The unnecessary tweak to the keyword in the title refers to Cory Doctorow’s term, which describes the systematic, gradual decline in the quality and user experience of online platforms and digital services. My variation is unnecessary because it doesn’t enhance the meaning beyond centring the reason for this decline: AI. But I have included it for emphasis.

Up until recently, Day One had resisted enshittification, although its purchase by Automattic, the owners of the now-bloated WordPress and Jetpack, should have signalled this was coming.

I’ve used Day One for more than a decade. It was an excellent journalling app. Private, minimal, easy to use, with excellent features such as geolocation, weather, ‘On this Day’, and book printing. Features that got out of the way and either worked quietly in the background or appeared only when you summoned them. That’s changed.

Now there are new subscription tiers. Previously, the tiers were Free and Premium. Simple. Premium included sync and a few other things that I can’t remember, but it was compelling enough that I’ve been a Premium subscriber from the beginning. Now, without consultation, I’m Silver (not Premium), and there’s a new, more expensive AI-driven tier, Gold. I don’t object solely on that basis. You would think I could just choose to remain on ‘Silver’ and all would be well. But no. Even with these features turned off in settings, I’m visually prompted in the app to upgrade to Gold and use the Daily Chat (with AI), which I’ve turned off and can only use if I upgrade. And yet, there it is, taunting me.

It’s infuriating, even if it’s the way most things are heading. This is not about being sanctimonious or anti-AI; I would consider looking the other way if I could. I want the choice.

I’m exporting and exploring alternatives. For day-to-day journaling, I will likely land in Bear.

The features I will most miss are On This Day and book printing. I can replicate On This Day with shortcuts and widgets. I’ve also been using Flohgro’s excellent On This Day Rewind App. Book printing, which I use to curate personal memories for my kids, will be a bigger pain point and harder to replace. My research hasn’t turned up much. I’ve looked at Blurb, Momento and others. None fully replicate what Day One does natively.

As an aside: why is book printing still so painful in 2026?