My impossible search for the best, most powerful, most private journaling app ever

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An iPad, running Day One, on a wood desk.
Day One is a great app. It also asks you to trust it in a big way. | Image: Day One
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I have written in my journal 86 days in a row. It was my New Year’s resolution to actually commit to keeping a diary of my days, and every day since January 2nd, I’ve sat down and done so. This is the longest I’ve ever kept a journal — and almost certainly the longest I’ve ever stuck to a resolution of any kind. I’m probably more proud of myself than I should be.

I’ve been using the Day One app, which is the giant of the digital journal space. Day One works on practically every platform, is fast and simple, and lets me write text as well as save photos, audio, and links into my journal. It’s a great app!

But I had this moment, about a month into pouring my heart and soul (and hundreds of pictures of my newborn son) into Day One, where I started to worry about it. This app is a repository of my most private thoughts; I’ve also given it access to my location history, my calendar, and my camera roll. All of that information is beautifully organized, collated, and deeply problematic in the wrong hands. It’s also synced to the cloud, which means it’s stored on a bunch of mysterious machines other people control who knows where. Everything that makes Day One a great record of my life also makes it feel risky. Lots of people trust Day One, and I’ve trusted it every day for 86 days in a row. But should I? How do I know?

You can also hear a version of this story on this week’s episode of The Vergecast.

This isn’t just a question about journaling apps, either. As more of life moves online, we’re being asked to give more and more of our time, attention, and information to digital services. In return, we get a wealth of convenience: access to our stuff from anywhere, tools for organizing and using that stuff, easy collaboration with friends and family and co-workers. But almost all of these apps require access: to your data, your activity, your interests. Historically speaking, the apps that ask for your most sensitive data tend to also have the worst privacy records.

In this digital world, are there any spaces left that are just mine? Can I have all of those modern conveniences without constantly being asked to share, to socialize, to upgrade to the enterprise plan? I started out trying to figure out if I could trust my journaling app but wound up looking for a place of my own on the internet.