Cheshire is my personal AI-assisted journaling system that helps me maintain a regular journaling practice. Named after the Cheshire Cat from Alice in Wonderland, this system helps me track my activities, reflections, and progress over time.

Cheshire is inspired by and based on Dan Katt’s Kitty AI. If you’re interested in building something like it you should watch his video about Kitty and check out his example code.

Cheshire is written (mostly) in typescript, and I plan to publish a basic version similar to Dan’s example. I’ll link to that here when it’s published.

How It Works

Cheshire follows a structured daily workflow:

  1. Morning Check-in: Cheshire asks me a set of morning questions to help focus my day
  2. Daily Suggestions: Based on my responses, it generates personalized suggestions
  3. To-Do List: It helps me organize my tasks for the day
  4. Evening Reflection: A second set of questions prompts me to reflect on my day
  5. Journal Entry: Using my morning and evening responses, plus context from previous days, Cheshire generates a daily journal entry

I typically journal on weekdays, occasionally missing weekend entries when I’m away from my computer.

Additional features include:

  • Weeknotes: Weekly summaries compiled from the week’s Q&A sessions
  • Jekyll Integration: Automatically formats and publishes entries to this website

I plan on adding:

  • Images in Journal Entries: I’m thinking I’ll add tags or mark certain photos as favorites, and have Cheshire look for them each day, analyze the images, and add them to journal entries as appropriate.
  • “Agent” Functionality: Currently Cheshire is a collection of scripts that I run manually. I plan to build it into a long-running “AI Agent” application that lives in the terminal and can be interacted with and perform tasks independently throughout the day.
  • đź‘‹Other Stuffđź‘‹

Purpose

My primary goals in building Cheshire are to:

  • Maintain a consistent journaling practice
  • Track my activities, thoughts, and accomplishments (or failures)
  • Identify patterns and insights over time
  • Provide a space for regular reflection
  • Support development of new habits and routines

And as a learning + exploratory exercise to:

  • Gain experience with LLMs and the current state of AI technologies
  • Build with APIs from OpenAI, Anthropic, and local services like Ollama

I’m hoping that journaling and tracking my activities will help my work towards sustainable independence.

Here are a couple posts where I share my experience setting up and first day using Cheshire:

Journal Archives

I don’t expect or intend for these journal entries to be of interest to anyone, but if you’d like to take a look:

View Journal Entries →

Note: While the journal entries are generated from my answers to questions about daily life, they are generated by AI. Any page that includes AI generated content includes <meta name="robots" content="noindex, nofollow"> and should not be indexed.