Twenty Years of Notebooks, Nine Uncomfortable Discoveries

A reader named Marcy wrote to me last spring with a question I haven't been able to shake: *"I have fourteen years of journals in a shoebox. Is it worth opening? Or should I just let them be?"

I told her I'd find out myself before answering. So one rainy Saturday in March, I hauled every notebook I own onto the dining room table — a stack that started in a freshman dorm in 2004 and ends, embarrassingly, with a grocery list from last Tuesday that I mistook for a journal. Twenty years. Forty-one notebooks. One pot of coffee that went cold because I forgot it existed.

Marcy, this one's for you. Here's what's in the boxes.

1. Almost none of my worries came true

I kept a running tally as I read, because I'm that kind of person: of the roughly two hundred specific disasters I predicted in these pages — failed careers, friendships ending over nothing, money running out, a mysterious lump that turned out to be a mosquito bite I scratched into a scar — exactly three happened. And the three that happened? I never once saw them coming. Not a single page of dread was spent on the things that actually broke my heart.

Worry, it turns out, is a very confident forecaster with a terrible record. If you take one thing from this letter, take that.

2. I had the same good idea four times and abandoned it every time

In 2007, 2011, 2015, and 2019 — almost eerily on schedule — I wrote some version of: "What if I wrote letters to strangers and published them?" Four separate eras of me had the same idea, got excited, and let it die of natural causes within a week.

If you're reading this website, you know how that story ends. The idea wasn't bad. It was just early, every single time, waiting for me to catch up to it. Some dreams don't die. They hibernate.

3. My handwriting got worse exactly when my life got better

There's a stretch of 2013 where the script deteriorates into what I can only describe as a spider's farewell note. I remember that year. It was a good one. I was too busy living to be legible. The neat, careful journals — the ones with washi tape and margin drawings? Those were the hard years, when I had time to decorate my sadness.

4. I was in love with being a writer before I wrote anything

The early notebooks are 80% descriptions of the life I would have once I was a writer — the cabin, the mug, the dog named after a Faulkner character — and 20% actual sentences. It took me years to flip that ratio. If young Ali could see this desk, she'd be thrilled about the words and mildly disappointed about the dog. (His name is Biscuit. He's fine.)

5. The people I wrote about angriest are the ones I miss most

This is the uncomfortable one Marcy warned me about, or would have, if she'd known. The journals from my late twenties contain some genuinely vicious passages about two people — one a former roommate, one a former boss. Rereading them, I mostly felt embarrassed by my own certainty. And underneath the embarrassment, a quieter thing: I missed them both. Anger, in my notebooks at least, was just grief wearing a costume.

6. Gratitude entries were always the shortest

Every time I tried a gratitude practice, the entries lasted about four days and three sentences. But the complaint entries? Novellas. I don't think that makes me ungrateful. I think it means bad days need processing and good days just need living. Still — I'd like more of those three-sentence entries going forward.

7. The best advice in twenty years of journals came from my mother, secondhand

Buried in a 2009 entry, quoted without attribution because apparently I forgot whose it was: "You don't have to finish it. You just have to not quit while it's still yours." I had to sit with that one for a while. I'd been carrying it around for fifteen years without remembering where I got it. Sorry, Mom. Credit restored.

8. I solved problems by writing about anything but the problem

Page after page, I'd spend two thousand words describing a neighbor's fence, a recipe, a bird at the feeder — and then, in the last line, casually resolve the actual crisis I'd been avoiding. The journals were never about what they were about. Writing, I kept proving to myself, is how I sneak up on the truth.

9. The person in the pages deserved more kindness than I gave her

Reading myself at 24, panicking about being behind at an age I'd now trade a vacation to revisit — I wanted to reach through the paper and say, you're doing better than you think, and the worrying (see item 1) is optional. I couldn't. But I could write this, for whoever is currently 24 in their own shoebox of notebooks: future you is not disappointed. Future you is fond of you. Almost annoyingly so.

So, Marcy: open the box

I wrote back to her last week. Here's the short version of what I said: the journals won't be what you fear and won't be what you hope. They'll be something better — a letter from someone who knew you first, and loved you anyway, in handwriting only you can read.

And if you do open them, do what I did: keep a fresh notebook beside you. Twenty years of evidence says the next good idea is already in there, waiting for its fourth or fifth chance.