How I Turned 4,000 Readwise Highlights into a Daily Writing System

I’ve always enjoyed reading. Whether it was to learn for work, enjoy fiction, or gain ideas outside my areas of expertise. In fact, it is one of the ways I learn best. Until 2015 I really didn’t keep track of how much I read. During the holidays that year I started using Goodreads.

While Goodreads was terrific at helping me remember which books I read, it didn’t help me find all of the notes, ideas, and highlights I had collected. It was just a checklist of what I wanted to read and what I had read. I wanted something to turn my enjoyment of reading and self-study into a network effect—generating more value and connections as I read, highlighted, and reflected as part of my daily routine.

I’ve tried several routines and tools. The current routine uses a tool called Readwise.

Limitations Before Readwise

For many years, I had been highlighting in apps like Kindle or O’Reilly library. One issue was that I still read physical books and each digital library was a walled garden. My highlights were all separated into silos. The other issue was that Goodreads was disconnected from my note taking app. That meant I wasn’t always on top of moving the highlights and notes into a place I could easily find them.

My Daily Routine

One: A daily review that resurfaces highlights and topics I’m thinking about.

Two: A read later tool where I can collect PDFs, websites, and email newsletters and prioritize reading them.

Three: Adding more highlights while I read from physical books, online books, websites, and other sources.

Four: Using a chatbot to look up highlights and tagged personal notes from my second brain to use as inspiration for my writing. ¹

Synthesizing

Readwise allows me to sync with all the major online libraries I use, scan sections from physical books, and has a browser plugin. This means all of my highlights with notes are immediately in the Readwise database.

However, Readwise goes beyond that. It also allows me to integrate with my note taking app, Google Drive, and other major technology services. This means my notes are autosynced wherever I need them as I add them. No more copying and sharing. They just appear where I need them.

When it comes to integrations with AI, they have their own chatbot built in. However, they also have a CLI (Command Line Interface) that Claude Code or any other agent could use. If you can’t use the CLI, it also supports Model Context Protocol (MCP). This is how AI like Claude Code understand how to use tools from services like this.

By the Numbers

Since 2016, when I had a full year of data for Goodreads, I’ve read or listened to between 45 and 80 books or a little over 20,000 physical pages equivalent. That is a lot of data to tie together and turn into actionable insights and ideas.

Since 2024, I’ve been using Readwise as my read later and highlight tracking app. The amount of reading remains the same, but my highlights are really starting to stack up.

As of August 26, 2026, I’ve reviewed 6 highlights every day for 743 days. I have created 4,324 total highlights from books, articles, and websites. Now that I’ve done the hard work of curating the best of what I read into key insights, I’ve started using their chat feature to prepare highlights and notes into presentations and writing.

Outcome

I’m using it daily to generate blog posts, presentations, and strategy documents. My output is speeding up from what used to take weeks to days. I’m starting to have one shareable system curated by AI but human-centric.

Footnotes

1. This doesn’t mean the chatbot writes AI Slop. It organizes my highlights to show me what resonated in the material I’ve consumed and written in private notes about specific topics. Then I do the writing. ↩