Using AI Memory to Discover Who I Really Am

A personal experiment in self-discovery with the help of artificial intelligence

In May 2025, I was writing a piece on AI therapists and realized that ChatGPT can do a lot more than just take on the role of a therapist. The key feature I was exploring was ChatGPT’s memory functionality. It remembers much of what I’ve discussed with it.

There are two distinct features: “Saved memories,” which the user can define, and “Reference chat history,” where ChatGPT stores many previous conversations. Here’s an explanation from OpenAI on how these functionalities work:

When “Reference chat history” is turned on, ChatGPT will reference your past conversations to recall useful information you’ve shared. It uses this to learn about your interests and preferences, helping make future chats more personalized and relevant. Like custom instructions, when this setting is on, relevant information from your past conversations may be added to new ones. Unlike saved memories, which are kept until you delete them, details from past chats can change over time as ChatGPT updates what’s more helpful to remember. Because ChatGPT doesn’t retain every detail from past chats, use saved memories for anything you want it to always remember.

— ChatGPT Memory FAQ

I asked ChatGPT: “What are some creative ways people use ‘Reference chat history’ in ChatGPT?”

It explained that ChatGPT can act as a personal assistant, capable of working in your style to draft messages, outline blog posts, write code, and more.

But I wanted to go deeper. I wanted to find creative ways to use ChatGPT’s memory for answering personal questions. While reviewing my notes and annual reviews in Roam Research, I noticed I had struggled a lot with identifying my core values.

Why core values?

I knew that living in alignment with my core values would be the most meaningful path forward. During my annual review in December 2023, I set the goal of defining those values in the year ahead. But as 2024 passed, I never followed through.

In my annual review of 2024, I promised myself that in 2025, I would use systems and frameworks to finally uncover my core values.

I had collected these five questions to work from:

1. What are the most meaningful moments in your life?

2. What are the moments where you felt least satisfied?

3. What stories inspire you?

4. What makes you angry?

5. What is your ideal environment?

These questions gave me a path to discover what I truly value. But condensing the answers into clear values was difficult. There was a lot of material to reflect on, but the process of distilling it into something meaningful was tricky and slow.

I started to wonder what would happen if ChatGPT could help me with this assignment. I had shared thousands of lines of text with it over the past two years, so it knew me fairly well.

I asked, “Based on the information you’ve gathered about me, Joakim, what would you say are my five core values?”

The answers it gave were surprisingly accurate. They aligned closely with the five reflection questions I had been working with earlier.

Joakim’s core values, according to ChatGPT

1. Mastery & Excellence

You are driven to be the best—in body, mind, craft, and career. This shows in your pursuit of peak fitness, deep work habits, and world-class performance in VC and writing.

2. Authenticity

You value truth-telling, transparency, and realness, both in how you write and how you relate to others (e.g. in coaching founders, or connecting with your partner and kids).

3. Curiosity & Growth

You’re always learning—languages, tools, musical expression, and human psychology. You gravitate toward what’s new, meaningful, and self-improving.

4. Discipline & Structure

Systems, routines, and deep focus are core to how you thrive. You build environments (mental and physical) that support momentum and clarity.

5. Love & Presence

Whether it’s with your sons, your partner, or the founders you back, you want to be present, intimate, and emotionally available. You work hard to align time with what matters most.

Final words

Here's a few other prompts I've been playing with:

"With all the things I've shared with you, can you create a mission statement for my life?"

"With all the things I've shared with you, can you name five obstacles that prevent me from being happy?"

"With all the things I've shared with you, can you create a list of questions that I could ask every day, so that I know if I'm living the life according to my core values?"