Dual-Device Day One Journaling for Free

Felix Wong's avatar
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I started journaling daily for the better part of the last nine months. I was partly inspired by friends who have adopted the habit. For example, I once asked my friend Adam whether he had met the brother of someone I crossed paths with in Pontevedra, Spain. This brother was on the Stanford cycling team and had attended Stanford at roughly the same time as Adam and I. I knew it was a long shot, and sure enough, Adam did not immediately recognize the name.

But he later searched his journals and—incredibly—found a match. He had met the brother at a user group for Palm users (if you remember those Personal Data Assistants) of all things 25 years prior. He even noted the bicycle the brother was riding. Such detail and memory nearly brought tears to my Pontevedra friend’s eyes when I relayed the information, since his brother had passed away in the early 2010s.

Later, another friend of mine, Eric, showed me his organizational system. He could click on any day on his calendar and quickly see what he did that day and what photos he took. This seamless time travel was only made possible through journaling.

I had never journaled until now as I figured that the blogging I have done (since 1995!) was functionally identical to it. But truth be told, I do not blog every day, plus I only blog about a small subset of my life that I want to remember for the future or share with the masses.

I realized that journaling would not only help me retrieve memories from the past but also keep me accountable to my goals and review how I spend my limited time on earth. Also, journaling daily often makes it a lot easier to blog later since I already have many things written down!

The Benefits of Journaling with the Day One Journal App

Beyond preserving history, journaling acts as a highly effective, free therapist. It improves memory retention, boosts mindfulness, and provides a safe space for emotional processing. Thankfully, I rarely suffer from anxiety, but pouring thoughts onto a digital page can easily defuse a spinning mind. It also clarifies muddled thoughts for better decision-making.

I started using the Day One journaling app because it seems to be the most popular one, boasting stellar reviews on the App Store. I tried it out and was happy with the elegant interface, which even accepts Markdown as an input method. I also did enough research to assure myself that if I wanted to migrate to a different system down the road, exporting from Day One would be a doable endeavor—which is not the case with other journaling apps like Apple’s new-ish one called Journal.

The other crucial feature I checked before committing to Day One was whether I could use it on both my iPad and iPhone without a subscription. Day One advertises that one of the perks of a paid plan is the ability to “journal across all your devices” with seamless syncing. The implication is you cannot accomplish this without opening your wallet. That would have been a dealbreaker for me. Even though I journal 95% of the time on my iPad Pro, I could envision scenarios where I wouldn’t be hauling around my tablet. For example, short travel trips.

Fortunately, there is a way to use Day One on both devices completely free. I’ve been using this method for the last nine months and it works well.

Free Dual-Device Journaling

The key is to use the Day One app on one device: your primary one. In my case, that is an iPad. Then, you use the Day One website on the secondary device (for me, an iPhone).

The only drawback of this method is that you need Internet access when using the Day One website on the secondary device. It is not true syncing between the two devices. Rather, the primary device syncs to the cloud, and the website reads directly from the cloud. In practice, this is not a huge hindrance as I almost always have internet access. When I don’t (e.g., on an airplane), I’d write the journal entry offline in Apple Notes and then copy and paste it into Day One when I’m online.

To make the website function more like a native app on the secondary device, I save the website to my home screen as a web app. I recommend you do so too.

Setup Procedure for Users with iCloud

If you used iCloud, Day One probably will have saved your encryption key to it. It did for me when I first set it up nine months ago.

If this is the case for you, follow the steps below.

  1. Go to dayone.me in Safari.
  2. Hit the share button in Safari.
  3. Select Add to Home Screen. Make sure Open as Web App is toggled on.
  4. Find the app on your home screen and open it.
  5. Log in.
  6. No journal will be shown, but click on the menu button in the upper left. A menu in a left-hand pane will slide open, and towards the bottom will be “1 Locked Journal Hidden. Click to unlock journals with key.”
  7. Retrieve your encryption key to unlock your end-to-end encrypted data. Sign in with iCloud to finish the process.

You are good to go. You do not need to sign in again in the future.

For Users Without iCloud

If you do not use iCloud, Day One will not have saved your encryption key to the cloud automatically. You will need to obtain and write down your encryption key manually.

  1. On your primary device, open the Day One app.
  2. Navigate to Settings, select Sync, and tap Encryption Key.
  3. Choose an option to copy the key to your clipboard, email it to yourself, or save it as a PDF.
  4. Now follow the procedure in the preceding section. But when you reach Step 7, manually enter this key instead of tapping the iCloud button.

Happy dual-device journaling!