My Journal Was Falling Apart. I Taught an AI to Read It.
On September 22, 1988, when I was just three weeks into my freshman year of high school, I pulled out a red spiral-bound notebook I’d picked up for 99¢. I wrote:
Well, this time I am going to seriously try and keep a journal. Writing in it every day. I give myself three days. Perhaps if I set aside ten minutes, I will manage.
While I haven’t written every day, that day marked the beginning of a habit that I’ve maintained regularly for the past 37 years.
My first journal
I started writing because I wanted to be a writer. Pages and pages are filled with notes I took from Writer’s Digest while sitting in the library. I kept writing because it’s the most effective technique I have for understanding my own thinking. I feel like if I stop writing, I won’t know what’s going on inside my own head.
You know what I rarely do? Reread what I have written. I’ve carried these journals around as I moved from one coast to the other, but for the most part they just sit on a bookshelf, untouched. Only three times have I gone back and done any serious reading of what I wrote in my past.
- When my oldest son was about to enter high school, I thought it would be a good idea to reread my high-school journal to remind myself what it was like to be that age. It turns out high-school-me was obsessed with girls in ways I find amusing and embarrassing now. I felt things with an intensity that I just don’t recognize any more.
- When I attended my 25th college reunion, I brought my college-era journals with me and reread them. I was shocked at how many things I described in my freshman year that I have no memory of at all. It was like reading somebody else’s diary! I wrote my crush a fairy tale for her birthday? Really? I guess that’s on-brand for me but I don’t remember it. And while I remember college as being some of the happiest years of my life, the person who was writing some of those entries in 1993 was clearly struggling at times with loneliness and depression.
- When researching this newsletter I reread my journal from the year I got engaged — it turns out my journaling habit isn’t foolproof, and I left no record about how my thinking changed from “only old people get married” to “let’s get hitched.” Oh well.
The way my memory fades really bothers me. I feel adrift, disconnected from my own past. Entire years disappear. Unaided, I can barely tell you what I did between 2002 and 2006, for instance. While I started keeping a journal as a way to understand my own brain, I’ve come to value my journaling habit as a memory aid. For the past seven years, I’ve been keeping my journal electronically, using the app Day One. My favorite thing about that app is it has a “on this day” feature, and now I spend the first 5-10 minutes of my day reading the thoughts I’d recorded in previous years. It’s sacred time. The periodic reconnection helps the past seven years feel fresh and vivid in ways that the prior years do not. As I get older and the past gets longer, this benefit of keeping a journal has become more important.
Day One is keeping me connected to my recent past. What about the deep past recorded in those journals on my bookshelf? How can I make it a regular part of my day to revisit some of the memories in there?
Like everything these days, this is a story about AI.
One thought I had, when I first heard about multi-modal AI models that can understand what is in pictures, was: “Maybe an AI will be able to recognize my handwriting! I could use it to digitize my old journals.” But I did nothing with that thought for a long time. What changed? Duolingo is famously (infamously?) pushing the company to become “AI-first,” and as part of that push I’ve been using AI-assisted programming tools a lot more in my day job. That’s when I learned that these tools are easy to use, powerful, and inexpensive enough for hobby programming. Most importantly, they dramatically lower the barrier for starting new projects. I was confident that if I worked on a notebook scanning app, I wouldn’t be in new-project quicksand, where it feels like you’re learning tools forever before anything works. I was confident I could get the satisfaction of seeing something work end-to-end pretty quickly. That was the push I needed to start this project.
I’m calling what I’m building “Notebook Index”, and it is my attempt to use AI to bring handwritten pages—and the personal history inside them—into a format that’s searchable, durable, and easier to stay connected to. Sunday night, I hit my first big milestone: I now have an AI-generated transcript of the 188 handwritten pages of my first journal, neatly broken down into dated entries. The transcript isn’t perfect—people’s names, in particular, seem to trip it up—but my handwriting’s terrible, so I’ll allow it!
I’ve mentioned that I write to process my own thoughts and emotions, and I’m feeling a lot of things right now:
- It feels awesome to have this digitization. The physical notebook is in sad shape. The pages are yellowing, threatening to fall out, and the notebook is barely holding together. The spiral binding is wrapped in masking tape. I’m feeling so much better with a digital copy that I can back up.
- My digitized notebook feels much more accessible. It’s much easier to go back and read individual entries. I can easily search through the information.
- I’m excited about doing even more! I’m ready to scan all of my journals and write my own “on this day” functionality so I can reconnect with past-me.
Unexpectedly for me, working with AI on this tool has made it feel different from my prior projects. Intellectually, I know my AI tools are just tools… but it still felt like I had an eager assistant willing to work with me on any problem. It was never distracted and never tired. I caught myself trying to match my “assistant’s” energy level and focus. James Clear writes about how, if you want to change a habit, you should join a group where the desired behavior is the normal behavior. It feels like I’ve joined a group where “focus”, “persistence,” and “speed” are the norms.
I love that the AI era dramatically lowers the cost of creating bespoke software like Notebook Index. I don’t know if I’ll ever make this software public, but even if I’m the only user, it is worth it. Writing longhand on paper is fantastic. Staying away from the distraction of screens helps focus. Studies also show that you remember more when you write things by hand. Easy digitization and indexing gives the advantage of searching / archival / backup to the paper world.
As I said, I don’t know if this is a product. But I do know it’s been meaningful to me. And if this resonates with you—if you have shelves of old notebooks too—I’d love to hear from you!