I’ve kept a journal for most of my adult life. I got started in my early twenties filling dozens of blank journal books. Ten years ago, I went digital with an app called Day One, and I have been using an iPad to journal since then. My journal holds thousands of entries — over a million words — spanning more than thirty years of private thoughts and memories.

Day One is my most consistently used app for the past decade. The app provides a calming, distraction-free writing interface and an end-to-end encrypted syncing service that keeps my writing secure but available on all my devices. It handles photos beautifully, accepts audio and video entries, automatically captures metadata about your writing environment like location and weather, and links automatically with Instagram. Journal templates, writing prompts, and the “On This Day” personal history review round out an incredible journaling experience. I enjoyed it so much that I even took the time a few years ago to type in my old paper journals to have a complete digital record of my life’s musings.

And yet, I’ve had this nagging idea that I should give up on Day One and start using Craft as my daily journal software.

Why would I leave Day One?

On the surface, I’ve wondered if I needed anything more than a basic writing app for my journal. After all, I wrote for years and years with just pen and paper. Did I need a dedicated app with another paid subscription?

Yet, my true interest is more profound than saving money or mere simplification. It’s widely known that to write well; you have to read. There’s no better on-the-job training for an aspiring author than to read the works of other writers. It’s less commonly understood how many writers keep a private journal and, more importantly, how they leverage their private missives as inspiration for their published works. Henry David Thoreau, Joan Didion, and Susan Sontag were avid journalers who attributed at least part of their success to keeping a diary. David Sedaris and Joyce Carol Oates both consider their private journals to be critical parts of their writing process. Ralph Waldo Emerson filled nearly two hundred journal volumes over his lifetime, which he frequently consulted as source material for his essays and speeches. He spent months cataloging his journals to make access easier.

A reason I’ve maintained a journal for so many years stems from a deeply-held desire to become a published author. My earliest journal entries make this point again and again. When I root out the source of my few published pieces, each can be traced back to its origin in my journal.

As much as I love Day One, Craft has stolen my heart as an innovative note-taking and writing app that I’ve used for a little over a year as my knowledge management system. Modeled after Professor Luhmann’s Zettelkasten system, I use Craft to house about a thousand interconnected notes and insights from books I’ve read. The power of connecting reading notes through a system of links and backlinks is truly astonishing once you open your mind to the possibilities. I’ve shared how I use Craft to leverage what I read, and it’s this versatile linking capability that has drawn me to use it for my private journal.

What if, like Emerson, I took steps to make my journals easier to access when I’m writing for others? What if I brought together my journal writing and reading notes into the same cross-linked system? Would the organic connections I’ve discovered from my reading grow deeper through close association with thirty years of journals? Could swirling together my journal writing and book notes in a system like Craft make me a better, more productive writer?

Might the convenience of having all my writing in one place, fueled by the connecting power of links and backlinks, outweigh the benefits of a dedicated journaling app?

To answer these questions, I launched an experiment: I kept my daily journal in Craft for an entire month to see whether or not these private musings would infuse greater insights into my Zettelkasten system and, ultimately, better writing.

As part of the experiment, I imported 3,200 journal entries into Craft to test its search and linking capabilities (see the end of this post if you’re interested in learning how to export Day One to Craft). I initially expected to use Craft’s Daily Notes function but soon decided against that. The implementation of daily notes in Craft felt half-baked and disconnected from the central note-taking system. Instead, I created a “Journal” folder in the main Craft notes area, alongside my reading and permanent notes.

A Month of Journaling in Craft

Here’s what I learned after thirty consecutive days of journal writing in Craft:

Performance

I was concerned that Craft might lose its pep with several thousand journal entries spanning more than a million words added to its data banks, yet performance remained snappy. Search results were near-instantaneous, and syncing updates between the Mac and iPad were as fast as ever.

Security

Craft’s syncing system does not provide end-to-end encryption like Day One. I wasn’t very concerned about security or encryption for my reading notes. But my private journal? That’s a different story. In the end, I decided to accept the security risk for the promise of new insights and writing productivity garnered by a connected journal.

Writing Experience

I found the writing experience in Craft to be mostly pleasing. I hid the navigation sidebar with a keyboard command (CMD-) to provide a clean, distraction-free writing environment. Numbered lists, bullet lists, pictures, and even Apple Pencil drawings were easy to add. I enjoyed moving entire paragraphs around in my entry with just my index finger. But, there were some annoyances. Craft doesn’t permit a change to its default font or font size. I usually write in my journal before bed. In Day One, I scale up the font to make it easier on my tired eyes. In Craft, I found myself straining a bit when I wrote at the end of the day, wishing I could make that font a little easier to see. And while I generally don’t spend too much time editing my journal writing, I found Craft’s Undo capability tedious. While Day One will quickly erase an entire sentence with just a couple of CTL-Z commands, Craft insists on undoing each character, one by one, even to the point of redoing and undoing typos. It’s a small thing, but enough to pull me out of the writing trance when it happened, and something that more mature writing apps handle better. But, these are minor complaints. The overall writing experience in Craft was positive.

Search

With my journal now part of Craft, I could finally sift through decades of personal writing for insights to link to my knowledge system. Yet, I soon discovered that searching Craft with all those journal entries had limitations. Before this, a CMD-O search in Craft usually produced interesting and relevant results. Now with thousands of rambling journal entries thrown in, a search wasn’t as reliable or valuable. For instance, a CMD-O search in Craft for the word fatherhood produced a list of 30 randomly ordered documents. The same search in Day One found 65 entries, ordered properly by date. I learned Craft enforces a hard limit of 30 documents using this on-the-fly search method, though it’s unclear how it decides which to present. Craft’s dedicated search pane found all 65 fatherhood journal entries, but reviewing the search results was cumbersome. The journal entries were again presented in a random order, and the scroll bar persistently leaped back to the top of the list when I clicked on an entry, losing my place. This made a review of a long list of search results very challenging.

