Should You Upgrade to Day One 2?

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In recent years, folks with a story to tell have turned to Day One, the incredibly popular journaling app for OS X and iOS. Earlier this year, developers Bloom Built introduced Day One 2, which isn’t an upgrade, but rather a completely new application. The previous version now becomes Day One Classic.

So is Day One 2 worth buying all over again? Let’s find out.

Change Is in the Air

There are two big changes in Day One 2: the ability to add multiple journals (up to 10), and the addition of multiple photos per entry (again, as many as 10). To keep things organised, users can now pick from an array of colors to uniquely identify one journal from the other. In another change, users now have the ability to toggle between List, Photo, Map, and Calendar views. You can also sort and find entries quickly through the use of a star, tagging, years, and other filters.


Behind the scenes, Bloom Built has changed how journal entries are backed up and synced. Previously, Day One users had the choice of syncing data through Dropbox, iCloud, or the company’s proprietary service, Day One Sync.

In Day One 2, Day One Sync is the only supported sync service. Bloom Built cites “reliability and security” as the main reasons for discontinuing support for Dropbox and iCloud, stating that the other services “had too many cases of data loss and duplication.”

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Day One 2 also includes some minor feature upgrades, including 3D Touch support, custom reminders, and timezone support.

Multiple Journals

As a long-time Day One user, I never thought I needed multiple journals. The application’s tagging system was all I thought was necessary to organize my daily thoughts. I was wrong.


Having multiple journals, in different colors, has changed how I write. In Day One 2, I organize my thoughts primarily between two journals, Personal, and Work-Related. A third journal, Vacation, is helping me with planning a trip. The application uses this division throughout. For example, one can filter journals via the map or photo viewer.

Map View

Visualization is important when telling a story, and the new map screen takes that concept to a new level. Now you can see where you were when making a journal entry. This information proves useful over time as one adds entries.

For example, I tend to journal more when I’m working from Starbucks, rather than from my home office. As a writer, knowing this information is of great importance. It could be that I’m less distracted at Starbucks, which is great to know on days when I’m struggling to find the right words for a story.


Day One 2 on iOS also features a nice little feature called “View Visible Region in Timeline,” which gives you a summary of all entries written within the area on the map. A minor feature, of course, but a good one nonetheless.

All Those Images

In Day One Classic, you’re limited to one image per entry. Imagine being on a family vacation and only allowed to choose one image to represent the experience on any given day. In Day One 2, you can add up to 10 photos for each entry. That family vacation will look so much better now, dont you think?


Easy Syncing

One of the things that annoyed me most about Day One Classic was the intermittent appearance of duplicate entries, which occurred with both Dropbox and iCloud as my backup solution. It happened most when using Day One on a new device for the first time.

Duplication is no longer a problem in Day One 2, courtesy of Day One Sync. I’d like to note that my duplicate entries had already disappeared in 2015 when the service first arrived on Day One Classic.

What Hasn’t Changed?

Simplicity was one of the reasons Day One Classic found success. The application received nearly 40 free updates over the course of its product life cycle. Each of these updates enhanced the writing experience but did not change the way to add journal entries.

As we once noted about Day One, “Simple lines and simple fonts, yet great typography make Day One a pleasure on the eye.”


In Day One 2, this simplicity remains. Setting up Day One 2 is effortless, and beginning that first entry couldn’t be more intuitive.

Mac Versus iOS

When Day One 2 launched, I first purchased the iOS version. I waited for a few days before buying the Mac version. The reason for this hesitation was the price disparity between each version.


The iOS version of Day One 2 is $9.99. For a limited time, it’s selling for $4.99. The Mac version, by comparison, is $39.99 regularly, but $19.99 for a limited time.

This price difference is a bit confusing. Other than some minor design differences, both versions are pretty much the same. And while I recognize that Mac applications are usually more expensive than those for iOS, $39.99 is a lot to spend for a new journal program.

Is It Worth It?

Day One 2 is a powerful application that’s pleasant to use. For me, the new features are enough to justify paying for the product again. However, the average user might not feel the same way, especially when the Mac version is $39.99. Fortunately, you can have your cake and eat it too.


You can purchase Day One 2 for iOS and still use Day One Classic on your Mac. Sure, the new features won’t show up on your computer. Your actual journal entries, however, won’t be affected. Just be sure to use Day One Sync for backup purchases, not Dropbox or iCloud. If you favour writing on your iPad or iPhone and simply need occasional access to your journal on a Mac, this is ideal.

Don’t want to upgrade? For now, Day One Classic is still being supported and it’s still available for purchase from the iOS App Store. New Mac users, however, must buy Day One 2 on the Mac App Store.

Will you be upgrading to the new Day One?

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This article may contain affiliate links, which pays us a small compensation if you do decide to make a purchase based on our recommendation. Our judgement is in no way biased, and our recommendations are always based on the merits of the items.

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