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The Practice: Using AI as a Mentor for Morning Journaling

A New Yorker-style cartoon of Bigfoot visiting a therapist office in Manhattan

We can read self-help books alone, but there’s nothing to ensure we draw the right conclusions about ourselves from them. We can journal alone, same problem. Our hero narrative can be strong. Our neuroticism can be strong. An objective voice with a huge ability to retain details and spot patterns is powerful.


The Morning Routine

Every day at 6 AM, before my wife and son are up, I go to the gym. Then I sit down with a notebook and write. Stream of consciousness. No prompts, no structure, no screens. Pen on paper until I’ve filled at least a page.

I picked up Julia Cameron’s The Artist’s Way in the late 90s. Morning pages have been part of my routine for most of the years since. She’s specific about what they are:

Three pages of longhand, stream of consciousness writing, done first thing in the morning. There is no wrong way to do Morning Pages.

Just whatever is in your head. Don’t edit. Don’t plan what to say. Just move the pen.

Writing by hand slows your mind to the speed of thought. Stuff that loops in your head all night becomes finite when it’s on paper. You don’t write to produce something. You write to get it out.

The AI comes later.

What Happens After the Pen Goes Down

I photograph the journal pages and drop them into a folder. Claude reads my handwriting, transcribes it, and stores the text in a SQLite database. A folder and a database. That’s the whole backend.

As part of the transcription, goals get automatically extracted and tracked. Long-term aspirations go into one list. Daily tasks go into another. I don’t maintain any of it. The system reads what I wrote and figures it out.

Every week, I sit down with Claude for about 50 minutes and review the entries. It surfaces patterns. Recurring anxieties. Goals that keep showing up. Emotional themes I wouldn’t notice on my own. It tracks what I accomplished, what I deferred, and what I’m avoiding.

The Self-Cleaning System

If you’ve ever used Notion, Apple Notes, Obsidian, or any “second brain” tool, you know how this goes. You set up folders. You make lists within lists. You build a tagging system. It feels great for two weeks.

Then life happens. You stop curating. Notes pile up in the wrong places. After a while you dread opening it.

Nate B Jones made a video about building a second brain that stuck with me. His system is different from mine, but his point landed: self-curated systems usually fail. The best system is the one that maintains itself.

That’s what this does. The goal tracking is automatic and always clean. I found myself naturally writing goals on the right-hand page of my journal. It just happened, but it works. I can mark things done as I write the next morning. If I forget, I tell the AI during the weekly session. Especially useful when it flags something like “you set this goal two weeks ago and never came back to it.”

When a goal keeps getting deferred, it means something. Sometimes the goal doesn’t matter anymore. Sometimes there’s resistance you haven’t faced. The spillover tracker makes avoidance visible. Visible avoidance is harder to ignore.

The Human Does the Feeling, the AI Does the Noticing

The journaling is deliberately unstructured. That’s the point. You’re not filling out a form. You’re dumping the contents of your mind onto paper. Dreams, worries, half-formed plans, nonsense. All of it.

But unstructured data is hard to learn from over time. You could flip back through three weeks of pages and look for patterns, but you probably won’t. My handwriting isn’t even legible enough for that anyway. The whole point is that this is throwaway writing. It’s not good writing. It’s writing that means something only through slow accrual. The AI is what makes that accrual visible.

Because it’s read every entry, it can connect things across weeks that you’d never connect yourself. “You mentioned this anxiety on three separate days” is a different kind of insight than just feeling anxious.

This isn’t AI therapy. It’s AI-assisted self-awareness.

The Stack

The whole thing took an afternoon to set up. And that matters. Ever try Covey’s system, or Getting Things Done, or even a simple spreadsheet to track goals? You end up either lost in the process or fiddling with the tech. This is a notebook and a camera.

What I’ve Learned So Far

The patterns are real, and you genuinely cannot see them yourself. Having goals extracted and tracked automatically changes your relationship with procrastination. It’s no longer something you can quietly ignore.

The weekly review is the most valuable part. It’s like talking to someone who’s read your diary and isn’t afraid to be honest about what they see.

One unexpected bonus: I’ve started remembering my dreams. Writing first thing in the morning, before any screen, before any input from the outside world, you catch things in that half-awake state that would otherwise evaporate. The journal captures them. The AI remembers them. Weeks later, it can tell you what you were dreaming about.

The Practice

I call this project “The Practice” because that’s what it is. Not a product, not a system, not a life hack. A daily practice. The discipline is the handwriting. The AI just makes sure you’re listening to yourself.



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