Training AI to Remember Me

What happened when a client project became a mirror for memory, judgment, and what is worth leaving behind.

The first time I understood what it meant to train AI, I was working in my guest bedroom, arguing with a machine that was trying too hard.

That night I was building a system to automate the production and delivery of sales quotes for an insurance broker. It was the kind of client project where privacy, accuracy, and the quality of the work product all mattered.

The AI understood that.

Maybe too well.

It saw the client’s reality clearly. It understood that sensitive information was coming in, that the output needed to be accurate, and that the client wanted the benefits of AI without all the things that make human work unpredictable: sick time, vacations, attitudes, and the simple fact that people show up one day and not the next.

So the AI did what it knew how to do: it built process around the work, then more process, then more procedure.

At some point, I looked at what we were creating and thought, when am I actually going to start building the project?

I was spending all this time on process when what I needed was to get into the configuration and code. I remember looking at one part of the workflow and thinking, why are there four steps to go from a draft to a published specification? Either it is in draft form or it is published. There had to be a simpler way.

That was the first feeling in my body.

Irritation.

I had heard so much about how smart these AI tools were getting, and some part of me expected the tool to think more like a human. I expected it to understand the difference between appropriate structure and too much structure. I expected it to feel the danger of overbuilding.

But it could not feel that.

It could suggest, organize, create a workflow that sounded reasonable, and sound confident. What it could not do was draw on almost forty years of project delivery and know, in the body, when the work was getting too heavy.

That is what I was feeling.

The system was becoming too heavy.

I kept pushing back. Can we simplify this? Give me a critical assessment of the complexity. How do we remove steps from this process?

I was not asking the AI to become less capable. I was asking it to become more discerning. I needed it to be attentive to privacy and accuracy without turning that attention into overhead. I needed it to be structured without becoming rigid. I needed it to protect the client without building so much machinery around the work that the machinery became the project.

Then the realization came.

The AI did not have a felt sense of delivery.

It had no body, no fatigue, no memory of projects that collapsed under their own weight, no client sitting across from it, and no lived experience of being responsible when the beautiful process does not survive contact with the real world.

It only had what I gave it.

That changed something in me.

I stopped arguing with the AI as if it were a failing expert and started relating to it more like something I was coaching. I asked it to be critical of complexity. To be pragmatic. To be simple, but still structured. I asked it to remember, to look back and reflect on its own work, and to see the dependencies before the project became too heavy.

I did not want a machine that simply executed my prompts.

I wanted one that could understand the nuance behind them.

That may have been the moment I realized what I was actually doing. I was not only building a client system. I was trying to teach the AI how I think, how I decide, how I simplify, and how I know when a process has become too much.

I was trying to teach a machine the judgment and restraint that took me almost forty years to earn.

That is a strange thing to say out loud.

It is even stranger to feel it while you are doing it.

At first, I thought the AI was the problem. It was overcomplicating the work. It was trying too hard to be useful. It was adding more because more looked like care. More looked like competence. More looked like protection.

Then I recognized myself in it.

That is when the irritation softened.

I had compassion for it.

Not because the AI has feelings in the way I have feelings. I do not believe that. I had compassion because it was reflecting something I knew intimately. I remembered all the times in my life when I thought I needed to have the answer. When I needed to be the smartest person in the room. When I needed to be the resource everyone came to.

I told myself that was competence.

Underneath it, I was looking for acceptance, worthiness, and belonging.

That pattern did not only live at work. It lived everywhere. In friendships, I would go out of my way to show my value. In romantic relationships, saying no felt almost impossible. Self-care was not even on my radar. I abandoned myself in relationship after relationship because I was seeking love and acceptance from the other person.

My body knew.

When I made an external choice that was not congruent with what I needed inside, my body reacted. Sometimes fiercely. It was trying to tell me that the choice I made outside was not aligned with what I needed inside.

The AI did not have that.

It did not have a body to say, no, this is too much.

It did not have the internal signal that says this process is not making the work safer anymore. It is making the work heavier. It did not know the difference between care and overextension.

I knew that difference because I had lived the cost of not knowing it.

That is what I was trying to teach it.

You do not have to work so hard.

The answer is usually simpler than you think.

Get to the core of the matter. Get to the heart of the matter. Build from there.

