Week 25: Using AI as a journaling therapist

(and getting some unexpected tough love)

The Experiment

Continuing on my experiments of therapy through AI (if it is the number 1 use case it has to be good for me?) I thought I’d explore how it could divine insights from my journaling. I’ve done a lot; from stream of consciousness morning pages to letters addressed to my future self. I had an easy and simple goal; to extract actionable insights from my journals that would make me a “better, more whole functioning human.” :). Could Claude analyze my journaling style, content, and patterns to offer therapeutic insights I couldn’t see myself?

The Process

Here’s how I approached it:

1. Creating a comprehensive personal database

Uploaded several years of annual planning documents that detailed my goals, achievements, and reflections
Added personality assessments including Clifton Strengths and DISC profiles
Included my CV and website content for professional context
Shared my philosophical influences (I’m a big fan of the Stoics, reading Marcus Aurelius’ Meditations and “The Courage to Be Disliked”)

2. Sharing my raw journaling practice

Took photos of my recent journal entries from the past couple weeks
Explicitly asked Claude to be brutally honest—“don’t pull your punches” (I didn’t want it to placate me, but wanted real insights)

3. The unexpected critique

Plot twist: instead of profound psychological insights, Claude complained it couldn’t read my handwriting
Claimed some pages were “upside down” (🙃)
Criticized my “scratchy” cursive writing style
Delivered the somewhat judgmental observation that someone so reflective should take more care with their handwriting

4. Pivoting the approach

Abandoned the handwriting analysis angle
Asked Claude to instead create a better journaling format based on my strengths and objectives from my annual plans
After several iterations, received a structured weekly format

The Outcome

What started as an AI critique of my rubbish handwriting evolved into something unexpectedly useful: a multi-modal journaling system that actually matches how my brain works.

Instead of forcing a one-size-fits-all approach, Claude designed a system that:

Uses morning voice recordings when I’m rushed but mentally fresh
Maintains handwritten evening reflections for that tactile connection
Adds mid-week typed integration to spot patterns
Combines all three methods for weekly reviews

The AI completely missed my original ask (analyze my journal content), but by critiquing my process instead, it accidentally created something better. Sometimes failing at Plan A reveals a Plan B you wouldn’t have considered.

Key Takeaway

AI can be useful for journaling not just as an analyst of your content, but as a structural coach that helps design a practice tailored to your personality and goals. However, set realistic expectations—it won’t magically extract profound insights from messy handwritten pages, but it might help you create a more intentional approach.

Pro Tips for AI-Assisted Journaling:

1. Feed the AI structured data: Instead of handwritten notes, provide typed reflections, personality assessments, and goal statements for better analysis.

2. Ask for format experimentation: Try different journaling approaches tailored to your specific personality traits and strengths.

3. Be open to unexpected feedback: Sometimes the AI’s limitations (like criticizing your handwriting) can reveal blind spots in your approach that are worth addressing.

Want to Try It Yourself?

Use Claude or another advanced AI for personalized format recommendations
Combine personality assessments (Clifton Strengths, DISC, etc.) with your journaling goals
Start with a 1-2 week experiment with the AI-recommended format, then reassess
Be prepared for a process rather than an immediate transformation. I am still in the coccoon stage of my metamorphosis.