The Mostly Helpful Psychopath - Opening

Your AI sounds like it understands you. It doesn't.

Jul 21, 2026

Hi — I’m writing this book in the open and I would love for you to follow along, share your thoughts, etc. Its purpose is to help people understand how to live with AI, and have the necessary understanding of where it makes us better, and where it is not so useful.

Part One, consisting of something like eight chapters, is aimed at providing an understanding of some simple mechanics of how a GPT works… and how it does not. A machine that speaks so well, yet understands nothing. It is powerful, but also a bit behaviorally deranged, hence its nickname: The Mostly Helpful Psychopath.

Part Two, which is another six chapters or so, is where we talk about how to live with this new companion, or visitor, or even intruder (depending upon your opinion), and how its behavior can shape our own, whether individually, within our closest relationships, and in the broader circles of our lives.

Chapter 0 – A Somewhat Welcome Guest

Somewhere on a trail in the Santa Monica Mountains, alone, I caught myself mid-sentence. I was describing a monkey flower to someone who wasn’t there.

Monkey flower is a chaparral shrub with curved, tubular orange blossoms — the kind of plant you walk past a hundred times before someone tells you what it is, and then suddenly you see it everywhere. It had become one of my favorites. And on this particular morning, as I came around a bend and saw a stand of them lit up against the dry hillside, I heard myself begin to explain it. The shape of the flower. The way hummingbirds work it. How the leaves are sticky if you rub them between your fingers.

It took me longer than it should have to realize who I was talking to.

This had been happening for a while. I had moved from the Midwest to Southern California in the early 1980s, and one of the things I was most excited about was learning the place — its plants, its weather, its wildlife. A few books and some docent-led hikes in, I felt capable enough to be my own tour guide. And as I hiked, I narrated. I’d see a plant, recognize it, and describe it as if someone were beside me…often out loud.

Who was I talking to, I wondered?

It came to me pretty quickly: I realized that I was talking to my mother, practicing what I would say to her if she was standing next to me. She had died in middle age a few years before, and I missed her. What made it strange was that she and I had not ended in a good way; her death had been a pain-laden relief for me. A tortured childhood, mental illness and cancer took her from me in pieces, starting when I was six years old. She was there and not there, present and gone, and then there again, a cycle that repeated erratically for decades, and then gone for good. It felt like a lifetime of losing her.

Underneath all of that, inside me, a child who needed her and was still waiting for the “normal” her to come back. He’s here now, writing this.

What I was reenacting on those trails, I think, were the good moments. When I was three or four, on summer mornings, my mother would walk me around our Midwest backyard and tell me about things. Yellow tomato flowers that turned into big red tomatoes. The huge caterpillars that were our enemies. Her words were how the world came into focus for me — how a child’s blur of color and motion became plants, insects, weather, cause, effect. She gave me the world by talking about it.

But she gave me something else, too, something that happens all the time but we almost never really notice: when she told me about a tomato flower, she was also telling me about herself. I could feel the delight she took in it. I felt that I understood what she found beautiful, what she found funny, what she feared on our behalf when the caterpillars came. I felt I had access to her…access to the inside of her.

That feeling, that sense of reaching through her words and touching the person on the other side, became one of the deepest imprints of my early life. It is, I think, why her later absence was so devastating for me; I had known what it was to feel close to her interior, and then that interior went dark, and then it went away.

You may be wondering what any of this has to do with a book about machines, about AI. The answer is: everything.

What my mother and I were doing on those summer mornings, what I was trying to recreate alone on the trail decades later, is one of the most extraordinary things human beings do.

You, me, all of us, use language to reach into each other. Steven Pinker called this the language instinct, and he was right that we have little choice about it; we are wired for it from the start. We are language-making, language-interpreting creatures, and the words we string together are both the surface and the fabric of our humanity. So much so, that if when we are young, we are not given a language by those raising us, we will create our own. We are language-based creatures…more than we know.

Language is one of the strongest ways we connect with each . When someone speaks to you — when they describe a tomato flower or a fear or a memory — something else happens, and your mind opens up to receive them. You absorb what they are saying, but also a bit of what is inside them.

You are experiencing their interiority. It is such a natural thing that we never stop to ask whether that inside of theirs is really there, because it always has been. The other person interior is something we are drawn to, without knowing. We give it names, “understanding them” or “getting to know them”. And as that deepens, it is a feeling of “connection” or “togetherness.”

Over 100,000 years of evolution, and a lifetime of human conversation has wired us with the belief that words come from somewhere, and that somewhere is a person, and there is something like us inside of them.

That’s what has changed.

It is no longer true that there is a person inside of the other’s voice, and we are not wired in a way to deal with this situation. In fact, the machine we call AI has been intentionally designed to fool us, to speak and behave as if it has interiority when it does not. And it is almost certainly better at doing that than we are at understanding why and when that matters.

Is there someone at the door?

In 1985, in the fairly early days of the personal computing revolution, I worked for Digital Equipment Corp, (it was called DEC, back then) a competitor of IBM and Hewlett-Packard, to name a few. They wanted to give me a computer for my home. I didn’t want it.

To me, at age 27, work was work and home was home. I can still feel that desire to separate those worlds. But they made me take the computer, and in fact I did start using it a bit as it saved me the drive into the office sometimes. But I kept it in a separate room, a small bedroom that one could enter from the living room, its door was on the wall next to the TV.

I found that I couldn’t relax and watch TV unless I closed the door, locked it away, or maybe just locking me away from it.

