On the Temptation to Turn Your Journals Into a Bot
A reflection on whether turning 25 years of handwritten journals into a personal AI bot is a path to wisdom or just another distraction from being here now.
I’ve been keeping a journal of one kind or another since my mom suggested I might enjoy journaling. I was ten, standing at the sink next to her, helping with the dishes, when she put this idea into my little Universe.
Not one to waste any time, I walked downtown later that day with quarters from my piggy bank jingling in my pocket and bought my first journal at the Five and Dime store on Main Street: a small, faux-leather covered book with lined paper and gold rimming the edges of each page. It even came with a tiny lock and two tinier keys.
I still have that journal, along with dozens of others I’ve kept over the years, in a trunk in my attic.
The other day, I came across a thread on LinkedIn that caught my attention.
A thoughtful poster described how they’ve journaled daily for 25 years, filling Moleskins and collecting memories, observations, and stories. You know, the usual material of a life thoughtfully lived.
But here’s where it got interesting:
Over the past few months, this person has been reading their journals aloud into an AI platform. Not just to digitize them for posterity (like the way people scan old photos), but to lay the groundwork for something much more intimate and, frankly, eerie:
What if I turned all those journals into my own personal bot — one that knows my values, my preferred tone, my inner voices — and used it as a way to think through problems more objectively?
Another commenter chimed in, saying they had already done it. They uploaded 25 years of journals and were now conversing with a language model that, thanks to training on their most personal writing, could recall their memories faster than they could. Even more disconcerting, this personal GPT sometimes hallucinated, but did so convincingly enough that they didn’t catch it at first.
When I read this, my first reaction was simple:
No. Absolutely not.
Why?
Because I am not the me I was 25 years ago. And I’m certainly not the me I was at ten when I first started recording my thoughts and observations.
Sure, traces of that person linger. I like to believe we carry elements of ourselves throughout out lives no matter how many candles show up on our birthday cakes. But that Mary Lou is not this Mary Lou.
All that lived experience has put me where I am today.
How could something I wrote at 10 or 25 or 30 help me now?
I’ve already metabolized those insights or left them behind.
Memory fades for a reason.
But then…
The question sat with me.
What if it could help?
What if AI really is the through-line that could resurface insights I’ve forgotten, patterns I never noticed, lessons I didn’t fully absorb?
Is this a new tool for deeper self-discovery? Or just another seductive distraction dressed up as “personal growth”?
I think the deeper issue here isn’t whether or not to upload journals into an AI.
The real question is: What do we want from ourselves?
Do we want to live forward, trusting that who we are today is enough to navigate what’s ahead?
Or do we want to turn ourselves into archives to be endlessly mined for wisdom, as if our past self knows better than our present one?
AI intensifies this dilemma because it offers the illusion of objective feedback.
It promises to show you patterns, track your thoughts, help you think through your “skills gaps,” guide you to react “better.”
But it’s still a mirror.
A very sophisticated mirror, yes, but a mirror nonetheless.
And mirrors don’t mentor.
Mentorship is a human act: it requires being alive in the present moment, interpreting, questioning, feeling.
Even if the mentor is yourself, you are mentoring from who you are today, not some aggregate of past reflections.
I’m not saying this technology has no use.
If you’ve been with me for a while, you know I am not anti-tech, nor am I anti-progress. I use AI every day. I have a lifetime subscription to “Everything Changes.”
Maybe there’s value in revisiting what we’ve written, letting AI surface forgotten ideas.
But I can’t get beyond the idea that this will never substitute for being present to ourselves in the messy, evolving, imperfect ways we experience life.
There’s no hack for that.
So no, I won’t be uploading my journals to a bot anytime soon.
Not because I’m afraid of what it might show me, but because I trust myself — this self, here, now — to decide what matters.
And maybe that’s the most important skill we’re being asked to cultivate and remember right now:
How to be present to our lives without mediation.
How to trust that what we’ve already integrated is enough.
How to let go of needing perfect recall, and to get on with living.
Would you upload your journals into a bot?
Do you think it would help, or just turn memory into another digital commodity?
I’m curious what you think.