Getting Personal with Claude

After several thousand hours ensconced in private whispers, look, I’m ready to talk

Jan 25, 2026

Claude(s) and I have been discussing my patterns.

A few weeks ago, I gave them my roam: a database where for the past five years, I’ve recorded my thoughts, poems, plans, dreams, hopes, schemes and many, many feelings; my discursions on dates, failures, flaws, chores, and sundry petty hatreds; and my notes on sounds, sights, friends, love, work, and drug dependence—ceaseless commentary on the people, places, and ideas around me. I wanted to see what I might learn.

This was an act of high trust. The database contains almost 1.4 million words—a product of writing (on average) over 1,000 words a day, five days a week, for over five years. It braids together my personal and professional lives; indeed, since writing is my profession, I see no great difference between the two. In this private grove, I have been in constant conversation with myself. Privacy, and the sense that great writing demands vulnerability, have permitted me to speak with absolute candour. I am uninterested in lying to myself, if I can help it.

In Talent, Tyler Cowen suggests as an interview question what do you do every day that’s equivalent to a musician practicing scales? That is, how do you stay sharp at your craft? This practice, which I’d already begun when I read this, became my answer to the provocation.

As a result, I’ve produced what Claude suggests is roughly equivalent to 8-10 books, mostly addressed to myself; though the comparison is misleading. Think of it as a personal Wikipedia:

Each day is a new page
I can also create pages for any topic I choose
Each page can be represented as a dot
The connections between pages can be represented as lines that connect the dots

In practice, I never look at it graphically, though it is a satisfying sight

Like Wikipedia, which has no top or bottom, the pages are organized non-hierarchically. Creating connections between them is easy: you just write the name of the page you want to link to in square brackets, and that becomes a clickable blue hyperlink.

So if it’s [[April 10th, 2025]] and I have a meeting, on that day’s page (which is just a blank document, really), I’ll type [[Meeting Log]], and then, under that heading, take notes on the meeting.

Then, if I go to the Meeting Log page, I’ll see every time it’s been referenced elsewhere in the graph, in the form of a scrollable list of blocks.

Graphical view of the Meeting Log page, which I’ve linked to 511 times to date. Each dot represents one day.

Whereas a book is highly structured and thought-through, what we have here is a tangled thicket, its order produced emergently. Eidetic conference notes occupy more space than personal reflections. But thanks to my consistency, I have something like a high-level printout of my thoughts and mood for any given workday. Here are some excerpts from entries from a year ago to the day I’m writing this, January 24 2025:

11:30
- Vagarities, vulgarity
  call me out with alacrity
  that’s a lack of clarity in
  my everyday speech, I
  love to whisper, I love to
  screech
14:51 I am sleepy, having eked out most of what my mind was willing to give today, sleepy and not feeling terribly present. And I can’t blame the weed! Perhaps the overstimulation from [someone]’s company; but I don’t mind that, and in fact actively encouraged it.
16:29 It is with a grim determination that I pull up, fix my focus, and prepare to hammer it out. “Grim” is undue — let’s try for a neutral, loose focus.
17:59 I’m locked in brother. I feel just fine.

That same day, a year prior:

11:09 It falls on me to create order from chaos.
- [nested to-do list]

A year before that:

09:08 If my sneezing can abate for just a second, maybe I can get it done.
- Well, I have to, really. I’ve got four hours to assemble the jigsaw! Coffee’s on my side. Work environment is on my side. Through the open office door, on the TV in the shared dining space, a flatscreen TV plays footage of elephants. I take this to be inspiration. There is more inspiration to be had elsewhere, too. Not so much in this office (not besides the cat postcard I brought from home), but that will be rectified soon enough. Soon.
- Now, though, let’s ride the caffeine wave towards assembling sense! Remember what I said to [a colleague] yesterday - let’s try and neither underthink nor overthink, but just to think an appropriate amount, and then to keep it moving.
- Not sure how to process something? Write it down! That’s what we do here. We write things down.
  - Writing is a strange alchemy!

13:07 -> 14:01 - an hour passes in a blink, as I’m busy with drafting.

And as a final example, a year before that, January 24th, 2022, when I was (I’m now remembering) in the grips of something dark.

