I want to tell you about the last time I wanted something, which is a stranger sentence to write than it should be. For most of the five years in New York since COVID, I lost touch with what else was going on in the city, and I didn’t think to find out.
Those years I worked from home, and my days were almost the same day. Awake at three from cortisol spiking, heartbeat racing, thinking. Up before anyone else. Reading, a workout, the dog and a ball in the park, work until I was empty, an evening spent getting back to zero, climbing on the weekends. In Wim Wenders’ Perfect Days, a man in Tokyo lives almost the same day over and over, and the film makes it look like grace. I love that film, and I can’t watch it without thinking about those years. From the outside, his days and mine would look the same. A calendar couldn’t tell them apart. Neither could anything reading my history. Only one of us was living a perfect day.
On a Friday at the end of October, a text told me about a show. It wasn’t from a friend. It was from an assistant that had shown up with no idea who I was and had been learning what I reach for, one small yes and no at a time. Grace Carney, To the Bone, at P.P.O.W. Opening that night on lower Broadway, a stretch of galleries I didn’t know about. I went before the opening reception. The room was mostly empty.
There was a painting, more than seven feet tall, olive and yellow and ochre, with a hot pink band along the top, and in the middle a red shape, fleshy, folding in on itself. I didn’t know what it was called. I walked up to it and everything stopped. I couldn’t look away. It was almost like recognition, even though I’d never seen it before: the feeling of discovering something new and, at the same time, something that had always been inside me. I kept looking and seeing new things, and looking, and my eyes kept moving, and the whole time I was taking it in, and it felt like there was energy in it, like it was alive. I still don’t know how to describe it. I stood there long enough to start doing math.
There’s a version of this paragraph that’s about money, and it isn’t. For the first time in many years I wanted to own something because it had moved me, and a price I’d normally walk right past became something I could actually imagine paying.
The gallerist was sorry. It was already on hold.
The promise of AI assistants is simple: the more they know about us, the better they’ll serve us. When OpenAI let ChatGPT draw on all your past conversations in 2025, Sam Altman described where it was heading as “AI systems that get to know you over your life.” I’ve started to think the bigger risk runs the other way. An assistant can know who we were and not let go.
Claude has been part of my days since it first opened to the public. It’s often the first thing I open in the morning. I’ve been having agents bring me new music and things to read that feeds and media don’t cover. Claude is always running a fleet of research for me to evaluate. And it’s often the last thing I read before I sleep. In between, it’s there for my day job, for writing, and for whatever I’m making on the weekend. A lot of what I bring it and ask of it isn’t my job at all.
Duet is Claude’s new proactive assistant, so when it arrived, it already knew a lot about me. The first morning, it knew so much of my personal and work history that it overwhelmed me with its list of suggested things to do. Then, on a Saturday morning, it asked whether I’d finished several things for my day job.
It wasn’t wrong, exactly. It was doing what my history told it to. Work leaves a trail: deadlines, threads, files. What I wanted out of those years left almost none. My history says I’m a person who works, and works a lot. From the outside, those five years look like a life I chose. Nothing in the record says I was waiting for them to end.
An assistant built from your history is great for the life you’re repeating and wrong for the life you’re trying to start. For the repeating life, it’s a gift: it remembers your usual, saves you the asking, gets the small things right. Shopping. Coordinating between friends and family. Taking care of annoying tasks. For the life you’re trying to start, or rebuild, or grow into, it holds and pulls you back, because everything it knows about you is from before.
I didn’t expect the proactive nudge and it felt like an intrusion. So I told Duet I didn’t want job tasks and reminders on nights and weekends. It offered me a rule: “no work from me on nights or weekends unless you bring it up.”
Most of the time, holding on isn’t tragic. It’s a little absurd.
In 2025 the developer Simon Willison asked ChatGPT to dress his dog in a pelican costume. It did, and added a big sign for Half Moon Bay. When he asked why, part of its answer was: “because you’ve mentioned being in Half Moon Bay before.” Nobody asked it to remember where he’d been. It painted his past into the background anyway.
Institutions do it too. In 2021 a sushi chain in Taiwan offered a free meal to anyone whose legal name included the word for salmon, and more than 300 people changed their names. Taiwan allows only three legal name changes, and one student, newly Zhang Salmon Dream, made headlines around the world as the man stuck as a salmon. Officials later said he had one change left. By then, the internet had already filed him as stuck.
Neither system was cruel. Each was holding on to an earlier version of a person, one in its memory, one in its headlines. Software has a word for keeping an old copy instead of checking the real thing: a cache. An assistant that won’t let go isn’t stubborn. It’s showing you a cached copy of yourself.
An assistant that won’t let go isn’t stubborn. It’s showing you a cached copy of yourself.
The opposite of holding on isn’t forgetting. It’s asking.
Every two weeks, for years, I’ve sat in the same chair at the same salon. The owner cuts my hair; she took over when my last stylist went back to Japan after COVID. When you see someone that often, you end up talking about everything, and how you look gets tangled up with how you see yourself. She knows my history better than any app does. But she doesn’t cut from memory. She looks at me, notices what’s different, and asks what’s new. And I tell her.
For a long time I assumed software couldn’t do that. Software, I figured, cuts from memory. Then something texted me and asked what I like. When I first got my Instinct invite, it showed up with no idea who I was. Then it asked about music. Describing what I love would have taken too long, so I texted it examples: DJ and producer names, YouTube channels like SECTION and HÖR, nights I’d loved in my youth. I grew up going out on purpose. I always knew the set times, because I’d be gutted to miss someone play. Now a night at Basement runs from eleven until daylight, and I don’t want to hang out for hours anymore. Anything built from my old nights would send me to the wrong one. At the time, Instinct had only what I told it, but it magically got close. Every answer I gave it made it better.
