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Keeping a Journal With Day One


Keeping a journal is great for your mental health. It can help to increase self-esteem, relieve stress, boost creativity and help you better understand your own feelings. The one issue most people encounter with journaling is turning it from an occasional thing, into a regular habit.

Although there’s a lot to be said for using a paper journal, they’re ridiculously inconvenient. You have to keep track of it, and make sure to have it with you when you want to journal. While it’s not impossible to do, it is one more barrier that makes it harder for you to keep a journal. Instead, you want your journaling experience to be frictionless.

One of the best solutions is a Mac and iOS app called Day One. It provides a beautiful cross platform experience that makes keeping a journal as simple as possible. In this tutorial, I’ll show you how to start journalling with Day One.

Introducing Day One

Day One is billed as “a simple and elegant journal for iPhone, iPad and Mac”—something it delivers on. It’s racked up multiple awards from Apple and other sources for the app’s design. Day One takes a minimalist, but functional approach that fits well with iOS 9 and OS X El Capitan.

The timeline in Day One.

While you can just use Day One on a single platform, you’ll get a better journaling experience if you have it on all your devices. You can download the OS X version from the Mac App Store for $9.99 and the iOS version from the iOS App Store for $4.99.

Writing a Journal Entry

The Day One experience is consistent across all platforms. To start a new journal entry click or tap on the Plus icon. On iOS, you can add a photo by tapping on the Camera icon.

ios app
Creating a new entry in the iOS app.

When you create a new entry, Day One will automatically pull in details about the location, the weather, what music you have playing and some other background information. You can configure this in Day One’s Preferences. You can also manually add tags or star specific journal entries.

Creating a new entry in the OS X app.

To format your Day One entries, use Markdown. It’s supported on both OS X and iOS. I’ve written an introduction to Markdown, that you may find helpful. Although journal entries don’t often require formatting, it is handy to occasionally be able to create bulleted lists, or emphasise certain words.

When you’re finished writing a journal entry, click Done.

Setting Up Reminders to Write

Even with the best will in the world, remembering to write in a journal is tough. Fortunately, Day One has a build in reminder function to prompt you to keep at it.

The Reminders preferences pane.

On iOS, head to the app’s Settings screen and select Reminders. There you can add reminders for you to write for any time you want. You can limit them only to certain days, so if you want a reminder to journal in the morning on weekdays you can have it without being woken early by a push notification on the weekends.

quick entry
The Quick Entry app.

On OS X, there’s a dedicated Reminders tab. For the Mac app, the reminder control is a bit more granular. You can set Day One to remind you every 15 minutes, hour, day, week, or anything in between. OS X reminders pop up in a dedicated, Quick Entry menu bar app. As soon as you’re prompted to, you can start writing without having to open the full app.

Syncing Entries Across Devices

The best thing about using a digital journal is that you can have it on every device you own. It’s as easy to journal while sitting on a train as when you’re alone in your home. If something happens and you want to write about it, you can just whip out your iPhone anywhere and start journalling. 

For this to work properly, Day One needs to be set up to sync across devices.

sync configuration
The Sync configuration screen.

Day One offers three options for syncing your journal: iCloud, Dropbox and Day One Sync. Both iCloud and Dropbox, however, are more legacy features. While Day One will continue to support them, the newer Day One sync is set to have a lot of extra features added. I’d recommend using it, but if privacy is important, it all comes down to whether you trust Apple, Dropbox, or Day One’s developers most with your data.

To set up sync, head to the Settings panel on the OS X or iOS app. Select Sync and choose the option you want to use. You’ll need an account with the relevant service. You can sign up for a Day One account here. Make sure to use the same service for both the OS X and iOS apps.

Coming Up With Ideas

One of the hardest things about journaling is coming up with ideas on what to write about. If your day was fairly routine and uneventful, it can be difficult to think of anything to say. 

At the start of every new entry Day One has a prompt like, “Who was your first date?” in case you’re stuck. I’ve found, however, that these aren’t particularly inspiring and repeat too often.

To fix that problem, I created my own TextExpander snippet to prompt me with journalling ideas. I’ve written a lot about TextExpander but I covered how to create that exact snippet in my tutorial on Fill Ins.

Securing A Day One Journal

A journal can, and should, be an incredibly private thing. You have to be comfortable writing down your most private thoughts knowing that they can’t be read by anyone who borrows your phone or Mac. With Day One you can password protect your journal, or if you have an iPhone with a TouchID sensor, fingerprint protect it.

To add a password to a Day One journal, open the Settings menu. On OS X, head to the Security tab and check Enable Password Protection. On iOS, turn the Password and TouchID switches on. You can configure how long a journal stays unlocked after you enter the password.


Keeping a journal is great for your mental health. While physical journals have their advantages, they can’t compare to using a Mac and iDevices. Day One is a great cross platform app that makes it really easy for you to keep a journal. In this tutorial I’ve looked at how to get started using it to do just that. While you could roll your on solution with an app like Apple’s Notes, Day One’s extra features make it a better solution.

If you’ve any questions about using Day One please let me know in the comments. I’ll be happy to help.

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