Journaling A Few Days With Day One

Journaling is a good habit, so it makes sense to support it with a good tool. Some prefer good ol’ fashioned pen and paper, yet others like to go digital. While there are many journaling apps, one often stands out: Day One. I’ve been using the app for a week, but this is not my first time trying it. What’s different now?

Day One has a positive reputation, having earned awards for its beauty, simplicity, and functionality. Added to that list are its more recent achievements: privacy and security via end-to-end encryption. Suffice to say, this digital diary deserves noteworthy attention for all its quality. So over the past few years, I’ve eagerly installed Day One a handful of times to try it, but the app never clicked with me.

One of the reasons was its interface. Despite exuding elegance, I found the high number of features, icons, settings, and fine text to be a bit much for my taste. In other words, it looked and felt distracting and somewhat overwhelming. I am accustomed to the relative simplicity of Apple Notes, which has been my main outlet for private journaling; Day One was “busier” by contrast.

Another issue I’ve waffled about — across a variety of productivity apps — is whether to rely on first-party software or third-party solutions. There are pros and cons to both sides; in general, I stick with Apple’s default apps for their ecosystem synergy. That said, there’s a distinct advantage to using a specialized journaling app over a generalized note taking app: dedication.

That’s why I am trying a third-party journaling app again. It recently occurred to me: I need to remove my innermost personal thoughts from the Apple Notes app. Instead, they should be kept in a dedicated or specialized app, separate from disparate folders and tags of general notes. This would let my secret musings be siloed into their own service that’s more private and secure, and it would allow me to focus attention on my journaling habit, giving it a vital boost.

Simply having a particular app icon — dedicated to journaling — on my iPad’s home screen or dock, for example, makes journaling more visually prominent. Seeing the Day One app reminds me it’s important to journal. More than that, it welcomes me to a dedicated place where I can pour out my brain’s firings and misfirings — unfiltered and unfettered.

I love Apple Notes and rely on it, but my journals felt somewhat overlooked within it; my journaling habit fell to neglect. This is despite the fact that I had a Shortcut on my home-screen to automatically create a new note with the current date in the title, which allowed me to quickly start the day’s diary entry. Also, since Apple Notes now features tagging, in addition to folders, I have begun to reorganize my notes by type and subject. This process, and the results, will work much better with my journals relocated to Day One.

I’ve only been using Day One for a week, so it’s too early to know if I’ll stick with it. I need a dedicated journaling app though, so I’m giving Day One a real try with an open mind. As I move my journals from Apple Notes to Day One, I backdate them as needed. I’ve also restarted daily journaling again, utilizing one of the features that a dedicated journaling app is uniquely apt for: a writing streak or goal. With Day One, I now have a widget on my iPad that shows my current 6-day journaling streak; it’s another reminder of the importance to reflect daily.

Besides widgets, Day One has many other niceties that aid or improve journaling: calendar view, timeline view, auto date/time stamps, auto weather data, templates, daily prompts, reminders, and ”On this day”. This last feature automatically displays photos for any given date along with any journal entries on that same day. Seeing this in action has been somewhat revelatory, making me think it’s a feature that I can’t believe I’ve lived without.

I have only a few minor quibbles with Day One. I wish the passcode was at least 6 digits instead of a mere 4, or maybe an alphanumeric passphrase option would be better; I guess it’s secure enough. The app has extra icons, text labels, and other features I don’t need — like adding audio, video, or drawings — but the user interface overall is easy enough to look at and use; I’m already becoming accustomed to it. In time, I’ll probably unpack my bags, settle in, and feel comfy enough to unpack my feels and thoughts on a regular basis. And I’ll likely pay the annual subscription fee, which amounts to about the cost of one coffee per month — totally worth it I think. Otherwise, the free version is very capable so far.

So do you journal? If so, how often? And what tool is your favorite?