Back in 1998 I started writing online, before “blogging” was even a thing. At the time, it was just ‘online journaling’ – me recording my thoughts and experiences so I wouldn’t have to keep retelling the same tired old stories. Over the years it became a kind of lifelong project: now with 1,600 posts (that take up 2,800 pages in a Word document!!!) spanning relationships, career reinventions, family struggles, travels, ideas, failures, and a few occasional rants.
Today I did something that would’ve sounded like science fiction a few years ago: I uploaded my entire archive of blog posts into AI.
What does that even mean? It means every post I’ve written since 1998 is now in its memory when it works with me. It can see the whole arc of my life as I’ve described it. It can track my cycles of excitement and burnout, the repeating patterns I’ve had in relationships, the ways I’ve chased reinvention, and the shifts in how I’ve seen myself over the years.
It has the big picture view of my life, in a way I could never have.
To be honest, it’s pretty damn exciting. Having an AI reflect back what I’ve written over 30 years highlights what I’ve struggled to learn, where I’ve kept tripping over the same issues, and also where I’ve quietly grown. I can see that it can help out with a kind of therapy.
It also raises a bigger question: what happens when an AI knows your voice, your patterns, your history – better than anyone else does? What can it teach you about yourself that you’ve been too close to see?
I’ve already been exploring what that might look like, and I’m amazed at what I’ve already learned about myself just this afternoon from what it’s been able to tell me.
For me, this is about exploring what’s possible when technology doesn’t just give you information, but actually helps you see yourself more clearly.
I don’t really know yet what I’ll do with this experiment. I’ve already started exploring the things I’ve seen as weaknesses and how they can actually be strengths leading me into bigger and better things in my future.
Maybe it can also help me connect some of my threads into a book. Maybe it’ll simply help me stop repeating old mistakes. Or maybe it can just give me a clearer view of where I’ve been, so I can walk more consciously into whatever comes next.
Either way, after almost 30 years of writing my story, it feels strangely fitting that the next chapter is being co-written with an AI that now knows it as well as I do.
At a deeper level, it makes me wonder if this is the start of something bigger – if our stories, captured and reflected back by machines, might one day become part of how we evolve. What does it mean to be known by an intelligence that has no judgement, only memory and reflection? What happens when we can explore our lives not just through hindsight, but through a kind of dialogue with the past and future at once?
Maybe that’s the real experiment here: not just how AI can help me write better, or live better, but how it can help me see myself differently. And maybe that’s the beginning of a new kind of journey – one I couldn’t have imagined when I started writing all those years ago.
And so the journey continues.
But I’m curious about you – if you could feed your own history into something like this, would you? And what would you hope it might show you?
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