Once More to the Digital Journal

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There are some things for which I cannot make up my mind. Since 2017, I’ve been writing about my paper journals. I’ve generally kept a journal (or diary, or notebook) since I was 24 years old. The vast majority of this has been on paper. There have been gaps, but this blog has served to fill many of those gaps. After a long gap, in 2017 I came across an article about Henry David Thoreau’s journals, and I wrote about that. In a comment to that post, a reader pointed me to an article on the journals of John Gaad and that was eye-opening to me. Almost at once, I started a paper journal again and have kept that up more or less these last 4+ years, filling nearly nine large Moleskine Art Collection sketchbooks. I love the tactile feeling of the notebook, the paper, and I enjoy writing with my fountain pen.

A stack of my paper journals

There have been small gaps along the way even here. Almost a year ago, for instance, I decided to try keeping my journal in Obsidian. That lasted a few weeks before the guilt of not writing my journals on paper began to creep back in. I went back to my paper journal, until later in the year when I decided that, for practical reasons, I should go back to a digital format. That too didn’t last very long before I was back on paper.

Recently, I’ve found myself skipping my journal entries quite a bit because I am too tired to write them out. I have a lot to say, but it takes me a long time to scribble my thoughts out on paper. I missed journal entries for the last 2 weeks of our vacation, for instance. Not writing in my journal is worse than any medium on which I decide to keep it. So I am once more heading back to the digital journal format, flipping and flopping like a politician.

This time, I’m trying to make a better effort. I recently wrote about how I’ve changed my daily notes, using a single file instead of a separate file for each day. These daily notes (captured in a text file in Obsidian) capture the factual part of my day. Often my journal entries were just a reprise of the facts of the day as well. I thought that since I had my daily notes for the facts, I could use my journal for thoughts and introspection related (or not) to those facts. Factual journal entries are quick and easy, but thoughtful, introspective entries require more effort, both mental and physical. Try as I might, I wasn’t up to the task of handwriting these entires and I was losing them because of that.

That is when I decided (back on January 10) to switch to keeping my journal in Obsidian again. This time, however, I am doing it as a deliberate experiment, and I have a goal: keep my journal in digital form in Obsidian for the remainder of 2022. At the beginning of 2023, I’ll review how things went, good and bad, and decide if I want to continue with this format or switch back to my paper journals.

There are some advantages to this:

  1. Because I preface each entry with an index number, I can refer to journal entries easily in Obsidian using links. My daily notes file can therefore takeover as a chronological index to my journal. Previously, I’ve done this indexing on paper.
  2. The journal is easier to search, though my need to search it is not that frequent.
  3. I can type fast and without much effort, unlike handwriting which is slow–much slower than I think–and tiring, so I have the potential of capturing more of those thoughtful, introspective entries.
  4. I’m committing a year and can reconsider after that, but since I’ve given paper journals many years experimentation, it seems only fair that I try this method for longer than a few weeks.
  5. If I decide that digital works for me after a year, I can still have my cake and eat it, too. There are services like Lulu that allows one to create books and I can create annual printed volumes of my journals to sit on a shelf with my existing ones if I want to.

One thing I’ll want to look at a year from now is not only if I was successful in keeping the journal in Obsidian for a year, but also was I successful in being more thoughtful and introspective. It will be particularly interesting to see how my new daily notes format (about which I’ll have much more to say in Episode 16 of my Practically Paperless with Obsidian series) combined with my journal text file capture a picture of what goes on in my life.

I thought about just switching without making an announcement like this one, but I felt it would be dishonest for me not to admit this change. If nothing else, it shows that there are some things that are complex enough to me that I can’t readily make up my mind. I’ve failed at this before. This isn’t necessarily a bad thing. I think real experimentation is key to making a final decision on this.

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  1. Did you ever think of using Day One for journaling? I know Patrick Rhone has used it to produce print volumes, but he uses Day One differently from most folks. I also saw a DayOne to Obsidian script online somewhere.

    Like you, I’ve been using paper for a long time but have been thinking of making the switch as long as I can get a print version at the end of the year or half year.

