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Simplification with Obsidian

Over the last 5 years, I have used Obsidian to journal, track projects and practice my writing. Here is what I've learned


I spent 16 years in school and I have been a notoriously bad note taker. Each year, I would buy a new 5 subject notebook, dig deep and proclaim that this would finally be the year that I would overcome my shortcomings and finally become the note taker that was needed to pass my classes. I would have highlights, tabs, a table of contents, and outlines so clean that chalk outlines at murder scenes would be jealous. And, each year, I would eventually find all 5 subjects flowing together, missing page numbers, incoherent bullet points, and eventually, it became more doodle than notes. I truly appreciated note-taking. Everyone from my classmates, to my dad, to my wife took exceptional notes and seemed to be able to recall any fact that was taught.

Simultaneously, I started to see the importance of journaling and how that could help one reflect and grow. I once again had the notebook, and the role models to journal well, but I still could not make the habit stick. Clearly, there was something intrinsically difficult in me that would just make it impossible to ever learn how to do either of these well, and for the first few years of my professional life, I just accepted that was the case.

One unassuming day, I had a co-worker share a link to a repo that was a note taking platform. It could help organize different notes, was available at any time on your machine, and created these beautiful linked graphs that looked like a sprawling network of brain cells. I was in awe, and the words that people kept using around it like “second brain” intrigued me. Later that day, I tried out Obsidian for the first time and I haven’t looked back.

5 Years down the line, I am still not a particularly good note-taker, or journaler, but I have finally been able to make a habit of both. So what changed? What makes some dummy simple offline markdown editor so damn special? What dark magic made a kid who couldn’t keep a bullet point list to save his life suddenly turn a corner? What were the 3 easy steps to follow to make such a hail Mary a possibility?

This makes me a terrible listicle writer, but there really isn’t a simple 3 steps to do. And in all honesty, it wasn’t something that happened overnight. The process did take 5 years to develop, and it will probably continue to change and evolve as time goes on. And therein lies the key. Own your process and develop your tools. I consider myself a maker. I enjoy the process of making something from nothing and solving hundreds of teeny little problems to overcome some challenge. My brain thrives when it is challenged to create. It turns into a cuckoo clock the minute you ask it to complete a repetitive, simple task. I took this realization into how I created my Obsidian vault. How could I make my notes a part of a larger system? One that I create?

In short, Templates. In long, templates and some additional plugins. Since blank text documents made my brain seize up, I could use templates to pre-populate headers, metadata, and prompts to initiate the flow of information. Obsidian’s daily notes are a great place to start with templates. My daily notes have changed over the years, but at this point in time consist of the following: • Links to the next/previous days • Habit tracking • A scratchpad for the day’s consciousness stream • Prompts to engage in reflection.

The daily notes are a place for me to just write everything down. This can be a Youtube video that I may have enjoyed, a response to how something made me feel, or just reminding myself that I took the trash out. Daily notes are my launching point, and if something is on my mind that exceeds the needs of temporal notetaking, I can put it in a Project.

Next to daily notes and my ideas folder, Projects are my next largest folder of notes. A project consists of a hub page to track any new pages created for that project, a kanban board, and any documentation that may be created for it. Recording and tracking projects this way has not helped to increase how many projects I actually complete. In fact, I don’t know of more than 2 or 3 projects that I have documented that are actually completed. That would be something I would like to revisit, but the note taking helps make the project into a story, and easier to pick up later if I move on. I love my projects, but I have found that taking too many notes counterintuitively makes me work on them less. I think if I write down everything that I plan on doing, I accidentally trigger my brain to think that I actually did the thing. At that point, it loses interest and I usually end up leaving a nice plan of attack in the pile of discarded projects. Since I figured this out, I have tried to not document projects as much, and instead try to work on something, then record what I did afterwards.

My Project hub template is the same as I use for my general thoughts hub. Using the Dataview plugin, I can generate a list of all files in a given folder. This does 2 things: It helps keep everything linked and organized, and gives me a single place to navigate a given area. My goal was to have a recursive table of contents. Before using the dataview solution, I was manually adding the pages to the hub, and I HATED it. Most hubs were nearly empty because the manual effort was mentally exhausting, as that kind of task was something I would likely only do if I was drunk, high, or both. Being able to automate that gave me a kind of organization that I never had before in any note taking system before or since.

Hub Notes, Dailies, and templates make up the main systems that I utilize to make Obsidian work for me. In future posts, I want to talk more about how I use Obsidian for work, then go into the philosophy behind making your own infrastructure: How a world full of curated, out of the box solutions accidentally ruined the simple joy of developing your own systems. I’ve linked the templates, as well as the list of plugins I used to utilize them, but I really would encourage anyone looking to give Obsidian a try to build their own. As I stated in the first line, I am a notoriously bad notetaker, and I have full confidence that you would create a better system of templates. It would also be better to go into Obsidian and slowly iterate and develop a workflow that suites YOU and what YOU want to get out of a digital note taking app.

For futher exploration, I HIGHLY recommend Dann Berg and his youtube channel and newsletter. His work inspired me earlier this year to revamp my Obsidian environment. His insights and work have been such a joy yo have in my feed.

This entry also acts as the first in my series about de-platforming your life: How to remove the stickiness of failing modern technology in favor of better, more human solutions. The title is a work in progress, but I have been wanting to write about this subject for MONTHS. With the recent news cycle talking once again about how shitty Meta, Twitter, Bambu, Sonos, ETC ETC ETC (OMG when will it stop…) have become, this seems like the right time to finally talk about it.

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