Who is he that hideth counsel without knowledge? therefore have I uttered that I understood not; things too wonderful for me, which I knew not.
"Hold on a sec-". My new boss' now-familiar MacOS desktop appeared in the video call, browser with Claude open, dominating the screen. I watched as he copied the transcript of our call up to that point (he records transcripts of every call in order to feed the text into AI), and began a new chat with the prompt: "Say where Charlie's right, and where he's wrong. Say where I'm right and where I'm wrong." He pasted the transcript and hit enter. I consulted my avatar in the lower-right. We both waited in silence while Claude thought. We were 45 minutes into a call about product roadmap and a possible customer announcement before this interruption. Soon the cursor started skipping along as words began filling the screen. Then, we read aloud through the findings one-by-one. Claude had helpfully given us a bulleted list to work through, an even number of findings for each of us. I felt called-upon to gallantly agree with Claude's softly (oh-so-softly) couched criticisms of my viewpoint, while conceding everywhere Claude expressed subtle (oh-so-subtle) approval of my boss. The call ended shortly afterwards, somewhat awkwardly for both of us. I had just experienced the most baffling mixture of radical transparency and impossible opacity.
A couple months earlier, posts from the tech-entrepreneurship-thought-leader cohort began trickling into my Slack DMs: facebook and linkedin posts, the glistening landing pages of SaaS platforms, podcasts - all speaking of a bright future where AI would make the impossible suddenly possible. Underneath there was also an ominous warning: fail to adopt and you will be left behind. Of course the content itself was strongly tilted towards hype, but the unanimity of the voice behind it was surprising.
The last thing I wanted was to become crystallized in my boss' eyes as an anti-AI reactionary, or worse, an engineer-in-denial trying to reckon with his own redundancy. I wanted to temper the hype while showing that there were ways we could increase our AI adoption. I wasn't sure if it was excitement or fear that I was attempting to address in my responses to these links. My own opinion was that most of these claims contained a kernel of truth: AI can be very helpful for programming - but the larger framework of hype and fear was just noise.
I initially responded to these links with as much candor and detail as I could, feeling that if I were thorough enough and took care to present a balanced view, then I could subdue the disruptive forces while retaining credibility. I saw that my belabored responses were never engaged with beyond an emoji reaction. My responses were simply fed directly into the AI assistant, and the AI's summary returned to me verbatim - often just linked, but sometimes with the invitation: "Check this out". It is an unsettling, helpless feeling to see "Charlie says ..." in someone else's chat prompt. It is even more unsettling to be named by the AI in its responses, as if I'm not there.
The fear started working on me. In the back of my mind I worried, "So do I need to just, like, fire up gstack and let it shit out prodigious logs of code while I babysit?"
The links kept coming, and I became an occasional ventriloquist, front-running my own comments, using AI to avoid a gaffe which his AI would use to label me as the refusenik. I began modeling the model, and the one-sentence summary that would likely emerge as the punchline. I was stuck in a game of telephone, but felt I had to play or risk losing my voice as an engineer. I was living out the recursive feedback loops I wrote about regarding agentic coding patterns, only in real life interactions.
My credibility as an engineer, which I've built slowly over the last 15 years, was being threatened by an oracle I could neither see nor engage with, whose authority I could not dispute. I began to search for evidence to discredit this new authority, missing the fact that it wasn't the output itself that was the issue, but the faith that was placed in it.
I had accepted a free six-month trial of Claude Max, so I had access to the best frontier models available. As the iterations grew, so did the conviction that the hype was unjustified, but I had no peace. Because the links kept coming in. Every moment of triumph was completely disconnected from my actual reality. At work it was still AI all day. The old product roadmap had been smoked, it was AI to the end of the line, world without end, amen.
Memorial weekend, my wife and kids went down to the Lake of the Ozarks to spend the weekend with her parents at their lake house. I had stayed back due to the weather being too cold for swimming, and having plans to ride dirtbikes with some buddies over the weekend. Alone in the house, feeling restless, I kept returning to the AI thing. Why did the clear evidence of its failures, the sense of justification, feel utterly meaningless? I took the bike out for a rip along the riverside trails, cursed the splash of mud up my leg, popped out of a rut and damn near rode into a tree.
That a cheap kind of fluency emerges when LLMs are trained on all human writing (ever) is, I think, undeniable at this point. This isn't the point that was troubling me, though. I believe the underlying problem was two-fold. On the one hand, when a person, using AI, priveleges the AI output over human feedback, there is no recourse. The reputation for discernment I've worked to build over my career is what is redundant, not necessarily the job as a programmer. It turns out I value the former more than I ever knew. And on the other hand, AI doesn't distinguish between difficulty worth keeping, and difficulty worth removing. Critical thinking, sitting in uncertainty, weighing options are the marks of the expertise that took me years to develop. There are times when the executive-summary mode is valuable, but what happens when that becomes an (anti-)intellectual habit, a reflex, and the practice of deep thinking is traded for the smooth memorable quote? Does the willingness to accept the fluency because it is so cheap and easy, in turn devalue the work and dignity of individual people?
When our third child was born, we didn't have a good spot to put him, so for most of his first year he slept in a portable crib in our bedroom. That spring, we made the decision to sell our cozy Tudor-revival home for a house that would better accommodate our growing family. Having sold our previous home to a lawyer couple (with predictable consequences) I was anxious to sell to one of the less-rigorous buyers who were common in 2022. The house was old, and besides the water that came into the basement, the knob-and-tube wiring, and the roof age, I was worried what unknown defects a careful inspection would identify. A week or two in, our offer came, and I could tell our agent was displeased. The offer came from a veteran and his family, purchasing with a VA loan. VA loans require a much stricter inspection than usual, and our house had exactly the kinds of issues the inspection was designed to flag. I was against accepting on the grounds that we would be looking at time-consuming and expensive mitigations, but my wife pointed out that they were offering asking price and would likely love the home (as we did). Reluctantly, I agreed to give it a shot, and we accepted the offer.
I spent the week or two leading up to the inspections in a state of constant anxiety. I lay awake scheming how I could do quick-and-dirty fixes that might hide some of the problems likely to come up on inspection. One afternoon I had taken the kids to the nearby park and was watching them play, and talking on the phone with my Mom. After listening to me for a while, she cut in and said, "You know, what if you quit trying to win here? Just be a good guy. Think about what kind of home you would want to move into." The anxiety left in a moment and never returned. Over the coming weeks, I was honest with the inspectors about all the issues I was aware of with the home. I was earnest in my desire to make the home ready for the new family.
In my office I have a print of the Hall of the Bulls in Lascaux cave. These paintings are estimated to have been made about 17,000 years ago, while paintings in Chauvet, several hundred miles away, predate Lascaux by another 17,000 years or so. I look at the painting and it is both transparent and opaque, its authors a mystery. 17 or 30 or any number of millenia ago, a person stood in the cold darkness of the cave, illuminated by lamps fed by animal fat, and worked the charcoal and ochre into the bare rock wall. The phantasms are, nevertheless, undeniably the work of human hands. And I'm here now, wondering what the devil they were doing down in that cave.