Want to Keep a Journal? Go Digital

I’ve kept a personal journal for most of my adult life. These journals have helped me wrestle with every significant decision and manage through the many stresses of everyday life. Last month, I put down my millionth word in over 40 years of self-reflection.

I’ve written about the reasons to keep a journal, and by far the most frequent question I receive from readers is how to establish a regular habit of journaling. Many find it easy to start a journal but much more challenging to keep it up.

For years, I purchased attractive leather-bound journals to collect my thoughts, but some of these books took years to fill with my slanted, left-handed scrawl. There were a couple tumultuous years in my twenties when all I could muster was a single angst-ridden entry. It wasn’t until I moved to a remote island where I was forced to take a solitary ferry ride to work each morning and night before my journaling habit took hold. Watching a storm-tossed sea out the cabin windows of a ferry boat put me often in the mood to write.

Now, I realize that taking a ferry boat to establish a journaling habit isn’t practical for many people. However, I did learn something else about my journal keeping that might be more useful.

Eight years ago, I tried the Day One app to see if a digital approach might replace my cherished leather-bound books. Day One was one of the first journaling apps to come out for both the Mac and iPhone/iPad. My first entry wasn’t particularly optimistic about this new technology:

I think writing here in this way will have me more focused on the device than the words. Hard to imagine myself getting into the writing zone like this, always worrying about hitting the right keys … Still, it is convenient, tapping away as I am now from my easy chair, writing this entry on my iPad instead of surfing web sites.

Journal entry: December 12, 2012

Despite my initial uncertainty, I adapted quickly to a digital process. Since 2013, Day One has been my sole journal writing tool, and I would never go back to hand writing my journals. A few years ago, I transcribed my old paper journals into Day One for digital safekeeping and to revisit my youthful writing. With all my journals reduced to ones and zeros, I recently measured my productivity before and after switching from paper. Here’s a chart of my journal entries over a long span of writing (eight years on paper, eight years using Day One):

In my final year of paper-based journaling, I wrote 33 entries. That’s a little under once a week. My journal output shot up five-fold in my first year of using Day One. Comparing eight-year time spans on both systems, I wrote four times more entries in Day One than on paper. Over the past couple of years, I’ve written just about every day in Day One. On top of this, I share more each time I write in Day One. My typical paper entry ran 300 words. In Day One, that has increased by 20 percent, now 365 words.

After all those years of writing on paper, how did Day One make me a more prolific journal writer?

I think the most significant breakthrough for me was ubiquitous access on mobile devices. I usually kept my paper journal in the glovebox of my truck, where I wrote during ferry crossings across Puget Sound. As a result, I seldom wrote at home, or at work, or on weekends. With Day One available on the Mac, iPhone and iPad, I could capture thoughts in many more places and times. I grew especially fond of writing on the iPad with its compact size, always-connected cellular radio, and comfortable keyboard. Last year, nearly 100% of my entries were written on the iPad.

Unlike a paper journal, Day One allows practically every form of digital communication to become part of a journal entry. Emails to friends and family, Facebook posts, and blog posts are just a copy and paste away from my journal. And of course, I can add photos. I have over 500 photos, videos and sound clips in my journal that bring a whole new level of intimacy that simply wasn’t possible in my old paper journals.

After I transcribed my old journals into Day One, I realized I had the ultimate personal knowledge system. Almost everything important that happened to me in the past 40 years is accessible with a quick search. What did my doctor tell me at that visit back in 2005? I can easily retrieve it. What were my daughter’s first words? I wrote about it (today, I would have recorded it!). I apply tags to my entries, which makes it incredibly powerful to review my personal musings on themes like fatherhood, marriage, spirituality, travel, etc. All of these thoughts were buried and locked away in my paper journals but are blissfully free in Day One. It’s become an incredible resource of information and insight about myself, which in turn has become a positive reinforcement loop to keep recording my thoughts.

Some other reasons that drew me a digital tool like Day One:

• Data encryption and on-device security makes my electronic journal much, much more secure than a book I carry around. I once left my journal in a hotel room in Atlanta. It took a half dozen calls and six weeks to recover it. Needless to say, I was mortified at having my private thoughts pass through a stranger’s hands.
• Day One offers daily journaling prompts, which help you if you’re unsure what to write. A few of these took me to unexpected places and developed into some of the most memorable entries.
• I’m able to time travel each morning as I read my “On This Day” entries. Day One pulls together every entry across all years from the current day into a special layout for review. Reading about my life in my own words from 25 years ago to the present day is incredible and frequently humbling.
• Day One adds meta-data to each entry behind the scenes like location, weather, and even what music you were listening to while you wrote. The world map of all the places I’ve journaled is fun to review.
• And finally, my journal entries can be exported into various formats as a backup in case Day One ever goes out of business. For example, I opened my lifetime of journal entries in Microsoft Word to calculate the writing statistics I cited previously.

If you keep buying attractive blank journals, but struggle to fill them, you should give a digital option like Day One a try. Set a daily reminder and take the few minutes you might otherwise spend on social media to write to yourself. Write about the big things in your life, but also the small, precious things. Or answer the day’s writing prompt. You might be surprised at what you share. And trust me: your future self will thank you.