Feed Me! A Boomer's Journey into AI
- James Massa

- Jun 24
- 3 min read
Feed Me! Feed Me! Your AI wants to be fed as much as you can give it. Unlike the most recent generations, most boomers (as in the full name, “baby boomers”), raised children to adulthood. It turns out this is great preparation for the new age of AI. You are used to hearing in one form or another “Feed Me!”. So, what’s the best diet for your favorite AI?

In general, AI’s consume data. In every interaction you have with your AI it absorbs data about you in dimensions too many to name. This includes what you actually share, how you share it, what time you share it, from where you share it, what patterns emerge in your sharing, and much more. Today’s generations share everything about themselves, including a whole lot of TMI, openly on line to the world to absorb. In contrast, being a boomer, I was raised to not share my social security number with anyone. This is an example of the deep seeded resistances to sharing information with your AI that you may still have. However, “Sharing is caring” for yourself as you interact with your AI.
Some interaction you have is casual information gathering. What is the weather today? Who was the 28th President of the United States? Where exactly is the country of San Marino? You ask a question aloud and get an answer.
Yet, when I am doing deeper work, whether it be planning a vacation or creating a proforma or writing a new book, I find it easiest to interact with my AI by typing. Feeding your AI becomes as easy as dragging and dropping a file onto the AI prompt line or clicking on the plus sign “+” and searching for it on your device. Then several amazing things happen and don’t happen that initially astounded me.
Instantly, and I mean instantly almost no matter how large the file is, the AI has not only “read” but has analyzed your file. It’s not just uploaded it has complete ingested it. It has access to every part. Most importantly, it can interact with you on any aspect of it. Often it even has opinions regarding whatever you have provided.
Surprisingly, the file is not always remembered by the AI if you come and go from your interactions. Some AIs now feature, for a monthly cost, a file library of sorts to which any of the chats you have with the AI can refer. This makes your files more “persistent” for future reference. However, in most instances, files are kept in a temporary memory space. Most importantly to know, any files the AI generates for you are only kept in the temporary memory space. One the interaction is over, they may no longer available to the AI.
Let me Boomer-splane this. The best way to think about the interactions you have with the AI and the files you upload is that it is as if you have met with a consultant in a publicly available meeting room. You first have to bring everything you want to share into the meeting room. Then, when you leave the room, sometimes the materials you have brought to the conversation remain on the table. Other times the materials are cleared out quickly by a cleaning service that keeps the room clean. Oddly, the files (ie. materials) you brought or the AI generated may be gone. However, the notes from your meeting are still up on the whiteboard (ie. the chat interaction). This means that the AI may remember it created a file or you uploaded a file, but it doesn’t have access to it unless you upload it again.
This can become frustrating. Here’s a several quick lessons to relieve your stress:
Lesson 1: Feed the AI your files relating to the topic you are working on. The more you give it, the more it can help you.
Lesson 2: Any files updated by the AI or files generated by the AI you need to download and keep for yourself and your next interaction with your AI on the same subject.
Lesson 3: If you are using your AI for more than casual learning of information and working on real projects of importance to you, it is worth investing in the file library feature your AI offers.
Feeding your AI is what makes it grow big and strong. However, it’s so much like that child you raised. You can feed it, but after a little while you will hear “Feed Me!” again. You can give it what it needs to do its work, but it may not keep track of it and you’ll have to give it to your AI again. Feed, repeat. Give what it needs. Give again. Yep, it’s like raising kids.




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