    1. Harvey, I actually subscribed to Day One for a year, but hardly used it at the time because I was set on sticking to paper. At this point, I’m trying to do all of my writing in Obsidian so I will stick with that for the year and evaluate things at the end. It shouldn’t be hard to produce a printed volume from either markdown or a PDF using a service like Lulu, if I end up going that route. One thing will be size: in the first 10 days I’ve been doing this, the PDF export is 7 pages long; 365/10 = 36.5 * 7 = 255 pages of PDF for a full year. I’m not sure what that would translate to in a printed volume, but I’ll report back on that in a year. 🙂

      BTW, I love Patrick’s blog — I’m always happy when new posts appear.

  2. Per your request…..”Good grief!”

    But seriously, I’m one to talk. I took a break from uploading all my various task lists from Field Notes/Bullet Journal back into Workflowy as we speak. Not 3 weeks ago I said I was all paper!!!! Pot…meet kettle.

    Let us know how it goes!

    1. Malanie, next week’s Practically Paperless post is about my new method for managing my daily notes in Obsidian. One of the side-effects of this new method is that it provides a way for me to capture the “important” notes I scribble in my Field Notes notebook as part of my daily notes. For me, it works out to be a good hybrid: I continue to use my Field Notes as always, but now have a process for capturing the notes I want to keep and be searchable. So far, I think this is a good balance.

  3. Hi Jamie, I have been following your diary journey for a while now and have gone through a similar process myself. What I settled on was using Obsidian as the “canonical” location for all journal entries. But most days I write on my iPad using the Apple Pencil and Good Notes app, which I then convert to text and import into Obsidian. I prefer hand writing this way but some days it’s just not possible and I resort to using my phone to type an entry. It would drive me crazy to have entries in more than one place but seeing as they all end up in Obsidian it’s fine. Now I am going through the process of adding all my old paper notebooks to Obsidian using Google Lens (on the Google app for iPhone) to convert them to text. Maybe this hybrid model would work for you?

    1. James, I like your process. What I have found is that I prefer handwriting to typing, but I do it so much more slowly that I am apt to write very little, and I feel like I miss out on the details I capture because of it. So even if I used my iPad with an Apple Pencil, I’d run into the same issue of just not writing quickly enough to capture everything I want to capture. I completely believe in the technological side of it. I just don’t have the patience to write at length longhand, which is what I want to be able to do in my journal. Typing eliminates that problem–at least so far.

  4. Jamie, are you keeping your journal in the same single file that you are now using for your daily notes or are you using a separate file for journal and then one for daily notes?

    1. I am keeping it in a separate file, one file per year of journal. But because since 2017 I have given each entry a unique index number (including in my paper journals), I continue to do that in the journal file as an “H2” heading. This makes it easy to link to a particular journal entry from my daily notes file, which of course, makes the daily notes even more useless as in index to my life.

      I’ve got more about this coming in the next Practically Paperless post on January 25.

  5. I feel this so much! Since I know myself and know that I’ll never decide on one or the other “for good”, I’ve resigned to using both paper and digital journals. I use Org mode for digital, and the big A4 Moleskine “Art” for paper. To alleviate some of the guilt of using digital, I’ll often print a day’s entry, cut it out to size, and glue it into the paper journal. Sometime’s I add some (hand-written) additional commentary. It feels a little too much like “scrapbooking”, but ¯_(ツ)_/¯. I still also print each month from the Org journal and add it to a 3-ring binder, just to have a “real” copy. I don’t know if it’s the best of both worlds, but it works.

      1. Tron, it turns out that despite being a much faster typer than I am handwriter, my journals are on paper for the foreseeable future. The main reason: I lose all consistency when I try and write them in digital form. I just can’t keep at it. But I have no problem flipping a notebook open in the morning and scribbling away when I get back from my early morning walks. I do index my journals in Obsidian. Every entry in my handwritten journals have always gotten a number. I have a note file with date headers and then a list of entry numbers and titles for that day. I write my title in the notebook with an eye toward searchability so that searching my index file almost always points me to the entries I’m looking for. Then it’s just a matter of flipping to that entry in the proper notebook.


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