How I Use Stuff: Day One

My journaling workflow has evolved a lot over the past few years. My very first entry in Day One is from June 21, 2012, but I didn’t start keeping a regular journal till early November 2015, shortly after I quit drinking. I turned to keeping a journal as a way to organize my thoughts and feelings in a place that I knew was private and non-judgmental. Since then, my usage has largely stayed the same, although I’ve been able to be much more consistent in the past year. I’ve also added a number of smaller semi-automated entries to my practice.

The Workflow

As of this writing, I have a grand total of 2,144 entries stored in Day One. Those entries are split up across a few different journals:

Journal (1,191 Entries)

This is my “main” journal, and is where all of my free-form writing goes. I don’t have any hard and fast rules about this journal, and it’s littered with photos of graffiti I see while traveling, dumb jokes that I don’t feel like posting publicly, and longer form entries. I try to write at least one of those long-form entries in here every day.

The format for my daily long-form entries has gone through multiple revisions over time. When I first started keeping a journal, I wrote several entries each day, each with a specific topic. I wrote one about my workday, one for my personal thoughts/feelings, and one for each activity I did. That pace wasn’t maintainable, and it became exhausting. I eventually whittled that down to just writing a single large daily overview entry, but got a bit burned out on that as well.

More recently, I’ve settled into just writing something in here every day. I try hard to not judge myself on length or quality of the entry. Instead, I just focus on getting something written down. I’ve moved away from entries that are glorified lists of things I did during the day, and I focus more on writing about what I feel. One of the biggest benefits of journaling for me is being able to look back at where I was years ago and see how things have changed. The list-style entries have limited interest as time goes on, but the entries that center around my feelings and general outlook are evergreen.

Daily Q&A (651 Entries)

When I started my journaling practice, one of the things I wanted to replicate the most was the Daily Q&A Journal that I bought for my wife nearly 4 years ago. It’s a 5 year journal, but the questions repeat every year on the same day. As you go through, you answer the question, but you can also look up to see your answers from the previous years. It’s an amazing way to watch your responses change over time. However, carrying around a physical book for that was a non-starter for me. Thankfully, Day One has an excellent “On This Day” feature, where it shows you all the entries you wrote on the current day of past years. So all that was left was to add prompts.

After painstakingly transcribing every question in the above physical book and translating them into JSON, I was able to publish a super small web app to spit them back out at me (the source is public if you’re interested). This lets me outsource the prompts, while using Day One’s own features for the yearly reviews.

I’ve managed to stay super consistent with this, and have gone 417 days now without missing a question. It’s interesting to see my answers from the previous year, and to see how they have changed. Also entertaining are the days when I think of an incredibly clever answer only to realize it’s the exact same thing I wrote in a previous year.

Productivity (154 Entries)

There are two types of entries that go into this journal: Daily and Weekly productivity entries. These entries are similar to my Q&A entries, except that they ask the same questions each time:


  • What was something important that you accomplished today?
  • What is one thing you’re thankful for today?


  • What were your accomplishments, highlights, and wins from the week?
  • What were your failures from the past week, and how could you improve on them?
  • What were your loose ends for the week?
  • What did you learn or discover this week?
  • How are you coming along with your overarching big goals and projects?

I’m prompted to write these as a part of my daily and weekly reviews. I have Workflows set up for guiding me through the prompts and adding them to the right journal with the right default tags:

This is the newest addition to my practice, and it’s one I’m still refining. I don’t remember what prompted me to start these, but I’m on my 4th month of writing them, and I’ve been enjoying it. Initially, these entries lived in my main journal, but once I decided that I wanted to make it a regular practice, I created a new journal to hold them.

Writing these has been a nice addition to my practice. The idea is akin to gratitude journaling, but calling it “Productivity” journaling helps me keep from getting all fluffy with the entries. It’s a nice way to regularly remind myself of the things I’m getting done and the things I’m enjoying. The weekly entries give me a chance to reflect on my successes/failures from the week and helps me come up with a plan to continue/fix them.

Home Screens (78 Entries)

Every month I have a recurring task to take a screenshot of my home screens for my iPad, iPhone, and Apple Watch and dump them in here (with an appropriate tag). I love the idea of keeping a monthly record of what apps I’ve allowed to live on my home screen. It’s also nice to relive these old setups on the first of each month, when “On This Day” surfaces them again.

Social (32 Entries)

The entry count here is artificially low because I still haven’t gotten around to importing my backlog, but this is essentially a local copy of my microblog. It’s currently being populated via an RSS trigger through IFTTT. I wish that Day One had an API so that I could hit this directly, but until that exists, this will have to do.

Reading (38 Entries)

This is also populated via IFTTT, and is intended to be a sort of Commonplace Book, where all interesting quotes from things I read are kept. Unfortunately, it’s incomplete right now because I can only populate it via Instapaper. My Kindle notes/highlights are siloed away inside Amazon’s data centers, and they don’t seem to be particularly interested in letting them out. It’s a real shame, I’d love to be able to export those easily (and automatically).

As it stands, any time I make a highlight in Instapaper an IFTTT applet fires and an entry is added here.

On Journals and Tags

One common point of confusion/contention with Day One seems to be when to use journals and when to use tags. The approach I’ve taken is to create journals when I’m posting about specific thing often enough that it begins to clutter my main Journal. So for example, I wrote my productivity entries inside Journal until I decided to do it every day. At that point, the entries started cluttering that journal and so I moved them all out into their own Productivity journal. This gave these entries a place to live while also removing the noise from my main Journal.

Tags, on the other hand, I’m fairly loose with. I create them almost at will. I have some common ones that I add to larger topics (for example, travel/2018/europe or work/square), but others are added arbitrarily. I don’t put too much time into thinking about them, and don’t have a great strategy for how to manage them.


You might have noticed that I’m using a number of tools to overcome some shortcomings of Day One itself. I’d love to reduce the number of external tools I use to make my practice work, but I’d first need some improvements to Day One:

  • Template Support. Ideally, templates with multiple prompts. This would improve so much about my practice. One of my biggest pain-points right now is that since Workflow is on iOS, it means I have to switch to my iPhone in order to do those daily/weekly productivity entries. This is especially annoying for the weekly entries since those can get long, and I’d much rather write those on a full keyboard instead of in an alert on my iPhone.
  • External API. This can be (should be?) write only, and could (should?) work only with unencrypted journals, but direct API access would let me feel much better about things like my microblog entries. Being able to control the content without needing to go through IFTT would mean I could ensure that my entries are formatted consistently. It would also fix the fact that IFTTT “helpfully” strips HTML from any passed text.
  • Location-only entries. Or, alternatively, a quicker workflow for adding location-based “check-ins” to a specific journal. This could also theoretically be achieved if the external API existed, since I could write a small wrapper app that posts a location to Day One and Foursquare simultaneously. Either way, I’d love to get these into Day One for archival and the existing methods of adding location based entries don’t cut it for me.