Writing and Reflecting in Obsidian — From Evernote

In Search of a Better Journal

This is part 2 of a series about how I write and reflect using Obsidian, an extensible digital note-taking interface with some surprising and unexpectedly useful features. This post reviews my history with journaling and digital note-taking tools, accounting for how I arrived at Obsidian from my first digital database, Evernote. I’ve been using Obsidian since 2021-02-06, and it has completely revolutionized my writing process. New posts every Wednesday until the series is complete.

How to Record Everything?

I haven’t always been so interested in writing everything down, but I have always had an interest in writing something down. When I was in college, I needed a notebook primarily to keep up with assignments and follow classroom discussions. (It was an entirely discussion-based curriculum, and the rules of decorum meant that if you didn’t have a way to keep track of what was said and what you wanted to say, you may never end up participating at all.) This was back when I was an aspiring musician as well, so I soon found myself relying on a pocket-sized Moleskine notebook I carried with me wherever I went so I could parse out song lyrics, doodle when I was bored in school, and write down assignment deadlines.

When I got an iPod Touch, sometime in 2008 or 2009, I installed Evernote, sold on the idea that I would be able to store—and recall—well, everything. That was the promise of the Information Age, wasn’t it? To leverage the awesome storage and computing power of technology to record and interpret data about our world in ways never before thought possible?

If only it were that simple! The truth is, I wouldn’t find a true solution to this problem until Obsidian, but I want to share the process it took me to get there. There are a lot of great apps out there—a lot of great note-taking solutions in general—and everyone’s needs are different. What didn’t work for me might work for you, and what works for me may not be a perfect fit for your own needs.

Going Digital

For five years, I used Evernote almost exclusively as a catch-all for everything digital. When I started writing a novel in 2010, I returned to my analog roots with a new hybrid system: Evernote Smart Notebooks. The premise was simple: I could write in the notebook, scan the pages into Evernote with my iPhone, and it would use Optical Character Recognition (OCR) to search my handwritten notes or find them by tag. The Smart Notebook system even had neat little stickers that would automatically file the notes according to certain predetermined tags.

I had organized Evernote according to these Getting Things Done (GTD) principles as best I could, but it was still pretty unwieldy. While Evernote wanted to offer tasks, events, notes, and image storage all in one place, it was starting to become bloated and slow trying to process everything, and I found myself moving toward more specialized tools.

Day One, for instance, offered a much better journaling interface. It could identify photos taken from the same day as a given journal entry and present additional context by showing me what else I had been journaling about “on this day” in my own personal history. There were plugins that would let me automatically import tweets, facebook posts, and my Instagram feed, making it feel like a comprehensive look at my cross-platform journaling. Plus, once I transcribed all of my old college notebooks, I was able to print out a collection of bound softcover volumes to put all of my disparate thoughts within arm’s reach.

Scrivener was similarly much better suited to long-form writing and project management than Evernote. When I was searching for a scene or a chapter, I knew I was just getting my fiction writing, rather than having to wait for the search to index every single note I had ever uploaded. Ulysses offered an even more streamlined writing environment, opening my eyes to the power and versatility of Markdown.

Then, for task management, nothing (to this day!) can hold a candle to Things. I got a free license for it through my work, and it revolutionized the way I approached project management for everything from personal grooming to my professional aspirations.

While I had started with one app to rule them all, it undermined its own functionality by spreading itself too thin. As my primary work computer transferred from a MacBook to an iPad, I started to get bogged down with long loading times and insufficient search results. Plus, you can see the problem, right?

Too many things!

At the peak of this fragmentation, I was writing in four different notebooks for my disparate writing projects, then manually transcribing notes (or whole chapters) into four or five different apps on my iPad. Evernote was still pretty good for storage, but it slowed to a crawl when it came to retrieval, and I had so many things in so many different places that I wasn’t even sure where to search for them anymore!

Around 2014, I also started investing my time more heavily into journaling as a regular way to hone my writing practice and keep putting words on a page. The thing that kept surprising me about just a simple pen and notebook was how fast it was to just open to an empty page and write something down. As advanced as all of my technology was, it couldn’t compare to the speed of analog writing, which didn’t require electricity or loading time to use.

I found that I was losing my train of thought watching progress bars try to load the material I was working on. I wanted something simpler, more straightforward, with that same sense of immediacy.

Bullet Journaling

In 2017, a friend showed me her Leuchtturm 1917 journal and I was struck by a marvelously simple, yet life-changing innovation it implemented that I had never seen in any of my Moleskine notebooks—it had page numbers. This simple feature that anyone might take for granted blew my freakin’ mind. I had never considered creating an index that could refer to different sets of writing within a single notebook, which, in turn, led to the creation of a Master Journal Index that could refer to different threads of thought throughout multiple volumes of my journal.

Soon after, I discovered the Bullet Journal Method which offered a solution to nearly everything that was bothering me. Its principles of indexing, rapid logging, manual migration, and regular reflection took me out of the loading screen purgatory of all my apps and gave me one notebook to rule them all.

Of course, I wanted a digital analogue. It wasn’t enough to get all of my paperwork under one cover, I wanted to take the same principles of bullet journaling and apply them to my digital tools as well. Paper, after all, is fallible. I never got over losing that Field Notes notebook, and although I had an analog solution for my note-taking needs, I needed to transcribe all those notes to have them back up to the cloud and resurface in Day One’s “on this day.”

Drafts: Almost Perfect, but Not Quite

A plaintext quick-entry text editor for iPhone, iPad, and Mac, Drafts seemed to be the answer to my prayers. It opened with the speed of a Post-It note, supported Markdown (which I was coming to love,) and was able to send whatever text I gave it into any app that ran on my phone.

Drafts actions are configurable (with a Pro subscription,) so I set about the task of copying and pasting my way to a robust set of actions that allowed me to approximate my Bullet Journaling practice within my digital ecosystem. I created a Bullet Journaling action group that let me capture notes, events, and tasks all within Drafts, then press a single button at the end of the day to send them on their merry way to their respective apps, which I had whittled down to Day One, Things, and Fantastical, a spectacular calendar app. My long-form writing still lived in Ulysses, where I could use x-callback-urls to reference my works-in-progress from Things or Day One as needed.

But, as easy as it was to input all of my data, I still didn’t have a good way to find everything once it was there. I needed the equivalent of a Master Journal Index for my computer that could look at all of my journal entries, all of my fiction and nonfiction writing, and all of my assorted associated research notes at once, along with the ability to cross-reference them with as little friction as possible.

All Roads Lead to Roam Obsidian

As I mentioned in my last post, I thought I had found the perfect solution in Roam Research, but I was mistaken. I needed that offline simplicity, that lightning-fast loading time, and that extensibility that would enable me to refine the tool over time to serve my changing needs. Obsidian knocks it out of the park, delivering everything I could ever want from a digital note-taking input, storage, and retrieval system, and every time I wish for something it can’t do, the developers introduce the very feature I was looking for, and it works even better than I had imagined it would.

Next Steps

In the next post, I’ll go into some more detail about how I synthesize my digital and analog notes for both my Morning Pages and my regular journaling habit, as well as explore the tools and plugins I use to make it happen.