The Missing Journaling Workflow

Of the difficulty to drop Day One

When I first heard of my Day One becoming a subscription service I – once again – started to reconsider how I want to keep my journal.

I’ve been using Day One for years and I’m really grateful for who they made regular journaling work for me. It’s hard to argue that whatever kind of journal system one employs: it’s worthless if you don’t actually use it.

I get the fact that Bloom Inc, the company that develops Day One, needs constant revenue to expand and improve their product. But here’s the thing: I don’t want more features being stuffed into the app. I was totally happy with Day One syncing via iCloud or Dropbox. I’m sure a huge effort and thus money goes into running their own sync service, while previously just relying on iCloud and/or Dropbox. While I understand that Bloom needs their own infrastructure to make some happen that probably weren’t possible otherwise I hate the fact that I have to rely on their Servers running to keep my diary in sync. They could pull the plug any time. They could decide to charge whatever amount of money from me to keep my Journals in sync.

Call me old fashioned, but I don’t like having subscriptions for more and more parts of my life. I really love the idea of paying a fair price up front for a good product and then own that product. At least for the mount of time it works on their current respective platforms. Thingsist a great example for that: It comes at an unusual high price tag for a todo app. But it’s well worth it and I can be sure to run it for some time. Synchronization would keep on working even it (beware!) Cultured Code went out of business, at least until the next API changes in CloudKit, that is.

But back to my dilemma with Journaling. After finally introducing the long promised end-to-end encryption Day One is, without a doubt, the most convenient and beautiful way to digitally write a journal.

But, the more I think about the issue the more I realize that portability and open formats are more important than convenience. There simply should be no barriers to access your writing in years and decades to come. The best way to attain future-proofness is, who would have guessed, plain text files. Add markdown to the mix for some nice formatting and the possibility to link images.

A Perfect Journaling Workflow

Here’s how I imagine the perfect way for keeping a digital diary.

File Structure & Sync

  • All entries are stored in plain text files
  • All files can be put in a cloud storage of your choice (WebDav/OwnCloud, iCloud, Dropbox, Google Drive), Bonus points if this was somehow conveniently possible through git (eG auto commit and push at the end of each day and/or on press of a button)
  • Markdown is used for formatting
  • A mobile app allows to easily copy photos to an appropriate location on the file system/cloud storage of choice and reference it with markdown

I’m still undecided if I prefer having a single file per event, day, week, month or year. I tend to having year-based folders and within those a file for each day, named with a simple date stamp. Photos follow the same format (optionally with a time stamp or an incrementing number if there are more than one per day):



I’m not sure If there’s a reasonable way to encrypt all entries while, at the same time, making it possible to access them from all sorts of software on various devices and operating systems. I’d love to get to know about methods of doing this, though.

Bonus: Viewing, Browsing & Re-living Memories

It would be nice to have an apps that presents your journal beautifully, making it searchable and shows you previous year’s entires on any given day.

But as we’re using markdown files it’s also possible to make use of a static site generator such as Jekyll or a flat file based CMS like Kirby to build a nice web page of one’s journal.

Current State

I’m still using Day One and I don’t think I’m gonna leave it very soon. It looks like it’s still going to work for a while as I’m used to even without having to buy into their subscription modal. But to me it seems quite obvious that things are not going to stay like that forever.

Currently I’m experimenting with simply using iA Writer with the aforementioned structure of markdown files.

I’d love to hear other people’s approach to digital journaling.

Leave a Reply