I’m a fan of Day One, the diary/journal app. I think I first saw it and tried it after seeing Jack Dorsey writing about it on Twitter. Over the past few years I’ve used it sporadically and posted something like 120 entries. Not that many, in other words.
I think keeping a journal, diary, or something like it is really worthwhile if you can get comfortable and not overthink a daily or semiregular entry. Even a casual glance at some of the stuff I’ve written over the past few years instantly brings me back to specific moments in time, and specific people and places that have fled from my active memory. So I imagine returning from time to time to those entries will grow in value with every year.
Each entry can tell a story, but given time each entry also serves as perspective. At a time when Americans supposedly have fewer intimate friends than ever before, even self-perspective can be valuable.
But a major stumbling block for me in writing more regularly has always been time. I think the best time for an entry is at the end of the day. And at end of the time, I’m tired. Thinking about writing even 50 words is often daunting.
What I would really like to see is for Day One and others to incorporate audio/video entries. Writing is great, and probably the most timeless. But it seems like a simpler thing to record a one or two minute stream of consciousness style recap as an entry. Like writing, it’s something that can be done from any device. And in the case of the Apple Watch, it’s an example of a new paradigm.