Keeping a Diary

I started college in fall 2007: just after the iPhone was announced; in the midst of Obama and McCain’s campaigns for president; and at a time when newspapers printed[1] dire headlines about the impending financial crisis.

Fuck. That was like, eight years ago.

And I didn’t keep a diary; only an archive of my defunct Facebook account remains. I’m kicking myself today because I have a dwindling recollection of specific conversations, meetings, and events I experienced during those formative years.

GitHub engineer Zach Holman writes about a similar regret in his excellent article, Keeping a Journal:


  1. Yes, printed!  ↩

I started a journal in high school, but mostly stopped in college. It kills me that I didn't write during the first few years in the working world. It almost feels like I didn't even live those years.

And consider Apple SVP Eddy Cue, who has only one regret from his company's years'-long ebook price-fixing case: "If I had [the case] to do all over again, I’d do it again. I’d just take better notes."


For me, a diary is an essential medical tool that tracks my ongoing recovery from a major depressive episode. And because I'm a nerd who's averse to unnecessary typing, I decided to create a template using a combination of Markdown, TextExpander, and Day One.

My goal was to remove as many friction points as possible, so I could quickly get into the habit of writing. I'll break this process down in a second, but it's easier to just watch this 25-second-long demonstration to see what I'm going on about.

First, I wrote a template in Markdown. Markdown uses a plain text format, so you can write it in any old word-processing application; I prefer to use Byword (pictured below).

Second, I copied and pasted this text into a new TextExpander entry. It looks kind of messy, but it's fine as-is. The only things I added were an auto-date-fill-in field at the top and single-line fields for all of the morning questions. This allows me to quickly Tab through and complete each field, without interruption, and without resorting to mousing over to the end of each line like an animal.

I decided to use the abbreviation ;daily, so when I type that anywhere on my Mac, it will immediately expand this wall of text. Starting off the abbreviation with a semicolon prevents spurious input, and I like to think that the word "daily" tricks my brain into using this, um, daily.

Finally, I open my journaling app of choice, Day One, type my new favorite phrase, ;daily, and fill in the fields. Press Return or click OK. And you get something like this:

It's OK…

It's OK…

Day One has quite a few neat tricks. Like its ability to convert Markdown so things look pretty.

Now it looks pretty! :D

Now it looks pretty! :D

You may have noticed that I added #Medical at the end of this wall of text. In Markdown, a single hashtag generally indicates that that text should be a heading. However, Day One actually reads a hashtag followed immediately by a word (that is, when there's no space between them) as a tag. So all of these entries, which I'm ideally creating every day, are easy to filter and search.

I guess I could have just done a simple copy and paste of a template, or found a crappy mental health spreadsheet online. But where's the fun in that?

I've posted the text below, if you want to give it a shot. But I'm open to suggestions on how to improve this method.


# Daily Progress %Y-%m-%d

## Morning

* Sleep Quality (out of 5): **%filltext:name=42%**
* *Tell me how you really feel.* **%fillarea:name=Let it all out…:width=30:height=4%**
* Went to bed around **%filltext:name=Bedtime%**
* Fell asleep around **%filltext:name=Sleeptime%**
* Woke up around **%filltext:name=Waketime% a.m.**
* Took MEDICINE XX (500 mg) at **%filltext:name=TIME% a.m.**

- - - 

## Evening
* Day's-End Feels (out of 5): 
* *What kind of shit did I accomplish?*
    *
* Took MEDICINE XY (200 mg) at

#Medical

UPDATE Jan 22: I got in touch with Zach Holman on Twitter.

I'll have to give the command line trick a shot later today. In the meantime, you can check it out at Day One's website.