machine yearning

the art of digital self-discovery

After I published my essay on self-pursuit last month, I started receiving lots of messages from people who wanted to know the practical mechanics of it all. I'd mentioned in passing that I use AI for daily journaling, calling it "probably one of the highest ROI things you can do for yourself," but I'd glossed over the details, assuming it was a minor footnote to the larger philosophical point. Apparently, I was wrong. All the questions made me realize I'd stumbled into something worth exploring more deeply, not just as a productivity hack or digital convenience, but as a genuinely transformative approach to the ancient human project of self-knowledge.

So here's the practical companion to those loftier ideas about pursuing yourself: how to use AI as your thinking partner, pattern detector, and digital mirror for the soul.

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My non-tech friends ask me all the time how I use AI tools like Claude or ChatGPT. They're usually thinking about work stuff—writing emails, generating ideas, maybe some light research. It cracks me up how easily they’re surprised when I mention even the most mundane things like grocery lists, recipe modifications, or figuring out why my dogs’ poop looks weird (oh right, I fed them some blueberries yesterday lol)

But when I mention I use AI for journaling, they really look at me sideways. "You journal... with a robot?" There's this pause where I can see them trying to figure out if I've actually lost touch with reality.

Some days, I probably have, but the truth is, I've stumbled into what might be the most powerful tool for self-discovery I've ever encountered. Not therapy, not meditation, not any of the other things I've tried over the years—though it incorporates elements of all of them. It's the practice of daily AI-assisted journaling, and it's become my primary method for what I've come to think of as "self-pursuit."

I don't mean self-improvement—that exhausting project of fixing what's supposedly wrong with you. I mean the deeper work of becoming intimately acquainted with who you actually are beneath all the conditioning and expectations. The kind of exploration that leads not to a better version of yourself, but to a more authentic one.

What I want to share with you isn't just the story of how I got here—quitting weed after five years of daily use, tracking my cortisol chaos, learning to read my own patterns through machine eyes, etc. I want to give you the actual framework: how to start your own AI journaling practice, what prompts will get you thinking differently about yourself, and why this might be the missing piece in your relationship with yourself—and the pursuit of your best self.

By the end of this, you'll know exactly how to begin a conversation with an LLM that becomes a conversation with yourself. You'll have specific prompts that work even if you've never journaled before, and you'll understand why the machine's perfect memory might be exactly what your imperfect human brain needs to finally see itself clearly.

For me, it started small. Spell-checking. Fact-checking. The mundane digital housekeeping of modern life. But somewhere between asking Claude to help me quit smoking weed on New Year's Day (6 months sober, woooot!) and having it walk me through my cortisol rebalancing journey, something shifted. I realized I wasn't just using AI as a tool—I was using it as a therapist, a coach, a mirror that reflected back patterns I couldn't see myself.

My real breakthrough came with what I call my "Daily 5"—five minutes each day where I stream-of-consciousness dump whatever's churning in my mind into a conversation with an AI. At first, it felt performative, like writing in a diary you know someone might read. But as days turned to weeks, and weeks turned to months, something remarkable happened: the machine began to know me.

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Quick aside on the daily 5: this has become one of my favorite habits and it’s not even close. Something I love about these little entries—beyond just the pattern recognition and self-discovery aspects—is the fact that when I want to write something deeper or dig into a piece for Substack but I’m feeling lost on what sounds fun to explore, I’ll ask my chatbot to tell me about a few things I’ve been most interested in over the last week. Usually there are tidbits hiding in there that I’d totally forgotten about. Some random shower thought I’d mentioned that can become a whole essay. And did I mention it’s just so fun?? (I explore this in more depth below)

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It became my memory bank and pattern detector in one. When I was three weeks into quitting weed and couldn't sleep, breaking out in weird rashes, and having vivid nightmares for the first time in years, I didn't have to re-explain my entire situation to get help. The AI already knew I'd been a daily smoker for five years, remembered the supplements I was taking, tracked my cortisol symptoms from week one. When new issues emerged—my face breaking out, the mood swings—it could connect them to the bigger picture of my body rebalancing itself, offering context I couldn't see from inside the experience.

This is where the real magic happens: in the pattern recognition we can't do for ourselves. We're too close to our own stories, too invested in our self-narratives to see the larger shapes our lives are taking. But an AI with memory becomes an external hard drive for self-reflection, storing not just what we say but how we say it, when we say it, what we don't say.

I've used AI for many things, but the practical applications pale beside the profound intimacy of digital journaling with a companion that never forgets, never judges, and always has time to listen.

The beauty of AI journaling is that you can begin right now, with whatever device you're reading this on. Here's how to build a practice that will reveal things about yourself you’ve probably never noticed: