DayOne is the last diary you’ll ever need

spotlights unexpected items that make our daily lives just a little bit better.

There they sat on the groaning shelf, looking like a rebuke to the entire digital era: years of handwritten journals. Some were slim notebook folders, but most were hefty tomes — half-scrapbook, half-angsty accounts of my school and college days, or bulging clips of magazine bylines. All were annoyingly irreplaceable pieces of personal history I’d carted around from house to house over the years like a ball and chain. 

So far, they had flagrantly refused to digitize themselves. But I wasn’t sure if I should digitize them, either. The reason sat next to them: folders full of printouts, equally unique. 

Here were old computer diary entries, online articles from the 1990s, e-mail exchanges with loved ones. Each had been digital once. Each had been corrupted or vanished in years of transfers from hard drive to hard drive to hard drive. Some web clips had vanished even from the Wayback Machine. Good thing I’d printed them out! Don’t ever rely on ones and zeros, the folders seemed to whisper.

So it’s a little surprising, a couple of years later, to find that I’ve digitized the heck out of all those diaries and put them into a journaling app called DayOne. Why? Because DayOne makes it seductively easy to write secure, backed-up entries from most any device — Mac, iPad, iPhone, Android phone — and also makes it easy to insert any kind of legacy stuff (including photos and PDFs) into entries for any date in the past. 

I’ve gone all in on this One Diary to Rule Them All, even though it’s a subscription service, costing $35 a year or $3 a month. I generally hate subscription software, and it took a while (plus assurances I’d still own my data if I ever stopped paying) for me to take the plunge. My conclusion: If you’re a casual journal-writer, it may well be worth it. If you’re a hardcore diarist with an extensive archive, it’s absolutely worth it. 

Silicon Valley is eager to build a file on you. You may as well be the one with the most comprehensive file

DayOne has come a long way since its first, non-subscription Mac-only version in 2012. The developers, Bloom Built, spent years ironing out the kinks in making the diary sync across Mac and iOS using Dropbox. It offered encrypted entries with a TouchID or passcode lock, searchable tags, and a useful Mac toolbar icon so you can start typing in one click. 

The subscription version arrived in 2016 and added a dedicated DayOne syncing service plus the ability to have multiple images in a single post. You could now also write in different journals for different activities. 

Recent updates have added Dark Mode, essential for late-night worry-unloading entries. Thoughts plaguing your sleepless brain at bedtime? Grab your phone, launch DayOne, start typing and watch the tension drain out. DayOne will automatically append the weather and temperature at your location, which could help your future self understand why you were so cranky that one time. 

Know thyself

Most importantly, DayOne plays well with others. Via IFTTT — an effortlessly easy service for connecting apps — DayOne now automatically captures my tweets, Instagrams, Facebook posts, the Spotify tracks I favorited, my completed tasks via ToDoist,  my sleep hours and daily step totals via Fitbit, even the time I spent on various categories of programs and websites via RescueTime. 

All these data go in separate journals — Social Media, Health, Productivity — so as not to clog up the main diary feed. Hey, in an age when half of Silicon Valley is eager to build a file on you composed of your various digital doings, you may as well be the one with the most comprehensive file, right? 

If you’ve read this far and are nodding enthusiastically at this point, you’re likely an obsessive self-historian and incorrigible digital hoarder yourself. And you’ve probably also wrestled with this question: With all this content you’re creating, when are you ever going to get a chance to look at it again? 

The answer is contained in what I consider to be the finest new DayOne feature of all: “On This Day,” which is exactly what it sounds like. Everything you wrote on this month and date in years past is shown in the same place. Now that my old-school diaries are in DayOne as well (I turned them all into PDFs in a few weeks using my iPad and a camera-based scanning app called TurboScan), my “On This Day” literally stretches back decades. 

I usually skim through this section first thing in the morning, and it provides the most extraordinary perspective. Imagine one of those halls of mirrors where you’re reflected back and forth dozens of times in the same space, but each one of those reflections is you at a different age. 

Sometimes you see almost spooky coincidences and connections between these reflections. Often you realize you’ve been chasing phantoms for years — worrying the same baseless worry, vowing to build the same good habit — and it galvanizes you to make a necessary change. 

Now my diaries and computer files are quitting the groaning shelf for archive boxes that will sit in the basement: the ultimate backup. I’m still wary of putting all my historical eggs in one basket, and I do worry what happens if Bloom Built goes out of business or their servers get wiped. Which is why I basically have a backup on every device I own.

A fondness for backups also explains why I’m keen to try a DayOne feature that’s currently available in beta. The company now prints books to order, each book containing journal entries you specify. Prices start at $15 for 50 pages in black and white, and go up to $55 for 400-page books in color. Excluding most of those IFTTT-connected entries, I could easily fit a whole year into a printed book.  

If you get the 400-page book annually, that comes out to $55 a year, plus $35 for the subscription, which really isn’t all that much to pay for peace of mind that your personal history will always be around. Or to ensure that you will continue to tell the story of your life, in all its messy, emotional, angst-ridden, triumphs-and-failures glory, long after you’re gone.