed.

The first approach deserves its own deep dive in another article.

For now, let’s explore how Readwise’s revolutionary new features have transformed the second approach into something far more powerful than traditional spaced repetition.

Spaced Repetition: Your Secret Weapon for Information Retention

Think about how many brilliant insights you’ve encountered and then completely forgotten. Frustrating, isn’t it?

That’s where spaced repetition comes in – it’s the science-backed technique that helps you remember information by reviewing it at precisely the right intervals.

Instead of the traditional “read once and forget” approach, spaced repetition strategically schedules your reviews at increasing time intervals. Each review occurs at the optimal moment to strengthen your memory, making the information stick with minimal effort.

For years, Readwise has excelled at this.

Five minutes of daily review keeps your highlights fresh and actionable. You decide what resurfaces and what doesn’t, and the system handles the rest.

“We are drowning in information but starved for knowledge.” — John Naisbitt

But here’s the thing – despite the power of spaced repetition, I’ve always felt something was missing.

As a busy professional with an extensive Shallow Thinking system dedicated to the Outer World, I knew there was untapped potential in my highlights.

Sure, I was capturing insights and reviewing them regularly, but was I really extracting their full value?

That nagging feeling persisted until now.

Readwise has just launched two features that don’t just enhance spaced repetition – they completely transform how we interact with our accumulated knowledge.

Let’s start with the game-changer: “Chat with your highlights.”

“Chat with your highlights”: AI-Powered Insight Mining

Imagine having a brilliant research assistant who has read everything you’ve ever highlighted from the Outer World – every article, book, and piece of content you’ve encountered – remembered it perfectly, and can instantly connect dots across years of your captured insights.

That’s exactly what “Chat with your highlights” delivers.

This isn’t just another AI feature – it’s a fundamental transformation of how we interact with our Shallow Thinking system for Outer World content.

For the first time, we can extract insights from our highlights that go beyond our own knowledge or common sense, discovering connections we could have never imagined.

I’ve always built my Outer World Shallow Thinking system around three core principles:

1. Lightning-fast capture of external information.

2. Zero time spent on organizing content from others.

3. Meaningful resurfacing of insights from the Outer World.

The first two principles were solved long ago with tools like Readwise Reader.

But that third principle – making information from the Outer World resurface with genuine meaning and insight – has always been the holy grail.

The Game-Changer: How “Chat with your highlights” Revolutionizes Outer World Knowledge Management

This feature hasn’t just improved my Outer World Shallow Thinking system – it has fundamentally transformed it. Let me show you how.

First, it’s revolutionized how I retrieve value from my captured content.

Instead of passive reviewing, I can now engage in dynamic conversations with my highlights, uncovering new insights and perspectives I never would have connected on my own.

The magic lies in its semantic understanding. When I ask about “budget,” for instance, it automatically explores related concepts like costs, finances, and money across my entire highlight collection. This semantic search brings previously hidden connections to light.

But here’s the real breakthrough: it makes all my captures immediately useful without any organizational overhead.

No more complex tagging systems. No more manual linking. No more time wasted on organization. Just capture and let AI do the heavy lifting.

This has completely eliminated my FOMO (Fear of Missing Out) around content consumption.

I can now capture anything that seems potentially valuable, knowing that AI will help me extract meaning from it later. The retrieval process has become fast, engaging, and genuinely useful.

Most importantly, I’ve finally achieved what I’ve been dreaming of for decades: my own private Google/Perplexity-like search engine, but one that searches exclusively through my curated knowledge.

It doesn’t matter how much content I store – just like these search engines make sense of the internet’s vast content, this Outer World Shallow Thinking system transforms my personal collection of highlights from overwhelming noise into meaningful signal, surfacing relevant insights exactly when I need them.

But here’s where it gets even more interesting – “Chat with your highlights” is just the first part of Readwise’s breakthrough.

The second feature, “Other Relevant Highlights,” takes this transformation to an entirely new level, creating connections I never thought possible.

Let me show you how this powerful duo is changing everything…

“Other Relevant Highlights”: When AI Becomes Your Personal Knowledge Connector

If “Chat with your highlights” transformed how we retrieve information, “Other Relevant Highlights” revolutionizes how we discover connections within our knowledge base.

Here’s how it works: whenever you’re reading a highlight, Readwise automatically surfaces other relevant highlights from your collection.

But this isn’t your typical “you might also like” suggestion – it’s something far more powerful.

Think about the manual linking you do in your Inner World PKM system.

The careful tagging, the meticulous creation of connections, the endless maintenance of backlinks.

Now imagine all of that happening automatically, but with an AI that can see patterns and relationships you might never have considered.

This is what makes “Other Relevant Highlights” truly revolutionary.

