Journalling with Day One 2.0

I've been using Day One (Day One 2.0 for Mac and Day One 2.0 for iOS) for a few years now, I think. In fact, I've just had a wee look, and the first entry that doesn't look like it was imported from elsewhere is just over four years old. In the time that I've used it, I've amassed 2,848 entries, though some of them have been imported from previous journalling experiments. I thought, since version 2.0 was released today, I'd try writing my first entry in it by explaining how I use Day One, what other tools I've tried in the past, and maybe even mention a couple of features I'm hoping will come to it some day!

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I’ve been using Day One (Day One 2.0 for Mac and Day One 2.0 for iOS) for a few years now, I think. In fact, I’ve just had a wee look, and the first entry that doesn’t look like it was imported from elsewhere is just over four years old. In the time that I’ve used it, I’ve amassed 2,848 entries, though some of them have been imported from previous journalling experiments. I thought, since version 2.0 was released today, I’d try writing my first entry in it by explaining how I use Day One, what other tools I’ve tried in the past, and maybe even mention a couple of features I’m hoping will come to it some day!

I think things through by writing them down. Some people think by talking — thinking out loud — but I like to have a clear idea of what I’m going to say before I say it. I find it easiest to do so by writing them out. It works for thoughts that I’m not trying to communicate with other people, too. I find that I can understand my own thinking and, to an extent, my feelings, just by committing them to paper. For the most part, I could then just throw away the bit of paper — it has served its purpose — but I’m a hoarder, and I’m loathed to throw things away, particularly when they can be cheaply encoded as bits and live in the cloud!

Enter Day One. It’s a journalling application for the Mac, and for iOS (it’s universal, so it works great on the iPhone and the iPad, including the new iPad Pro with the latest version!). Entries are timestamped, and you can navigate to old entries through a calendar. You can tag entries, and later search for entries with particular tags1. It also captures other contextual data around the time you create the post, including your location, your current activity (which is more relevant if you’re walking around with your iPhone), and the current weather conditions. I have a real interest in capturing contextual information around the time that you’re writing, so I’m keen to see what can be done with this metadata!

It has full Markdown support (including footnotes, which makes me very happy, though sadly Medium doesn’t let me replicate them here!) which I consider to be essential. I write in Markdown even in apps that don’t support it, going back later on and mucking around with formatting if I need to. It means I can focus on what I’m writing, instead of worrying about how it looks. The human brain isn’t really designed to consider both of these endeavours at the same time! We’ve been able to add a single image to an entry for a while now (though I rarely use the feature), but version 2.0 has brought the ability to add multiple images. Perhaps that’ll be a useful workflow for keeping track of what I’m up to when I’m out and about (instead of just sharing all the photos on Instagram!), or maybe I can use it as a way of selecting images to go along with a draft post destined for Medium.

The major new feature with 2.0, though, is that I can now have multiple journals. (I’m quietly hoping that the major new feature in version 2.1 is going to be that I can share certain journals with other people!) It’s perhaps worth talking about the two distinct purposes I have for journalling in Day One: morning pages, and keeping track of what I’ve been doing.

Morning Pages

I can’t remember who introduced me to the idea of Morning Pages, but it’s a habit I’ve been more-or-less sticking to for several years now. I gather that it’s described in The Artist’s Way but I confess that I haven’t read it! The idea (to me) is pretty simple. First thing in the morning, as soon as you get out of bed — after you’ve made a coffee, of course; there are greater priorities in life than writing! — you sit down and write about whatever’s in your head. The goal is to write about 3 sheets of A4 paper, which is long enough to tease out the things that are really bothering you, but short enough that it can be completed in the time it takes to drink your first coffee of the day. Before discovering Day One, I’d been using a web app for this purpose, called 750 Words. I’m happy with his reasoning that 3 pages is about equal to 750 words, so that’s what I aim for each day, though I don’t give myself a hard time if I stray too far from the target any longer. That’s another welcome feature in version 2.0 of the Mac app which has been in the iOS version for a while: it now displays a word count in the metadata bar at the bottom. Previously I had to save the entry, then look at its info menu to see the number of words I’d written that morning. Cue several rounds of hitting ‘Done’, checking my word count, then feeling obliged to edit & add more on a slow-brain day!

Using Pen and Paper

In the past, I’ve used other tools for my morning pages. For a long while, I was using pen and paper. I do rather like the pace of hand writing words. I’m slowed down enough by the pen that I can think more deeply than I tend to when I rattle characters off on the keyboard. I’ve a thing for stationery, too. I love Pilot G-Tec C4 pens which have a really thin — 0.4mm! — point:

New bio-polymer gel ink gives consistent inkflow. Ultrafine writing with no ink spread. Suitable for fax and NCR paper. Line width: 0.2mm.

