• Nov 05, 2025 *

Context: This post is about a project I’ve been working on for while - codename “Charlie”. I presented the slides below at the Recurse Center for a talk called “Conjuring a Conspiracy Kitty”; explaining why Charlie should exist.

After a particularly long stint of regrettable mistakes in my early entire 20s, I started journaling so I can reflect on my thoughts (for once). I bought a little black notebook, titled it “Lessons Learned the Hard Way”, and drew a stick-figure falling off a cliff on the cover. That was back in 2015, I’m still journaling every day a decade later.

Journaling has helped me avoid making poor decisions, apologize when I inevitably do, and to have an honest check-in every night before bed. The goal is to wake up a bit more self-aware.

Although journaling helps me solve many problems, I now have a few others I didn’t anticipate, so I’m trying to code my way through them.

First issue is volume; I’ve got more entries than time or energy needed to reread them. Occasionally I’ll reread the “1 Year Ago” entry that my current journaling app provides, but that’s a single frame; disconnected from all others going forward and back in time. The storyline that captures the who, what, where, is broken and discrete.

I initially tried giving some of my journal entries to ChatGPT to talk about; but that wasn’t a good idea. For one, I REALLY don’t want to be regularly sharing my thoughts with Google, OpenAI, etc. at such a personal level. Yeah Google knows everything, but my journals are the last private digital domain I have sovereignty over.

Even if the privacy issues were somehow addressed, I’ve got too much text to fit inside a single conversation. Besides, I’ve got very specific needs for the kinda data I want to see.

I’m talking Time-Series Aggregation - rolling up days into weeks, weeks into months, months into years, etc. For any given period of time, I want to know the following things:

• What did I spend most of my time & energy thinking about?
• Who was I spending time with? What kind of company did I keep?
• What lead me to take the actions I did?

Other journaling software can sorta do this, but they’re often too wholesome and focused on their chosen frameworks of wellness and self-improvement. I should be able to read about my daddy issues in CSV.

I want to navigate the connections between people, places, ideas, and actions - to click on people’s names and read more about our interactions. I want to click on feelings mentioned and see other dates where I felt the same way. I want summaries so I can experience a whole month in one page. And I want to have all this privately, on my own device, on my own terms.

That’s why...

I’m creating Charlie; a private, local-first journaling tool that automatically constructs a knowledge graph for you to explore. It’ll connect the dots so you can find patterns of thought & behavior to (hopefully) help raise your self-awareness. “Cool” you might say, but “why is it called Charlie?”. Well...

My current journaling app is called Day One, and I’m inspired by Charlie Day of “It’s Always Sunny in Philadelphia” from the Pepe Silvia episode. Long story short; he convinces himself that everything is connected and there’s a major conspiracy with him at the center of it, so he covers the room in red yarn to connect all the dots. I’m not planning on losing my mind, but Charlie will probably suck for a while, connecting random things and making shit up; a fun way to fail for a while. Besides, cats love yarn, and every good piece of software needs a mascot. 😼

Say hi to Charlie everyone; he’ll be a regular here from now on.

#ai #charlie