(2023-03-31) My Impossible Search For The Best Most Powerful Most Private Journaling App Ever

My impossible search for the best, most powerful, most private journaling app ever. I have written in my journal 86 days in a row

I’ve been using the Day One app, which is the giant of the digital journal space.

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.

Everything that makes Day One a great record of my life also makes it feel risky.

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.

Historically speaking, the apps that ask for your most sensitive data tend to also have the worst privacy records.

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.

instead of storing information in a central location and then building local apps that pinged that server, Mayne built Day One on top of the Mac’s file system. “By default, only whoever has access to your computer would see it,” Mayne says. “The downside being, if you lose that computer, you lose all those memories.”

Now, Day One syncs across a huge number of platforms: iOS, Android, Windows, Mac, and even, as of recently, the web. That’s a big part of the reason I use it.

Day One rolled out its own end-to-end encrypted syncing service, which it still uses now.

Encrypted sync comes at a cost, though. It’s hard for outside services to access encrypted data — that’s the whole point — which makes it hard to connect Day One to other apps.

There are a million examples of this tradeoff, but the simplest one is probably passwords

The note-taking app Obsidian, another Personal App I’ve come to like, tackles the problem a bit differently.

when you first install it, it’s really just a simple text editor on top of a folder of files on your device. But you can turn on a few “Core plug-ins” like multi-device sync or the ability to share a note publicly. And if you’re really inclined, you can enable and install third-party plug-ins

I’m generally not an online privacy zealot.

But I’ve become somewhat maniacal about ensuring the longevity of my stuff. Servers break; products pivot; companies get acquired or go out of business or kill their less-loved stuff. No app is forever

my journal entries and notes need to outlast Day One and Obsidian. That’s why every good Personal App also needs to have great export tools

There’s no perfect answer to this, and ultimately you just have to decide which compromises you can live with.

For most of my day-to-day life, I’m still in Google Docs and Gmail and the like — going Full Privacy is more work than it’s worth, at least for me, at least for now. But I’ve found that having a few trusted digital spaces has made my life better.

I use Day One for my daily journaling. I use Obsidian for all my projects and notes. I use 1Password to store not just my passwords but also my account numbers and personal documents.