Ten Tips—An AI Exit Interview

Don't think twice ...

I told [Steve Goodman] it was not the perfect country & western song because he hadn’t said anything at all about mama or trains or trucks or prison or getting drunk.

David Allen Coe

The following is an excerpt from a very recent interview.

Q. During the break there were some students who said your last tip about [artificial intelligence] sort of sounded like you were calling it quits, and it turns out, as you said to them on break, you actually are.

Yep. “Stepping away from the practice of law” is the phrase I’ve settled on. Where I’m bound, I can’t tell. Like at a really deep level, I just don’t know. Becoming more committed to that philosophical stance.

Q. Are the AI things you wrote about part of it?

I don’t know! [gesturing] [laughter] Probably not a big part, but I don’t know. I wrote a tip that noted how the left brain is the “bullshitter” and will always have a story.

Q. What were some of your professional highlights?

Clerking. I also worked closely with two wonderful partners who went on to become ambassadors, and my #1 mentor did even better, splitting his time between Malibu and Montana. Some good friends have become judges. I had a wild case that led to a Posner opinion, and another that led to an Easterbrook opinion. Both of those meant a lot. I had a big role in Ketanji Brown Jackson’s first MDL as a district court judge, and she listed me as an attorney reference when she got picked for the Supreme Court. That was cool. I argued before Amy Barrett when she was on the Seventh Circuit. Cool. All of my Montana stuff—five jury trials, then later the dinosaur case I had. I also had three arguments in two days before Alex Kozinski and that was [gesturing] [laughter]. In close to 27 years as a lawyer, I’ve worked with a lot of people I really loved, and I hope they know that. And I still do work with people I love. Not all of them, obviously. But even with things I love, I love appellate arguments, and my last three, which I loved, I asked myself, “If this were the last one, are you ok with that?” And I was.

Q. So why are you “stepping away from the practice of law,” in your words?

The left brain would offer up things: people, situations, disappointments, boredom, regrettable office space decisions, various other things that unease you. Then there’s a flip side: what am I missing out on, or at risk of missing out on, or worse back pain, or death. It’s a lot of stuff on each side, even assuming that’s the stuff. So take all that and mash it up and sort of sculpt it [gesturing] [laughter] and when I’m forced to eat those mashed potatoes shaped like Devil’s Tower . . . well . . . [gesturing] [laughter] I throw up.

Q. That’s visceral.

I’m not kidding. I literally puked. I’ve puked at work, and thinking about work at home, and barely saved myself from puking several times, and other stuff. So there’s left-brain, “Here’s a story why I’m doing X,” and then there’s right-brain visceral reality that’s a bit of a mystery but a signal that’s difficult to miss.

Q. So this is a real mental health thing or even a physical thing at this point?

What you just did there with “mental health” bugs me. It sort of implies that if I had “mental health” I’d keep doing it, and that it is some loss of “mental health” that makes me step away. Or if I got “mental health” back, I’d return, like someone coming back from surgery.

That’s not how I feel. I’m healthy. Actually, can I read something? I found this in researching for the last tip. It’s a quote from Ted Kaczynski [gesturing] [laughter]. I can get it on my phone. Here. “The concept of ‘mental health’ in our society is defined largely by the extent to which an individual behaves in accord with the needs of the system and does so without showing signs of stress.” You were sort of adopting the view Ted describes there.

Q. Do you think that fit Ted Kaczynski’s situation?

No, and that’s why I left it out of the last tip. In reflecting on Ted—which, by the way, when I was in high school in Montana I went elk hunting with my dad and we stayed at a motel in the remote town of Lincoln, this was before Ted was captured, when he was there and out and about. I find that kind of chilling. Also, I remember watching the movie “Heathers” at that motel. Always stuck with me and stuck together. “Heathers,” Winona Ryder, Unabomber, town of Lincoln. Strange things.

Anyhow, Ted left the system. He went full Walden, but it didn’t make him happy. Didn’t give him “mental health” [gesturing] [laughter]. I suppose he would say that “the system” was still out there and affecting him. He set wires at about neck level because of kids riding motorcycles near his place. He would have decapitated them. Expansive view of “the system.”

But once you retreat to the woods—motorcycles aside—you’re pretty much out of any system that was bringing you down. So now if you’re stressed out and paranoid and wanting violence and death, it’s probably something else.

Q. How is the system of big law firms these days?

Big. [gesturing] [laughter]

Q. Too big?

I definitely see it getting smaller or consolidated.

Q. Because of AI?

I think it will be devastating.

Q. Not just revising or drafting briefs?

Not even close. Lawyers got where they are because they can read and understand boring and complicated stuff. Can solve logical puzzles about it. They can draft it. AI does all that lightning fast. And there is an enormous database of it. Probably the only thing that prevents catastrophic destruction of large law firms is that the database of existing documents hasn’t been turned over to ChatGPT, inside law firms or at the clients or behind the pay walls of e-filing systems. But once that changes, it’s over. And I expect that before the robots take over lawyers will be functioning more and more like robots.

Q. You speak of being a lawyer to all of these students as if it’s not creative. Is there nothing creative? No craftsmanship?