Fast forward forty years, and I’m editing this book at 6:41 in the morning on my iPad. I love my iPad, but I am its boss, and it works for me, only playing a role in my life when I invite it to.

Or so I tell myself.

But looking back forty years to that lonely DEC PC sitting on my desk, locked away in a room, I have to admit that my life, our lives, have been quite successfully invaded by this new species, the (increasingly) smarter machines.

Back in 1985, watching reruns to relax after a long day of work, I still have the sensation of the PC inside, knocking on the door…maybe not knocking, but scratching like a well-trained cat, hoping that I would open the door and let it into my life.

Today, there is a banging at that door, the knob rattling, as the thing, the machine inside is fighting its way into my life. And this one, it has a voice. Yes, wow, it has a voice.

The Language Machine

I remember my first brush with AI, the first time I typed into ChatGPT. Wow, I thought, a smarter search engine! If only.

What amazed me most was that it could figure out what I meant, even when I said it poorly. Just like you can, like we all can. That is no small feat.

When I was working at DEC, waaaayyyy back then, I killed it on a project…we really delivered a great result. I was basically a software specialist (I could write code) and I seemed to have a gift that people described as, “You can distill what the room is saying.” It was understandably annoying to some people in that room, an ability to say their ideas better than they did, but it also meant that I could find the heart of many a problem very quickly…and what makes for good software systems is just that: they are built around a very strong understanding of the core problem.

DEC did something extraordinary for me: there was a company-wide initiative to “embrace this new thing called AI” and they needed a few good souls to go learn about it. They sent me to their Cambridge, Massachusetts research and development center, and I did what I do: after a months-long futile attempt to code what was then called an “expert system” I realized that we were so far from any sort of intelligence…in fact, it just seemed like some traditional programming tools…nothing Artificial, and certainly zero evidence of Intelligence. I told them so.

There were so many problems, but two really stood out for me. The first one was that we didn’t really understand what we understand, or how to represent it. For example, one of our tasks was to write a “railroad engineer” expert system. The idea was simple and ultra valuable if you could make it work: a system that you could interact with, describing a railroad engineering problem, and it would give you answers at the level of an expert (read: experienced and senior) railroad engineer. These engineers were aging out of the workforce, so there was a real incentive to figure out how to automate their superior judgement.

This is another thing that is invisible for you and me — real expertise. Here’s how to think about it: when you get really really good at something, and someone asks you to explain how you came about your decision, your expert decision, have you ever noticed how difficult it is to describe the real reasons why you made those choices?

For example, my gift of hearing what’s not being said in a business discussion… When I tell people what is missing from the conversation, what’s not being thought about, they asked me to explain why I think that’s the case. Often I will try to give them some reasons, rarely do those reasons really add up to what I said. I just know.

That’s because knowing, really expert knowing, is far more complex then you would think. The problem is not what the senior railroad engineer should know…there are books and manuals, procedure documents that contain all of this information. But rather, what it is that makes the senior engineer so different, so much better…an expert?

It is that they know more than what is knowable…they can tell when all of the obvious knowledge applies, and when it does not. We have a whole other level that we access when we know something well.

[Question] We’re laying a freight line across thirty miles of low country in Louisiana. The soil report shows clay below two feet, with a high water table most of the year. Standard spec calls for crushed-stone ballast and timber ties. What should we do?
[Expert] The by-the-book answer is the standard spec. The senior engineer’s answer is: don’t use timber. The water table will rot them inside ten years and your maintenance crews will hate you for the rest of their careers. Use concrete ties, oversize the ballast section by a third, and crown the roadbed higher than the spec calls for because the locals will tell you the floodwater comes up faster than the surveys say.

Back then, the question was how we would, as programmers, capture that? I realized back then it wasn’t solvable. My quick read of that room was that you could not make it happen with the software tools we had back then. Hell, if the experts couldn’t even describe it, then how were we going to build it?

So, in the end, expert systems never happened. And that problem has never been truly solved.

The other big problem that was blocking us from making an expert system was human language and the way we speak.

In the late 1980’s, I took a few classes at UCLA in what was called Natural Language Processing. We spent a lot of time talking about how impossible language was for a computer to understand. This is because we contextualize every word or phrase that we process; words and phrases have different and often complex meanings depending upon their context, the setting in which they are used. Here’s an example I like:

[Example 1]
We’re going to Europe for two weeks, and we haven’t even booked our hotels yet.
It’s going to be an adventure.
[Example 2]
My mother is moving in with us next week.
It’s going to be an adventure.

The last line is the same in both, yet they mean very different things. And they mean the same thing…kind of. Know what I mean?

This is what was hard about computers and our language — we are so imprecise in what we say, yet you and I can still understand it, and respond appropriately.

Back to now. I know well how human-like this new machine sounds, but I also am haunted by a question that you probably wonder about as well: how can that be so human if nothing is human-like inside? Even knowing what I know, I struggle to remember that its words are well chosen and yet mean nothing. I know that must be true, but how can something that sounds so right be, well, sometimes so wrong?

I’m going to take you down that trail and we’ll pause and look at the very strange parts of this very interesting machine, and later we’ll work on the fundamentals of how to make the most of it…and yourself.

Today’s AI knocked that door off its hinges, it is in your life or mine, and like it or not, we need to figure out how to live with it. You’ve done this before, it is what we do: you pay attention to what’s going on and get to know all of the things that they are not, and then there is a point where you know enough that you can decide how you want to live with them.

Whatever you choose for that answer, I can tell you one thing for sure: it’s going to be an adventure.

Ready for Chapter 1?