On January 1, 2016, I started a daily journaling habit. As of today, I now have 2000 daily entries – a continuous run for over 5 years1. 🎉

My “journal” started as an accidental offshoot of one of my early Quantified Self projects. The goal was to keep a log of how I was feeling each day, so I could look at trends over time. My first “journal” was a Google Sheet with three columns: “Date”, “Daily Rating”, and “Notes”. Each day, I’d rate the day from 1-10 and write down a few notes about what happened. To be clear, this was intended as a data collection experiment – the real data was the daily 1-10 rating, and the notes were just incidental flotsam that maybe I’d data mine later.

As the habit evolved, I felt that my recorded “ratings” were less and less meaningful. Most of my daily ratings ended up being in the 4-6 range (I tried to normalize around 5). Trends were hard to spot, or so obvious as to be not worth noting (e.g. I tended to rate my days as higher when on vacation). The qualitative notes, however, became more and more meaningful. They weren’t just fun to read in retrospect, they were also valuable to write. Adding a reflective moment in the evenings is a great way to cap off the day.

In 2016, I would only write a sentence or two each day as notes. This increased over time, to where I now regularly write 200-400 words each day. The entries are casually written, mostly in stream-of-consciousness, and very lightly edited. It helps that I’m much faster at typing than hand-writing – digital journaling is closer to a raw stream of consciousness than writing would be, since I can type closer to the speed of my thoughts. Typing an unedited 400 word entry takes me 5-10 minutes, at most, and has become the last thing I do before logging off in the evening.

In 2020, after 4 years of using Google Sheets, I finally got sick of writing a journal in spreadsheet cells. Spreadsheets are not text editors. Spreadsheets lose your input if you click “Escape” at the wrong time, forcing you to rewrite everything from scratch. Do not make the same mistake I made, trying to write prose in spreadsheet cells. I migrated my existing entries to Day One2 and haven’t looked back.

When I switched to Day One, I also ditched my “ratings” system. Now, I just have a journal – which, in retrospect, is the most valuable aspect of the habit. Day One also has some nice features, like the ability to maintain multiple journals, allowing me to write separate Weekly and Monthly reviews. I also get stats from DayOne, so I now know that my entire journal sits at around 320,000 words. (Yikes, that’s a lot…)

I’ve written in the past about the potential downsides of habits. I was reminded of this again by Marcus Crane’s post, Let your streaks end naturally, especially with this looming streak milestone of 2000 entries. Over the past few years I’ve grown suspicious of daily habits that feel like “requirements”. Rigidly maintaining habits can be self-limiting. However, I’ve never really felt this about journaling. The journaling habit does require some “work” to maintain, but the benefits are substantive enough that it feels like one of those “keep your room clean” habits which have minimal risk of overdoing it.

Journaling isn’t magic. I still forget stuff. Some days I feel less inclined to write an entry than others. But having something is better than nothing. Taking a few minutes to reflect on the contents of your day acknowledges the value of time, and rewards your future-self with a glimpse into your thoughts of days years in the past.


  1. That’s not to say that I literally journaled every day for the past 5 years. I definitely lapsed a few days here and there, but (so far) I’ve always returned and backfilled entries for those days. ↩︎

  2. The week I’m writing this post, I learned that Day One was acquired by Automattic. I hope they keep their acquisition-time promise of maintaining “the preservation and longevity of Day One”. Time will tell… 🤷‍♂️ ↩︎