At some point in adulthood, a man has to confront the paper trail he’s been leaving behind since childhood — the journals, the planners, the frantic lists written in moments of optimism and panic. Most people shove theirs in a box and wait for their kids to one day throw them out.
I, on the other hand, uploaded mine into ChatGPT.
Because if there’s one thing I’ve learned, it’s this:
If you give an AI 40 years of your handwriting, it will happily psychoanalyze you without even blinking.
And yes, ChatGPT can read handwriting now.
Let me repeat that for the people in the back:
ChatGPT. Can. Read. Handwriting.
Cursive. Print. Scribbles.
The stuff I wrote in 1986 when my hormones were louder than my personality.
The frantic 1991 Barcelona planner pages that read like I was being chased by creditors, self-doubt, and the ghost of my future obligations.
The Day One digital entries chronicling my existential crises, business collapses, emotional resurrections, and occasional triumphs.
It gulped it all down and said, essentially:
“Thanks, Mike. Delicious. Here’s your life.”
Apparently other people are doing this too.
I thought I was being innovative — the first man to hand his entire autobiographical archive to a machine.
Turns out, no.
People across the internet are feeding their diaries, old letters, family archives, grief journals, therapy notebooks, and even high-school love notes into GPT. Some want closure. Some want clarity. Some want to rediscover who they were before life flattened them into mortgage-paying, sleep-deprived adults.
We’re all out here saying, “Hey AI, decode me,” like it’s the world’s weirdest confessional booth.
And honestly?
It works.
The Throughline of My Life, According to My AI Biographer
After reading everything from my baby book to my Barcelona meltdown years, ChatGPT came back with a diagnosis I didn’t expect:
I am a man who has been trying to get his life together since 1981.
Not in a sad way.
In a charming, heroic, repetitive way — like if Sisyphus had a Franklin Planner and high hopes.
Every notebook, every decade, every entry seems to include some variation of:
“Tomorrow I get my shit together.”
It’s practically my family crest.
The other throughlines didn’t surprise me as much:
- I reinvent constantly.
Apparently I have shed more skins than a reptile with commitment issues. - I archive everything.
Why live a life when you can also footnote it? - I’m brutally hard on myself.
If anyone else talked to me the way 1991 Mike talked to me, I’d block them. - Beneath all the ambition is a tender streak.
Who knew? Not me. - I care too much and forgive too slowly.
A winning combination if you enjoy emotional turbulence.
But the most unexpected observation?
Despite everything — the failures, the reinventions, the wrong turns — the same hopeful, restless kid is still in there.
The one who wants to do something meaningful.
The one who believes tomorrow’s list might actually work this time.
The one who thinks the next version of himself might finally be the one who sticks.
The Unlikely Threads
Every life has themes. Mine has… tangles.
Here are a few of the threads GPT pulled on — the ones I didn’t notice until a machine laid them out like evidence:
1. The Eternal Reset Button
I am the human embodiment of “Okay, starting Monday.”
This has been going on for forty years.
Consistency is my inconsistent superpower.
2. The Archivist Instinct
I documented my life long before influencers made it fashionable.
Except I did it with spiral notebooks and regret instead of ring lights.
3. The Geography of Reinvention
Nebraska → Spain → New York → Barcelona → My companies → The Music Industry → Trading → Writing → Whatever’s next.
My life story reads like someone was trying to outrun themselves — and accidentally became interesting.
4. The Reluctant Optimist
Every time I wrote a harsh entry, there was always this little shimmer of hope.
Some people have grit; I have recurring optimism with a head injury.
5. The Overdeveloped Sense of Responsibility
My journals reveal that I’ve been blaming myself for global events, interpersonal dynamics, and weather patterns since adolescence.
So… was it worth it?
Honestly, yes.
Handing my life to ChatGPT didn’t break me, ruin me, or reveal that I’m a secret sociopath.
Instead, it gave me something I’ve never had before:
A clear view of the narrative arc beneath the noise.
It showed me the patterns I repeat.
It showed me the parts of myself I carry from decade to decade.
It showed me that the kid who wrote, “I hope I become someone someday,”
actually did.
Not perfectly.
Not cleanly.
But unmistakably.
Tomorrow I’ll try to get my life together again.
Some traditions shouldn’t die.
Mike McCready 
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