500 Days in Day One

500 Days of Diaries

500 days (and 23 years) of daily diary keeping—a résumé.

Last night, I filed my 500th consecutive entry in Day One.

I’ve been journaling since 1989, never skipping more than a day or two between entries, often spending more time agonizing over the analysis of the things that happened than the things themselves. My diary was my first attempt at a “Quantified Self”, with daily stats, weekly tallies, and monthly analyses of my perception and inaccurate recollection of sleep, diet, exercise, and mood.

Roughly a decade later, around the time I moved to the US for good, I switched to an electronic journal. A small Sun Workstation in one of the datacenters at Exodus Communications became a haven of sorts, hosting not only an ever-growing text file of almost daily diary entries, which was nothing more than the same navel gazing, cleansed of deep thoughts about my mental health and lacking the more vivid details of dates, hookups, and work related excitement.

In 2004 I moved the diary to a hidden category on my blog. Instead of using two apps, I now just used the web frontend for both.

In 2005 I drunkenly agreed to become employee one at WordPress Inc (later Automattic) and bought a MacBook, which added more mobility to the setup but it also was the same year I started to leave dot.com for good, joining Blizzard Entertainment as a Story Developer on World of Warcraft. That could have been a perfect cue to write more, being at Ground Zero for the launch of what would become one of the most successful AAA MMORPG titles on the market, but I spent most of my time playing the game when I wasn’t studying or working for the company making said game.

That changed in 2012 when I not only left the Silicon Valley and all technology-for-money work for good, but Apple named Day One a “Mac App of the Year” or something like this, and so I made the final switch. Day One’s early days were amazing for many reasons: a module called “Publish” allowed me to continue as I had before, writing two entries, one a sanitized version of the other, and publishing one.

This approach ended in 2016 with Day One 2, which took away this functionality (maybe Automattic’s acquisition will restore it), but that was just as well. Facebook and Twitter had effectively killed ego-blogging, dropping visitors to my site from around 6000/week to less than 100. I’d also become active on Quora in 2011, writing answers and stories, which meant I had less and less use for a public blog. And with than, some time in 2016, I stopped blogging in earnest, trying it a few more times over the years, but never really coming back to it. My diary, on the other hand, remained.

The begin of the pandemic in earnest in March last year made it clear, that I had to keep an inventory of my mental health. I’d been struggling with depression off and on since the first days of my first attempt at a medical degree in 1992. Then, as now, the diary helped me in keeping my mind in check, giving me that much needed “reality check” level of self-assessment.

I fully intend to fill the 1000 and beyond. But this milestone, 500 days of continuous journaling, an average of 450 words per day, was worth looking back and celebrating the 32 years of keeping my mind in check and my thoughts accountable.