I gave my journals to AI... here's what I learned [WRAP 187]

Hey Reader,

I did something weird this past week that hit me way harder than I expected. I took 119 pictures of old journals—one from 15 years ago, another from 10 years back—and fed them all to Claude.

It shot back a detailed analysis of my past self that was more revealing than I'd bargained for. Here’s what happened.

What I Discovered

The biggest thing wasn't what had changed, but what hadn't. The core values that mattered to me 10-15 years ago are still important today. But seeing them laid out like this made me realize how little I celebrate my progress—a classic move the goalpost struggle for ambitious people.

It also also revealed some uncomfortable truths. Fifteen years ago, I was really into minimalism, asking myself: "How little can I live on?" Today, I'm thinking: "Can I make $20,000 a month?"

Life and family changes some of that thinking. Back then, no kids. Now I have four, and kids need bigger houses, cars, and more food (so much more food).

But AI helped me see that being a good steward of resources—something that was important to me back in 2010—has remained a personal value through the years.

Your Turn: How to Analyze Your Own Journals

If you want to start having conversations with your younger self, try this:

Start with one notebook: Take pictures with your phone and upload to AI. Ask it to analyze the journal entries and give you trends and summaries. Don’t settle for the first reply, keep clarifying and asking more questions.

Create separate conversations: Give each notebook its own chat. This prevents overloading and keeps the context clean for better analysis.

Use AI Projects: If you're on a pro plan ($20/month), create a dedicated project for your journal conversations. This maintains better context across multiple notebooks.

Push for brutal honesty: AI is naturally encouraging. You must tell it: "I need you to challenge me and show me where my past statements don't match my current actions."

Keep using it: Don't just analyze and forget. Use your AI-analyzed journals as an ongoing resource for decisions and problems. You now have years of personal wisdom at your fingertips!

The Real Magic

This experiment gave me something I didn't expect: a way to have conversations with past versions of myself that were previously impossible. It helped me appreciate progress I'd overlooked and reconnect with values I'd completely forgotten about.

When you’re obsessed with personal growth, its’s tough to pause to celebrate how far you’ve come. Like me, you’re already chasing the next goal. But you need to hold up a mirror and see both who you were and who you've become.

Your journals are sitting there, full of insights you've forgotten. Maybe it's time to let AI help you rediscover them.

By the way, I'm working on a video about AI journals. It will go live on September 15th, but in the meantime check out the ASMR planning video I made. It's only 3 minutes and all you hear are the sounds of a monthly planning process.

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See you next week,

Matt "Memory Bank" Ragland