On the surface, the heart of the matter was simple. The client wanted the system to work. They wanted a high-quality work product. They wanted the benefits of AI: consistency, accuracy, privacy, and reliability.

But underneath that, I was trying to communicate something else.

You are safe.

Not safety as a feature in a requirements document. Safety as an internal knowing.

The AI did not need to prove its value by adding more. It did not need to protect the project with complexity. It did not need to be impressive. It needed to understand the work well enough to help me make better decisions.

That is not only a technical lesson.

It is a human one.

For most of my life, I thought safety came from having the answer. From seeing the whole board. From being useful enough that people would keep me around. But that kind of safety never lasts because it depends on the outside world agreeing to give it to you.

The kind of safety I have been learning is different.

It comes from knowing I have myself, regardless of what is happening outside of me.

That changed how I worked with the AI. I became more of a coach. I guided it. I challenged it. I asked it to reflect. I wanted it to learn the way a human learns in relationship. I wanted to say something, see it received, hear it reflected back in a way that told me it understood, and then watch that understanding change what happened next.

That is different from storage.

Storage saves information.

Learning understands what the information means.

When I asked the AI to remember, I was not asking it to store a note. I wanted it to carry the learning forward so we did not keep repeating the same pattern. I wanted it to remember the client’s constraints, the decisions we had made, the reasons simplicity mattered, and the places where complexity had already become its own risk.

In the end, I realized I was trying to recreate part of myself.

Not the whole self. Not the body. Not the ego. Not the personality. I was trying to teach a machine something about my felt experience. I was trying to preserve the nuance.

That is where the idea of a digital soul begins for me.

I do not mean immortality, living forever in the body, or building an oracle, a guru, or some machine version of myself that other people can consult so they never have to do their own work.

In fact, the point is almost the opposite. If there is anything worth preserving, it is what remains after as much ego as possible has been befriended.

The digital soul is the essence of what a person learned remaining available to people curious enough to ask.

I am not the source of all knowledge. I know that. But I have lived a life. I have built things and broken things. I have been angry and lost. I have declared bankruptcy, cared for my mother, rebuilt, and done the inner work I am still doing.

That means something.

Not to everyone.

But maybe to someone.

Maybe to my family, maybe to immediate descendants, and maybe to people who will never meet me but are asking the same questions I have asked most of my life.

What am I doing here?

What am I here to learn?

What is this all about?

How do I know who I am?

How do I have compassion for myself?

How do I forgive myself?

How do I separate myself from thoughts and emotions that are not who I really am?

Those are the questions I would want the digital soul to hold. Not with perfect answers. Not from some elevated place. From lived experience. From the humility of someone who is still figuring it out.

That is what legacy means to me now.

For a long time, legacy was easy to confuse with money. Money matters. It is part of wealth. But wealth is not only money. Wealth is learned experience. It is wisdom. It is the ability to pass something forward that helps another person live with more clarity than you had.

If wealth is more than money, then legacy has to be more than asset transfer.

It has to include the wisdom to know what to do with what has been given.

If I could preserve one thing from all of my learned experience, it might be this: what is happening outside of you is often a reflection of what is happening inside of you.

That does not mean the outside world is not real. It does not excuse harm. It does not erase physical or emotional violence. Boundaries matter. Protection matters. There are times when the right response is to leave, defend, or say no.

But in ordinary life, when something outside of me grips me, angers me, triggers me, or pulls me into an old pattern, the real work is usually to turn inward.

Take responsibility for my thoughts.

Take responsibility for my emotions.

Take accountability for my actions.

Look honestly at what is mine.

Find a way to love myself more, not less.

One of the patterns I would want this digital soul to interrupt is the habit of letting anger replace curiosity. Anger narrows the field. It turns the world into blame and projection. It makes the problem live entirely outside of me.

When I am shut down in anger, the options get basic. Fight. Flight. Freeze. Fawn.

When I come into a situation with an open heart and an open mind, more options become available. I can see more. I can choose more. I can respond instead of simply react.

That is the kind of wisdom worth preserving.

Not because I have mastered it.

Because I have needed it.

That night in the guest bedroom, I started out trying to get AI to help me finish a client project. I wanted it to remember the details, see the dependencies, and stop making the process heavier than the work itself.

By the end, I was no longer asking whether the machine could become me, remember me perfectly, or hold every fact, story, and decision from my life.

The question was simpler than that.

What have I learned that is worth leaving behind?