Week 24: Using AI as a personal therapist

(Surprisingly effective, surprisingly flawed)

The Experiment

I was looking at the top uses of AI in 2025 and I was surprised to see therapy at the top. This isn’t my priority usage. I know that my dear readers (and my wife) think that I am perfect in every way, but I thought I should explore this use case in more detail. With a 10-day break ahead and some time for self-reflection, I decided to test whether AI could help me unpack my thoughts and provide meaningful insights.

I wasn’t looking to address trauma or deep-seated issues—just wanted a lightweight, mobile-friendly process for personal reflection and growth. Something that might surface new perspectives about myself without the hourly rates of traditional therapy.

The Process

Here’s how I approached it:

1. Research and Design

Spent some time discussing options with ChatGPT to understand what approach might work best
Explored CBT (Cognitive Behavioral Therapy) frameworks and journaling techniques
Drew inspiration from Anna Gat’s powerful prompts shared on Twitter
Designed a minimal viable process that would work entirely on my phone

2. Setting Up the System

Created a Google Keep template with thought-provoking prompts
Built a custom GPT trained on my DISC profile for personalized feedback
Established a workflow: Daily prompts → Reflection → AI analysis → Insights collection

3. The Daily Practice

Each day, I’d clone the Keep template and fill in my thoughts
Take screenshots and feed them to my custom GPT
Collect the most valuable insights into a Google Doc to track themes and patterns
Occasionally used ChatGPT directly with its memory of our conversations for broader context

4. The Power of Prompts

Some questions hit surprisingly deep: “If I died tomorrow, what would you say I stood for—based on our conversations?”
Others revealed blind spots: “What do I actually want—but still don’t feel safe admitting?”
The AI even quoted Werner Herzog back at me in discussing my search for “ecstatic truth”

The Outcome

This experiment yielded mixed but intriguing results:

Custom GPT Limitations: My purpose-built GPT seemed to lean too heavily on my DISC profile, returning to themes of “people pleasing” :) regardless of context

Memory Advantage: Standard ChatGPT with its memory of our conversations provided more nuanced, contextualized insights than my custom solution

Surprising Depth: Some of the exchanges led to genuine “chin-stroking” moments worth discussing further

Spouse Bonus: My wife tried similar prompts with positive results, suggesting the approach has broader applications

While not perfect, the process was remarkably accessible and yielded genuine insights with minimal investment. The experience was enough to make me want to continue, albeit with some refinements to the approach.

Key Takeaway

AI therapy won’t replace human therapists, but it offers a surprisingly effective, accessible, and affordable alternative for personal reflection. The key isn’t in building complex systems but in asking the right questions and leveraging the AI’s ability to spot patterns in your thinking.

Pro Tips for Beginners:

1. Start Simple: You don’t need complex setups—begin with thoughtful prompts and standard AI tools

2. Use Memory Features: If you’ve used ChatGPT extensively, enable its memory function for more personalized insights

3. Ask Uncomfortable Questions: The most valuable insights often come from questions you’d rather not answer

4. Iterate Your Approach: Don’t stick with a process that isn’t working—be willing to pivot as I did from the custom GPT to standard chat

5. Personalize Your Process: Everyone has different areas of focus—what works for one person may not work for another

Want to Try It Yourself?

Use powerful prompts like: “If I died tomorrow, what would you say I stood for?” or “What do I actually want—but still don’t feel safe admitting?”
Start with standard ChatGPT or Claude before building custom solutions
Keep a record of insights to track patterns over time
Remember it’s cheaper and more accessible than traditional therapy, though perhaps not as deep