I think craftsmanship or being an artisan is a good analogy or model. Michel Houellebecq’s novel, The Map and the Territory, meditates on artists and artisans. They used to shape rock, wood, clay, glass, and fabric for the things we use every day, but also fancy things that we would definitely call “art” or “creative.” Like an old church or fancy furniture or tailored clothes and hats. But now those things are cheaply made with machines, so cheap they can travel an ocean and still be cheap. And things that once seemed like “art” or at least exhibited a high degree of craftsmanship are just well-worn designs for the machines. They’ll even paint you a Van Gogh.

Law is no exception. There was craftsmanship and creativity. But it’s in the database. Some judgment and creativity and craftsmanship will remain. But that’s not the bulk of the work. Large law firms need a hulking mass of boring work to survive, like Olympic-sized swimming pools full of mashed potatoes to be eaten. It will mostly vanish. Just like tables and chairs made by artisans. And I don’t think there will be any artisan, Shaker, Amish legal services attractive to wealthy people or hipsters. But the machine doesn’t go to court or meetings, so there’s that.

Q. Courtroom lawyers are like massage therapists post-AI?

Perhaps. Though I tried a new-fangled massage chair in the Dallas airport, and I’m not sure about the survival of the massage therapists.

Q. Like real therapists then.

Not sure about that either. I used ChatGPT to make a list of movies I should watch. It recommended the movie “Her,” where a guy falls in love with a very advanced, personalized smart phone assistant like Siri. Seemed entirely plausible (and ironic, maybe even flirtatious on ChatGPT’s part). Experts say the key to therapy is trust, not so much the modality of the therapy. Most people never part with their phone, take it to the bathroom, keep it by the bed, have thousands of photos, emails, texts, and their music and videos on it. That is all very manipulable, and creating some trusting relationship seems plausible.

They’re also studying having people take drugs like MDMA to assist therapy. It’s to establish that feeling of trust and openness. Who knows, we could all wind up taking drugs and talking to our phones or with some VR helmet for our “mental health” [gesturing] [laughter].

Q. So what’s stepping away look like for you? What are you going to do?

The first thing was getting comfortable saying “I don’t know” to those questions. That was difficult. I practiced law for large institutions for nearly 30 years and mostly did the next sensible, career-advancing thing. And now? [gesturing] [laughter]

Q. Do you have a bucket list? Maybe you’d use ChatGPT for that?

I did do something like that on travel with ChatGPT, and then I asked it to estimate a price. It was a lot lower than I would have guessed. Kind of put front-and-center that price was not my barrier. It was [gesturing] [laughter].

If I had a bucket list, it would mostly be learning or creating things. I have two Chopin pieces at my piano now. I want to learn them. Stuff like that.

I’m going to write. I’ll keep posting on Substack. See where that goes. Writing on Substack has been an important change for me. I hope to do a lot of driving. I want to drive the length of the Pacific Coast Highway. I’d like to drive through the desert to Las Vegas and across southern Utah and Colorado. It would be cool if I could take my dog, but I’m not sure about that.

Q. Why are you unsure about that?

My dog is a nervous, adopted pit bull named Dr. Gonzo, and the car I want to drive is a Porsche 911. My dog would have to sit in the front seat, and I would need to be careful.

Q. You have a Porsche 911? What year?

The one I want to drive is a 2024.

Q. You have more than one Porsche 911?

Not every path to “mental health” involves living in the woods, if it ever does.

Q. What do you mean by that?

[gesturing] [laughter] Some part of me just knows. Like some part of me knows I should be writing, driving the Pacific Coast Highway, learning Chopin, and so on. And eventually knew that I was in the wrong place and needed to be doing other things.

Q. You have two Porsche 911s because of some feeling guiding you like The Force, aliens, or the Paraclete?

Perhaps. I don’t know. Or maybe I gave ChatGPT all of my tips and other Substack posts, some bio info, and told it to create an interview with the author and set it as if the author were being interviewed in front of students, that the author was talking about quitting his job as a lawyer at a large law firm, to make it fun but philosophical, to have bracketed places where there were undescribed gestures and laughing, and to work in the following: subtle allusions to On the Road, Travels with Charley, Fear and Loathing in Las Vegas, The Three Stigmata of Palmer Eldritch, “Close Encounters of the Third Kind,” “Star Wars,” and “Bette Davis Eyes,” as well as explicit references to Chopin, “Heathers,” Porsche 911s, “Her,” throwing up because of work, a pit bull, cool massage chairs in the Dallas airport, drug-assisted and AI-assisted therapy, and The Map and the Territory. Would you believe that’s mostly what this is?

Q. I really don’t want to believe that’s what this is, or that I’m just some creation of another intelligence. It would be like seeing your face turn into some kind of robot all of a sudden. It would be unnerving. But I don’t actually know.

I don’t know either [gesturing] [laughter].

Well, I was drunk … the day my mom … got out of prison. And I went … to pick her up … in the rain.
But before I could get to the station in my pickup truck,
She got runned over by a damned old train.

And I’ll hang around as long as you will let me
And I never minded standing in the rain.
You don’t have to call me “darling,” darling.
You never even call me by my name.

Steve Goodman