In 2018, I sat in a Starbucks on North State Street in Chicago and realized I was a total fraud. I had this $30 Moleskine notebook, the thick kind with the heavy paper that makes you feel like Hemingway, and I left it on the condiment stand next to the half-and-half. By the time I walked back three minutes later, it was gone. I didn’t care about the notebook. I cared that I’d lost six months of “deep thoughts” that, if I’m honest, were mostly just grocery lists and half-baked complaints about my boss at the time. I felt naked. But more than that, I felt stupid for trying to be a “paper person” when I live my entire life on a glass rectangle.
Since that day, I’ve been on a crusade to find the best journal app for iPhone. I’m not a tech reviewer. I work a regular job in operations. But I have spent exactly $412.80 on journaling subscriptions and “pro” unlocks over the last six years. I’ve tracked my entry consistency across 11 different apps. I’ve even exported my data into spreadsheets to see which UI made me write more. (The answer: it’s never the one you think.)
The Day One dilemma and why I’m bitter
Look, we have to talk about Day One. It’s the one everyone recommends. It’s beautiful. It’s polished. It has that satisfying “click” sound when you check a box. But I’m going to say something that might be wrong, or at least unpopular: Day One has become a bloated mess of rent-seeking features.
I used to love it. Then they moved to the subscription model, and suddenly I’m paying $35 a year to look at my own memories? It feels like a high-maintenance garden where the gardener charges you every time you want to walk through the gate. What I mean is—actually, let me put it differently. It’s a great app, but it’s trying too hard to be your entire life. Audio entries, photo books, Instagram integration… it’s too much. I found that the more features they added, the less I actually wrote. I spent more time “organizing” my journals than actually reflecting on my day.
The best journal app is the one that doesn’t make you feel like you’re performing for an audience of one.
I still have 1,402 entries in Day One. I haven’t deleted them. But I haven’t opened the app in four months. I’m tired of being upsold on “premium” features just to write down that I had a mediocre taco for lunch. It’s a digital graveyard.
Apple’s Journal app is creepy, and I love it
When Apple announced their own Journal app, I was ready to hate it. I figured it would be a bare-bones Notes app clone. I was wrong. It’s actually the only thing that has kept me journaling daily for the last 180 days.
Here’s the thing: I’m lazy. Most people are. Apple Journal uses “Suggestions,” which is basically a private investigator that lives in your pocket. It knows where you went (GPS), who you texted (Contacts), and what music you listened to. It’ll ping me and say, “You spent the afternoon at Griffith Park, want to write about it?”
I know people will disagree, but I don’t care about the privacy implications as much as I care about the friction. Apple claims it’s all on-device encryption, and I choose to believe them because the alternative is too exhausting to worry about. I’ve found that my average entry length on the Apple Journal app is 142 words, compared to just 55 words when I was using a blank prompt in other apps. The prompts actually work.
It’s not perfect. You can’t use it on a Mac (which is insane), and you can’t search your entries yet. But for a free app that comes on your phone? It’s hard to beat. It’s just… easy.
The Obsidian trap (or: why I hate the nerds)
If you go on Reddit or YouTube, people will tell you to use Obsidian. They’ll talk about “Personal Knowledge Management” and “Zettelkasten” and “linking your thoughts.”
I tried it for three weeks. It was the most unproductive twenty-one days of my life. I spent six hours watching tutorials on how to set up a “daily note template” and zero minutes actually writing about my feelings. Obsidian is for people who want to feel like they’re building a second brain because their first one is too busy worrying about plugins.
I might be wrong about this, but I think journaling should be messy. It shouldn’t require a Markdown syntax guide. If I have to use brackets to link to my “Mood Tracker” page, I’m not journaling; I’m coding. I actively tell my friends to avoid Obsidian unless they are literally a research scientist. For a regular person who just wants to vent about their mother-in-law? Total waste of time.
The part nobody talks about
I did a little experiment last year. I tracked my entry length for three months. I found that when I journaled on my Mac, my entries were roughly 600 words of absolute garbage. When I wrote on my iPhone, they were shorter, punchier, and much more honest.
There’s something about the thumb-typing that forces you to get to the point. You don’t have the luxury of rambling when your thumbs are getting tired. This is why I think the “best” app has to be mobile-first.
- Daylio: Great if you hate writing and just want to tap icons. I used it for 2 years. It’s good for data, bad for soul-searching.
- Notes App: Honestly? Underrated. I have a folder called “Vents” where I just write stuff I’m going to delete later. No pressure.
- Reflectly: Too much “AI” coaching. I don’t need a robot to ask me how my day was with a smiley face icon. It feels patronizing.
Anyway, I’m rambling. But I digress.
The verdict
If you want the absolute best experience and you don’t mind the “subscription tax,” go with Day One. It’s the industry leader for a reason, even if I find it annoying.
But if you’re like me—a bit cynical, a bit lazy, and tired of everything being a “system”—just use the Apple Journal app. It’s already there. It’s free. It’s creepy in a way that actually helps you remember your life.
I still think about that Moleskine in Chicago sometimes. I wonder if someone read it. I wonder if they thought my grocery lists were profound. Probably not. That’s the thing about journaling—it’s only for you. The app is just the bucket you catch the rain in. Don’t spend too much time picking out the bucket.
Just start writing. That’s the whole trick.
Does anyone actually go back and read their old journals? I realized the other day that I haven’t looked at an entry from 2021 once. Maybe the whole point isn’t the record, but the release. I honestly don’t know.
