Why your AI keeps forgetting everything


A few days ago, I asked readers, “What’s your biggest frustration with AI?”

Then, I promptly (boom, boom!) decamped to the sunny south east of Ireland for a few days away with the fam.

I came home and found dozens of responses in my inbox.

I’ll answer them here over the next few days.

First up is Benjamin.

He wanted help with this problem:

“The erratic retention of earlier conversations, especially involving extended explorations of pillar posts, site architecture, and market assessments.”

Swap out “pillar posts, site architecture, and market assessments” for whatever you’re working on e.g. blog posts, social media content, articles, stories, etc.

Now you can address AI’s memory problems in several different ways.

First up, in ChatGPT:

  • Navigate to settings
  • Ensure reference saved memories and chat history are turned on.

Next, click Manage memories. Now, review all of the memories inside of ChatGPT and delete ones that are out of date.

ChatGPT also reassures me that the latest model (GPT 5) automatically references past chats.

I’m a skeptic, so I also regularly prompt GPT (or Claude) to summarize our chats, and then I use the outputs for my AI projects.

I start new conversations by pasting previous conclusions and goals. I also include relevant background from past chats in my first message.

In short, I prompt, evaluate, summarize, and reprompt.

I treat each AI chat like working with a consultant who needs fresh context every time.

I explain more about how to do all this inside Prompt Writing Studio. Check that out here.

If you have more questions about using AI, write in and ask.

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