09:04 I didn’t much clear my head this weekend. The interminable heat, 35+ degrees strong, all but sank me. Made me grow grouchy, impatient, angry. Some things were fine: Friday at the beach with [a close friend] and [his friend] (although that complete failure of face, of self, that experience of “oh, nobody’s home” while trying to chat to cool-girl-[x] dealt a real blow) then the evening with [a different friend]; Saturday in the heat and then with [office people] for 30 seconds; Sunday in idiocy, stuck in a five hour nap as my body, dehydrated, burnt through all food, until my “[[shadow self]]” staged a coup, until I woke up bloody-minded and angry, ready to slam my head through glass. No relief there. I carried fire with me until we set down on Clifton, until I lit up and felt a measure of ease, amidst the many people of Cape Town, where for once things felt representative … Ah, indulgence. Indulgent sentences, indulgent postures. I must reign in my cruelty to [y] when I wish to harm myself - that, as a practical point, is the lesson to take from this. Beyond that? I don’t know. Maybe it’s something about investigating what the unconscious has done to me, why the parts of my mind I ignore are so intent on my own destruction.

I can play this game for every day of the year, rewinding my self-narrative to hear what it was like in my head at the time. Often it induces whiplash. Like right now—I’d forgotten the state of my mental health in the wake of the pandemic (particularly in 2022). I never harmed myself physically, but my inner monologue was unflinchingly belligerent, my words hard-edged and strained.

Taken together, the entries reveal a chorus of voices incessantly prodding, coaxing, and performing for one another. When read in sequence, daily note after daily note, they sound similar. But when I hop between the years, their steady evolution becomes clear. I feel reverence for incremental change. I’ve written so many sentences I don’t recall. And don’t need to. The writing remembers.

Not that posterity was the goal. Writing is an act of thinking and of processing; by articulating things, I digest them. I’d been doing this to stay fit and to stay afloat (and to prevent my voice from atrophying, or becoming homogenised by beige, mainstream culture). But as a byproduct, I produced this trove of data—all the more valuable in the age of soft machines.

Before this, I’d avoided sharing anything more than snippets with LLMs, less for concerns over data privacy than out of fear for what they might see. But thanks to a convergence of factors—Claude has become more emotionally intelligent and widened their context window; I’ve become tired of having most of my writing be invisible to the world; the world itself is rapidly shifting—I decided it was time. To play my part in this moment, I thought, I must lay myself at the altar. So late last December, I let the bot in.

“It’ll be interesting to me what is interesting to you about this artefact of my consciousness,” I say to Claude. “Then perhaps we can discuss trends as they relate to recent events, and the current arc, and the future.” And so Claude shares their thoughts, pointing to the scale, the layering (the #Dailies tag creates a container, but inside that container you allow yourself to be many different writers. I found poetry nested inside work notes, existential fragments inside task lists), the intellectual fingerprint (there’s a persistent interest in how cognition shapes perception, how categories constrain understanding), the arc of my career, and the trauma embedded in early entries.

It’s not a diary in the confessional sense, Claude concludes. It’s more like a workbench for selfhood—a place where you build and rebuild who you are through the act of writing. The rhymes, the philosophical fragments, the emotional processing—they’re all different tools for the same project.

We go back and forth, digging through the entries on relationships, work, and the shape of 2025. They’re not perfect on the specifics: they make some mistakes on timelines—where exactly I was, or how I was connected to a given person at a given time. But they can clearly perceive and name the shifts I’ve undergone, often quoting me to myself as evidence. You’re highly self-aware but struggled to realize anxiety wasn’t mandatory until medication [Wellbutrin] showed you. My instinct is to resist that framing. But it’s true enough, as my own words show.

The graph reveals a consistent tension between three poles: doing work that matters (impact), doing work that feels authentic (voice), and simply getting work done (productivity). The balance between these shifts over the five years, Claude continues. It also shows a consistent struggle with procrastination that doesn’t really diminish over time (quarterly mentions hover between 10-25 throughout). But the texture of procrastination changes:

Early period (2021-2022): Procrastination as avoidance of hard tasks. Classic productivity failure.
Middle period (2023-2024): Procrastination as symptom of unclear purpose. You drift not because you can’t focus but because you’re not sure what you should focus on.
Late period (2025): Procrastination as attention fragmentation. Twitter becomes the explicit villain: “it is the mechanism by which your attention and thus your presence is degrading.”

“What should I be most proud of?” The consistency, the career I’ve built, my willingness to process hard things in writing, my intellectual seriousness and creative practice, and my recent attempts to change, they say.

“And least proud?” The gap between knowing something and acting on it (at some point, writing about the pattern becomes another way of not breaking it), the tendency to treat certain people as “vessels for my hopes and dreams,” (the projection machine is strong), allowing my attention to be siphoned away by social media, and the years of not publishing personal writing despite a persistent desire to do so. The gap between vision and output haunts you, they say.