Further, Craft’s search functionality is ham-stringed by its reliance on text blocks. For example, If you search for a journal entry with the words fatherhood and marriage, Craft will only find documents where the words appear in the same paragraph. If the search words appear in different paragraphs of the same document, Craft won’t find it. Day One had no such limitation.

Dates

Dates are the universal building blocks of every journal. Since Craft is primarily a note-taking app, it doesn’t provide much context on the date something is added to the system. This can make finding entries for a particular day, week, or month more challenging. I partially solved this by appending the date to the journal entry’s title, so I can at least view the date as I scroll through a list of entries. But, there’s no easy way to zoom to a particular time period in Craft like you can with Day One.

Linking Struggles

Connecting thoughts through the power of two-way links was one of the main reasons I wanted to try Craft as a journaling tool. Surprisingly, I struggled to apply links when I journaled, and when I did, they served as a work-around to apply a tag vs. a legitimate link. This troubled me since creating these links comes so easily when I’m writing and curating reading notes. It seems my mental mode when I write in my journal doesn’t lend itself to self-editing or analytical reasoning. I must journal from a whole different side of my brain, favoring feelings, vague intuitions and dreams over links and connections and knowledge building. The writing fizzled any time I stopped to scan for potential links as I journaled. This happened again and again.

The Return to Day One

After a month of journal writing in Craft, I realized the truth. My journal isn’t meant to be poked or prodded, linked, or back-linked. For me, the act of writing every day in a journal is therapy; writing how I feel in the moment keeps me healthy and balanced. My attempt to elevate the process in Craft only diminished the meditative value of the journal writing, while producing little in the way of new connected insights. Not only that, but my system of carefully curated wisdom in Craft felt swamped by a tidal wave of mostly unremarkable and repeated personal observations, which obscured much more than it uncovered.

Before importing my journals, everything in Craft had been vetted and polished to contribute to my understanding of the world and what it means to be human. The source of these insights was gleaned from other writers’ books, but each note was carefully distilled and refined in a personal way that is meaningful to me. While my journals are comprised of all my own words and heart-felt reflections, they’re raw and meandering and filled with empty calories, which simply aren’t suitable for the wisdom I collect inside Craft.

So, my journaling experiment ended with a return to Day One, keeping Craft apart and sanctified as my knowledge system.

Back in Day One, I felt a new appreciation for the soft, cozy feeling the app offers the constant journaler: the writing prompt that stirs your imagination as you open the app; the time travel of reading your past “On This Day” entries that transports you back ten, twenty, even thirty years ago; the comfort and security of end to end encryption of my most private thoughts; the easy swiping through the past week’s entries to connect you to the story arc of your life; and maybe most important: that precious altered state you enter as you write for just yourself without any expectations or demands … but honesty.

This experiment may not have resulted in any new Emersonian journal insights, but it did ultimately lead me to a better way to leverage my journal writing in Craft. As part of my weekly review, I now take some quiet time with the analytical side of my brain to reread the previous week’s journal entries for insights and ideas that add something meaningful to my knowledge system in Craft. It’s the perfect way to maintain the therapy of my journal process while leveraging the best of my thinking in Craft. And since my lifetime of journal writing resides digitally in Day One, I’m just a couple clicks away from discovering those lost insights lurking inside this vault of my life’s experiences and musings.

Afterward: How to Export Day One to Craft

Here are the steps I took to export over 3,200 Day One journal entries and 700 embedded photos to Craft. I used the Bear and Hazel apps to help me in the process.

  1. In Day One, I used the “Export … JSON” function to export all journal entries.
  2. In Bear, I deleted any notes in the library, emptied the trash, and restarted the app.
  3. I imported the Day One JSON file into Bear.
  4. In Bear, I used the “Export as Markdown” function with “export attachments” checked. Craft limits each import of markdown notes to 2,000. To get the linked images to come across, you need to make sure your Bear export falls below this limit. In Bear, I selected about 1,500 entries and saved the export into an empty folder on the desktop. I called it Bear 1.
  5. I repeated the process for the next 1,500 entries and again for the remaining entries. Folders Bear 1, Bear 2, and Bear 3 were now populated with markdown text files and folders of images and PDFs.
  6. If my original Day One entry didn’t have a title, it used the first paragraph of the entry as its title in Craft, which was too long. I wanted to shorten that to a consistently formatted date. If it did have a title, I wanted to append a consistently formatted date to that title. I created a few simple rules in the excellent Hazel app to remedy this.
  7. In Craft, I imported the contents of the Bear 1 folder using the “Markdown files” option. This added the first batch of journal entries to a newly created folder called Bear 1 inside another newly created folder called Imported Notes. This is important: I waited until the process concluded, and Craft was done syncing. In my case, this took about 15 minutes with my slow internet connection. If you move the entries out of the import folder before the sync is completed, many of the images in your entries won’t sync.
  8. I repeated step #7 for Bear 2 and Bear 3 folders (this only applies if you have more than 2,000 entries in Day One). Again, I waited for each to fully sync before proceeding. I tested the sync on an iPad to see all the entries (and images) to confirm everything was working.
  9. I moved the entries out of the Bear 1-2-3 folders into a Journal folder at the highest level in Craft. To do this, I had to select all the entries and keep scrolling down to the bottom of the window repeatedly to make sure I got them all.
  10. For new entries written in Craft, I used the “/Date Today” keyboard command to append the current date to the end of the title to match the format used in the above Hazel rules.

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