Pilot G-Tec C4 Gel Microtip Rollerball 0.4 mm

They suit my — fairly dense, small — handwriting. When I’m in a more colourful mood, I adore the Staedtler fineliners:

Staedtler-Triplus Fineliner Pens: Multi. This water-based ink is in an ergonomic triangular shape pen for relaxed and easy writing. These pens can be left uncapped for days without drying up. This package contains ten pens with 0.3mm tips in assorted colors.

Staedtler Triplus Fineliner Pens

And I’m a fan of Moleskine notebooks, in particular, the cahier jotters:

Moleskine Notebooks, the journals that evolved from a legendary notebook. This version of the basic, yet classic ruled journal notebook is a stylish travel companion, perfect for writings, thoughts and passing notes.

Moleskine Ruled Cahier L - Red Cover

But handwriting has its downsides, too, mostly in terms of recall. It’s not always easy to discover things I’ve written about before when I want to find them again. (In fact, I’ve got a stack of notebooks that I’d like to have typed up, if anyone fancies a wee job!)

Using Evernote

I’ve also used Evernote for journalling. It’s not bad. It didn’t support Markdown, which didn’t stop me writing that way, it just meant that my notes weren’t as well formatted as they could have been. I’ve found it to be a pain to get notes out of Evernote en masse, too. But the biggest thing that bothered me about using it for my own writing is that I like using it as a filing system for other people’s material. I dump all the bits of paper I get (bank statements, utility bills, company correspondence, letters from my doctor, etc) into there, and I don’t really like mixing the stuff that originated in my head with the stuff that comes from other people. I like keeping them in separate silos. I’m sure I’m missing a trick around intelligently finding relationships between bits of content in each silo, but I’ll live with that for now.

Status Updates

The other thing I use Day One for regularly is to keep track of what I’m up to right now. I’m not always good at keeping notes as I do things, and I’m terrible at remembering specifically what I’ve accomplished during the day when I come to note down my achievements in iDoneThis. (You know when you ask a six year old, “So, what did you do in school today?” and they universally answer, "I can’t remember!”? Well I never grew out of that.) Day One has this delightful feature called reminders. On the Mac, you can have it pop up an alert at certain intervals during the day, where it’ll allow you to dash down a quick entry straight from the menu bar, then get back on with what you were doing. I’ve got it set up to prompt me for an entry every hour of the working day. When it pops up, I note down what I’ve been up to over the past hour, save it, then carry on. It’s a great way to have a short checkpoint, to reflect on what you’ve been up to, make sure you’re not getting sidetracked, and to note down the things that you’ll inevitably forget in a few hours.

All sorts of content winds up in there from these entries. Sometimes it’ll just be a few words on what I’ve been doing. Other times, it’ll turn into a longer brain dump when I’ve been researching something. Quite often, I’ll copy and paste a complex command line, or some subtle SQL I’ve been hand crafting, just in case it comes in handy again in future. It beats grepping my zsh history to find it again!

Feature Requests

So how’s the future looking for me and Day One? It’s pretty rosy. Put it this way, the new version was a paid upgrade (£18 for the pair of them) and it was an instabuy this morning, as soon as I saw the tweet that it had been released. It’s an app that’s a core part of my daily life, and I’m delighted to be able to support further development by buying the new version. I’m quite excited by what the future might bring, too, particularly with multiple journals and the app having its own synchronisation service. I’m really hoping that they’ll open up an API to third party tools, so I can post journal entries from other apps, and have other (web) apps consume the entries I create here. (In the past, I’ve mucked around with IFTTT, Dropbox, and a command line tool to get entries into Day One as a result of events happening on other web apps, but it was a bit… flaky.)

I’d love for the text search to become more intelligent. Right now, it will search based on words, and it’ll return all entries that contain the matching word(s), ordered by recency. I want a proper search engine for my 2,848 entries — something that’ll rank the results, and allow me to construct more complex searches. Saved searches would be handy, too. Another thing a 'proper’ search engine would enable is automatically surfacing related content using some sort of semantic analysis. This would allow me to discover old entries that are related to what I’m currently writing.

I did really like 750 Words’ semantic analysis, where it would give you some insight into how you were thinking or feeling, based on the content of what you’d written. I guess that’s pretty specific to my use case, so I’m not sure it would suit the core Day One apps. But if there’s a third party API to read journals, then somebody else could implement it, right? 😀

Download them today

All in all, I’m very happy with Day One, and I’ll be continuing to use it to capture my daily ramblings for the foreseeable future. The next trick is to try and get me to share more of those ramblings, instead of talking into the echo chamber! How about you give Day One for iOS and its companion Day One for Mac a shot today? I’d love to hear how you get along with it!


  1. I have to confess I’m not terribly good at tagging things. It’s difficult to predict how you’ll want to find something ahead of time. I’d rather just rely on good full-text search. 

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