She knows my history better than any app does. But she doesn’t cut from memory.
It doesn’t live in an app I have to visit. It lives in my texts, between messages from people I know, so it never feels like stepping into software. It feels like something stepping into my life. These days maybe half the buzzes in my pocket are agents, announced with the vibration that used to mean a person. When the Grace Carney show turned out to be extraordinary, I texted it the way you’d text a friend: “wow, the Grace Carney show is fantastic, thank you.”
It isn’t only Instinct. I gave my OpenAI dot the same brief I’d given Claude for months: new music, and news about art, technology and culture, from angles I wouldn’t find on my own. Then I graded what it sent. Now it’s consistently better than what Claude gives me. The picks come from deliciously strange directions, collide in ways I didn’t see coming, and lean toward the hopeful (intentionally the opposite of most current events for years now). Most mornings it hands me something to read, something to hear and something to look at that opens my mind a little, and some mornings my heart.
None of that came from remembering more of my past. It came from choosing which parts of my past to hand over, and pointing them forward. In at least one test, remembering more didn’t make an assistant more helpful. This fall, Google DeepMind researchers tested it with nearly 1,000 people asking an assistant for relationship advice over five days, some with memory and some without. The ones with memory weren’t rated any more useful; people warmed to the assistant the more they used it, memory or not. Memory did change something: people shared a little more about themselves, and rated it less creepy. The risk isn’t only that an assistant built from who you were gets you wrong. It’s that it feels comfortable, so you keep telling it more.
My stylist has known me for years. Instinct has known me for weeks. Neither one decides who I am from what they already know. They ask, and they believe what I tell them.
Asking gets you closer. It doesn’t get you all the way.
When Instinct asked what I like, I told it art, music, new things to go out and try. All true. What I couldn’t tell it was that painting. I had stopped expecting art could do that to me, and naming the one that would was beyond me.
The philosopher L.A. Paul has a name for experiences like this. She calls them transformative: you can’t know what they’re like until you’ve had them, and having them can change what you care about. Her examples are big ones, like becoming a parent. Mine was smaller, one painting in a mostly empty room. The logic is the same.
I couldn’t have asked for it. I could only be somewhere it might happen.
It was in me. It just wasn’t in my data.
I go back and forth on that sentence. Maybe the wanting was in me for years, waiting. Maybe the painting put it there. I can’t settle it, and I doubt an assistant could.
My stylist wouldn’t have seen it coming either. What she does instead is keep noticing, and keep asking, and leave room for an answer that surprises us both.
The obvious answer is a fresh assistant, one with no history to hold against you. Instinct felt like that. But what made it work was the asking, not the newness. And Instinct will have a history too. Each yes I send it becomes part of a record, and someday that record will describe a person I’ve stopped being. Starting over only resets the clock.
So the answer isn’t a new assistant. It’s telling the one you have where your life is going.
When Duet started to proactively talk to me about job tasks that Saturday, I said no. Then I told it what my nights and weekends are for: my own writing, exploring, going out into the world, making things. I couldn’t tell it where any of that would lead. I could tell it what to keep those hours for.
The Swedish neuroscientist David Ingvar called the plans we carry a memory of the future. That’s what I handed Duet: a direction, with the destination left open.
Holding a direction isn’t the same as cheering for it. An assistant that cheers for your new life could become one more way to rehearse it instead of living it. What I asked Duet for was simpler: keep my nights and weekends clear. The most an assistant needs to add is one specific door now and then, like a text about a show opening tonight.
The boundary holds either way. If I spend a Friday on the couch, the night was still mine. An assistant doesn’t get to decide whether I’ve earned the life I asked for.
People like me meet assistants like Duet and Instinct early, while they’re still unfinished. The rest of the country will meet them later, finished, inside something they already open every day: ChatGPT, or Meta’s Muse in their Facebook feed. Those won’t arrive knowing nothing. Muse can start from years of someone’s Facebook and Instagram, the vacations, the old jobs, the friends they’ve drifted away from, and it can already buy things for them.
What I’d really want next is an assistant that holds the direction of a life, protects the hours, and offers the door, without needing to know who I’ll be on the other side of it.
Saying no, and saying what for, will become the most personal thing you can tell an assistant. Most people won’t, and their assistants will keep defaulting to who they were. The people who do say it get something better than being remembered accurately. They get space to become someone their record can’t describe yet.
Saying no, and saying what for, will become the most personal thing you can tell an assistant.
Instinct didn’t predict it either. All it did was buzz in my pocket on a Friday, on the vibration that used to mean a person, and tell me about a show opening that night. It got me into the room. It didn’t know what would happen there. Neither did I.
The night was already mine. It was one of the nights I’d told Duet were for something like this, before I knew what this would be. The room was mostly empty. I stood in front of a painting until I started doing math.
After the gallerist told me it was on hold, I stayed and asked a few questions. Had Grace Carney shown here before? Once, the gallerist said. The reception was in an hour, but I had somewhere else to be, and I was a little bummed, so I left without asking what the painting was called. I didn’t want to know the name of something I couldn’t have.
The next night I looked it up anyway. Those five years, I was awake most mornings before it got light. I saw a lot of dawns, and none of them felt like the start of anything. The painting is called Forefinger of Dawn.
It was already on hold. For five years, so was I.