“The greatest enemy of knowledge is not ignorance, it is the illusion of knowledge.” — Stephen Hawking

It’s not just matching keywords or tags – it’s understanding context, concepts, and relationships across your entire collection of highlights from the Outer World.

With the vast amount of content we capture daily, it’s humanly impossible to remember and connect everything we’ve stored. But AI excels at exactly this kind of pattern recognition.

I’ve been consistently amazed by the connections this feature surfaces – linking highlights from articles I read years ago with recent captures, connecting ideas across completely different domains, and revealing patterns in my reading that I never consciously recognized.

Why Context Makes All the Difference: Readwise vs. Generic AI Tools

As a computer science engineer who’s both coded and analyzed countless software products, I’m seeing a concerning trend: companies rushing to implement AI just to check a box.

Most of these implementations are superficial – why use a tool’s basic AI when you could just go straight to ChatGPT for more sophisticated responses?

Readwise’s approach stands apart because they’ve implemented AI in a way that ChatGPT simply cannot compete with.

Instead of adding basic AI features that merely replicate ChatGPT’s capabilities, they’ve created an AI system that operates exclusively within your personal knowledge domain – your highlights, your interests, your patterns of thinking.

Here’s why this is technically superior: I’ve created a natural information funnel through my Outer World Shallow Thinking system.

1. From the vast sea of content, I capture what resonates.

2. From those captures, I highlight what truly matters.

3. This creates a highly curated, personally relevant dataset that no general-purpose AI could ever access or understand.

What makes this implementation particularly impressive from a technical standpoint is Readwise’s sophisticated backend architecture.

I’ve always maintained that Readwise’s real power lies in its robust relational database model – a foundation they’ve been meticulously building since the product’s conception.

This isn’t just another PKM tool with AI bolted on; it’s a carefully designed Outer World Shallow Thinking system where every highlight, every tag, every connection is structured for optimal retrieval and relationship mapping.

What’s particularly brilliant is how this technical sophistication translates into a natural, frictionless user experience.

There’s no need to learn special prompts or commands – you simply interact with your highlights the way your common sense dictates, and the AI responds intelligently.

This seamless integration means you can extract maximum value from AI without ever leaving your workflow or context-switching to another tool.

Now, with these AI features, we’re finally seeing the full potential of this architectural decision.

The AI isn’t working with a flat collection of highlights – it’s leveraging a rich, interconnected web of information, where each piece of content maintains its original context, source, and relationships.

This is what makes tools truly shine: when they’re designed with a specific, well-defined purpose from the ground up, rather than trying to be everything to everyone.

It’s particularly effective for tools based on “small bites” of information.

That’s why I’ve always believed in the “idea approach” – tools like Readwise (highlights), Tana (nodes), or Deepstash (ideas) that excel at handling discrete units of knowledge.

These tools are powerful precisely because they’re full of small insights that are easy to consume (perfect for our crazy, fast-paced world) and spark inspiration based on our current knowledge or situation.

This approach has even eliminated one of my biggest pain points: manually connecting my PKM tools to my highlights.

That manual connection was creating more noise than signal in my PKM system, which is why I had previously abandoned it entirely.

Now, with these two Readwise features, I can effortlessly create signal from noise, extracting meaningful insights from my accumulated knowledge with zero manual overhead.

Your Next Steps: Transform Your Outer World Shallow Thinking System Today

Let me share why this is a game-changing moment for busy professionals managing Outer World content.

First, you can finally stop worrying about how to organize your highlights.

Just capture what resonates – Readwise’s AI will handle the heavy lifting of making it useful later. This alone will save you hours of manual organization and tagging.

Second, you’re now free to capture more broadly.

That article that seems tangentially relevant?

That YouTube video that sparked an idea?

Capture them!

The AI will help you surface these insights exactly when you need them, creating connections you might never have seen otherwise.

Here’s how to get started immediately:

1. Begin using “Chat with your highlights” to explore your existing knowledge base. Ask questions about topics you’re working on – you’ll be surprised by the insights hiding in your own highlights.

2. Pay attention to the “Other Relevant Highlights” feature when reviewing any highlight. These connections often reveal patterns in your thinking and learning that can lead to breakthrough insights.

3. Stop manually connecting your PKM tools to your highlights. Let Readwise’s AI handle these connections – it’s more efficient and creates less noise in your PKM system.

The real power here isn’t just in the technology – it’s in how it transforms your relationship with information from the Outer World.

You’re no longer just collecting highlights; you’re building a dynamic, AI-powered knowledge base that grows smarter with every piece of content you capture.

For busy professionals, this means you can finally focus on what matters: consuming valuable content and extracting insights, while letting AI handle the complex task of making it all accessible and actionable when you need it.

This is just the beginning of how AI can enhance your Shallow Thinking system.

And, Readwise has shown us the right way to do it: not by replacing human thought, but by making our existing knowledge more accessible, connected, and actionable.