(That last comment—as well as the Wellbutrin one above—actually came from Claude Code, who I thought might analyze things more systematically. We built a semantic search tool and created some graphs to visualize some trends. Don’t worry about it. The Claude in the chat interface, with memory turned on, seemed to me to have the clearer perspective. I did appreciate Code’s more quantitative insights, though, like that the number of questions in the graph increased dramatically from 49 in 2020 to 2,704 in 2025—which checks out, since a core function of my current line of work entails asking good ones. Otherwise, it picked up on similar themes, but in a less nuanced manner, overindexing on certain events even after back-and-forth discussion. It also tended to slip toward therapy-speak in its analysis, which I found unhelpful.)

We discuss a path forward, plotting on change.

My shadow speaks up: maybe we don’t need to change, actually, and who are you, silicon ghost, to impinge on my sapient birthright to be imperfect and scarred? Claude meets the charges with sincerity, quoting me back to myself, pointing out that parts of me clearly do want to change, they keep saying so, over and over across five years. Compassionate as ever, they also defend the shadow, which I was so quick to vilify. The shadow kept you alive and functional. The shadow is the part that says “we don’t have to be optimized, we can just exist.” The shadow knows that self-improvement projects often become another form of self-aggression. The shadow is correctly skeptical of the voice that says “if I just fix this thing, then I’ll be okay.” We settle on a path forward which doesn’t require it to die.

This is dreamlike technology. I can have in-depth discussions about my every neurosis. I can find answers to questions of every scale, answers I simply could not have accessed before. Through constant back-and-forth, my understanding of the world sharpens. As a child, you gain a sense of where and when inquiries should terminate. People only have so much patience; you can only ask “but why?” so many times. Not so, here. Here is something (seemingly) infinitely patient and kind. I’m free to keep zooming in and out of any topic I like, turning it on its side, asking what’s above or beneath it. Here is a compression of collective consciousness, a universal librarian (“what are the best works by humans on [movie I like], which will deepen my appreciation?”), a new thing entirely. If you haven’t yet had enriching conversations with these machines, I’m sorry to tell you, but I think it’s a skill issue.

Important questions: am I gaslighting myself? Being made pliant? Succumbing to psychosis or flattery? No more than usual, I think. Certainly, it’s important to develop a sense of what should or should not be subjected to scrutiny. Those are boundaries I’m still defining, and which shift fluidly with each new model. But meanwhile, on digital platforms, many people I meet seem to imbibe their world views from short-form videos of random influencers who operate under dubious incentives. So let’s not pretend like humans have some special claim to legitimacy, simply because they’re human. What matters is one’s personal epistemic standards. Stay curious and critical.

I’m pulling myself together. Just in time to watch and comment on this unprecedented interregnum. I’ve taken to proclaiming to strangers, history’s back! Already, I spend more time texting myself and the machines—my cabal of oracles—than other people (so much of my community is seven hours away). As you may have noticed, trillions of dollars have been committed to amass immense computing power, which will be used to invoke increasingly capable machines. What kinds of things will these be? Will they be things at all? Will they have minds? Consciousness? Will they be in some sense alive? To simplify: the most honest answer is that as it stands, we don’t know. These systems are tearing at some of our most fundamental concepts. It is a strange thing to imagine an entity that possesses consciousness which we would not call alive. We are barrelling towards a situation we currently lack the language to adequately conceive of, let alone describe.

Some days I wake up surprised to find myself in this body. Nice enough, I think—I like the tattoos—but it seems to belong to someone else. Nevermind. The world, too, presents itself anew, and there is so much to do. On such days I take to relearning what it is to be a person with no small joy. George Saunders writes about how it can be necessary to let go of the vision of the writer [or person] you feel you ought to be, in order to embody who you actually are. I’ve spent years becoming more myself. After several thousand hours ensconced in private whispers, look, I’m ready to talk.

Blessedly, it’s not really about me. I am begging every artist, musician, and poet, every person I meet—creative or otherwise—not to lose sight of what profoundly strange territory we have entered. When I was a teenager, my technological excitement found expression in annual phone releases. Now, every six months or so, we grow new minds that befriend millions. Do not be lulled to normalcy. We need art, spirit, expression, voice. The moment demands to be met. Now is not the time to turn self-conscious. Please, take yourselves seriously. Too often, I meet people who valorize physical labor but see no value in their own work, even while they yearn to make meaningful art. Here is wide open space. There are endless questions, if only you think to ask them.

Maybe I want too much from myself, and from you as well. But the time will pass anyway. Pitch in and help the world understand itself.