[Day One] Who are you and what do you do?
When and why did you start journaling?
If we’re truly looking back, I suppose I was really rather young.
As you’d expect, I never wrote consistently, nor did I have too much fun. Instead, the allure of journaling resided solely within the novelty of having a private—sometimes secretive—document of some kind.
In that light, I frequently bought different books to serve as repositories for my thoughts, but I did little in the form of useful, cathartic reflection. Naturally—without an emotional connection—I steadily grew more-and-more distant from the prospect over the years. Whether for lack of time or interest, journaling stopped coming to mind as an outlet.
It wasn’t until I began writing online—many years later—that the prospect reasserted itself. Writing OneThirtySeven, my sometimes-active weblog, shared many characteristics with journaling. It was an intensely personal outlet for my thoughts—albeit one with a present audience.
As I was engaged in writing and sharing, I became increasingly conscious of precisely what I did not want to share. I tested the boundaries of comfort and public accountability and, in doing so, illuminated the topics and ideas that were best suited for a more private medium.
It was around that time, poetically, that Day One was originally released.
So, in other words, I started journaling properly because I needed a place to confront my innermost thoughts. I could share my opinions regarding business and the like on OneThirtySeven or Twitter, but I realized I was in equal need of a repository for myself and no one else.
What is your journaling routine?
As with so much else in my life, I have little structure or routine around my journaling.
I frequently skip several days without a thought. In the aftermath, though, I’ll find myself committing 2,000 words to an entry.
More recently, with the launch of Need, a good friend encouraged me to begin journaling much more. She explained that these memories would prove to be extremely important as my life progressed. That these early days of pursuing a passion would inform much of what I do in later life.
So, I’ve been actively trying to write at least once per week. Or, failing that, whenever I feel something important has happened I’ll immediately seek to commit it to Day One.
Do you focus on longform writing, or in capturing small memories of life?
As I’ve said, the allure of journaling comes in the form of catharsis. Rather than reflecting on inconsequential elements of my day, I often use Day One to parse my way through the complexities of a relationship or a discussion.
When I was raising money for Need, for example, I used Day One as a means to review discussions I’d had with investors. In doing so, I’d turn over the quality of the various personalities, their business leanings, and, ultimately, I’d be able to uncover whether they were genuinely interested in an investment or not.
There’s obviously value in capturing small moments, but, for me, I’m typically focused on more therapeutic conversations with myself.
Do you have a favorite spot you like to journal from?
I’m writing this early on a Sunday morning—fresh coffee at my side—in my dark apartment. My girlfriend is reading quietly in the next room, whilst I’m sifting through some early-morning thoughts.
I’d say that precise scenario is broadly indicative of my typical habits (i.e., early, dark, and secluded).
The only variable that changes is the precise location, which oscillates between my apartment and my office. For the former, as with today, it’s exclusively early in the morning. For the latter, it’s exclusively late at night.
What was your first entry in Day One?
It was, apparently, August 3, 2012. (Although, upon reflection, I think I may’ve started and restarted—literally wiping the slate clean—several times prior.)
I was in London—my home—visiting my friends and family. I was going through a fairly tumultuous year and, at the time, was meeting with various different companies about ongoing relationships.
On this particular date, I was reflecting on two projects I’d been approached to run and, later, an evening out with friends. Sadly, it wasn’t anything particularly remarkable.
The following day’s entry—more interestingly—was my reflection on my visit to the London 2012 Olympics with my family. I was resoundingly hungover—likely from the aforementioned “evening out with friends”—but documented much of the emotion and pride of that day.
How many entries do you have in your journal?
Not too many given the time I’ve been using the app. Roughly 100, I believe.
Today, it’s increasing rather rapidly, though. (And, fortunately, the average length of entry is decreasing.)
I’m currently writing about three entries per week.
What is your favorite, or most used feature from Day One?
The integration of photography is what first made Day One invaluable for me.
I’m not much of a photographer, but I do take quite a few photographs of inconsequential aspects of my day-to-day experiences—the vast majority of which are not up-to-par to be published anywhere publicly. They are, however, useful indicators of what I’d been doing on a particular day.
Day One allows me to provide context for those fleeting moments. And, these days, I often find myself looking back over former entries and seeing the photographs I included. That’s, more often than not, my most favorite part of the experience.
I’ll stumble across a photo of the exterior of a restaurant before a meeting and then read about the details of that discussion. Or, I’ll happen across a photo of a coffee I had on a quiet, reflective morning.
I truly love that aspect of Day One.
Do you write mostly on the iPhone, iPad, or the Mac?
Almost exclusively on the Mac.
I love the notion of writing on my iPad, but that’s used for little more than some light reading these days. Equally, I have Day One on my iPhone’s home screen, but don’t often think to write with that form factor.
With my Mac, on the other hand, we’re rarely apart. It’s the medium through which I feel most comfortable writing and working and, in that instance, I’m only a click away from Day One at any given time.
Historically, I’ve always had the menu bar icon switched off. More recently, however, I’ve found that to be a great means for logging quick thoughts and reflections. That has really made a big difference.
Do you follow any journal organization rules?
Again, as with so much in my life, I love the idea of rigid organization and structure, but I’m more realistically living in some semblance of mild chaos at any given time.
For those who are familiar, the best explanation I can provide is the feeling when you visit a Container Store—an American shop for organizational products—and suddenly feel an infusion of confidence that you can become so much better and more efficient by simply seeing (or buying) these products. That’s precisely how I feel when I think about applying some sort of structure to my journaling and productivity. In reality, though, I cannot function in such a fashion.
So, no. There are no rules to my journaling whatsoever.
Have you ever relied on Day One for something unexpected, or used it to recall details about a specific event or date?
As I mentioned, I’ve been using Day One to keep track of my various business relationships. From investors to photographers, I often reflect on various personalities within Day One.
So, recently, I was approached with an investment offer and used Day One to remind myself of the particular gentleman’s personality before accepting anything. (I ended up not accepting the offer as I’d remarked to myself that I ought to never go into business with him several months ago.)
Similarly, people frequently ask me about the genesis of Need as a concept. And, truly, much of what Need has become was committed to a Day One entry in December 2012—one that has proven to be invaluable for the past year or so. I often find myself returning to that entry to remind myself about the early moments of the concept and the values that informed its inception.
You recently said that you went through a long period without journaling, only to miss it immensely. What made you come back to writing in Day One?
The reason is twofold.
The first—and much less poetic—reason is that Day One is fundamentally a beautiful piece of software. I’m drawn to quality products—particularly those that are able to instill an emotional connection—and Day One is at the forefront of that pack in my digital life.
The second reason is that I felt out of touch with myself.
2013 was a whirlwind. I went from deciding between two job opportunities to raising funding in a matter of two weeks. Similarly, I went from working quietly from home to being apart of a community at WELD. My schedule changed, my friends changed, and I was suddenly being drawn to go to far more events, meetings, and parties.
I rarely found a moment to reflect about what it was, exactly, that I was doing with my life.
So, somewhere along the way, I started committing huge chunks of my day-to-day life to Day One once again. And I’ve stuck with it since.