Making Obsidian Work Like Me

Why I’m recommitting to a new note-taking system, and what I learned from my first efforts at customization

After a lot of consideration of PKM options, I’ve landed on Obsidian because it really is the only tool that can meet all my requirements. But the reason it can meet those requirements is because it is so wildly customizable—and all that customization will take a lot of work, drawing on a combination of community plugins, templating tools, dataviews (a plugin that lets you create complex and filtered views of your notes), python scripting, and AI support (and I am sure, many other customization options I haven’t found yet!)

I am really glad that I started the tweaking and customization process with a very small Obsidian vault: About 450 notes that I either created manually this summer, imported as screenshots or imported from exports of my ChatGPT history. When I broke, mis-tagged, erased and messed these up, it wasn’t a huge deal to fix it. I am going to get my filing system and workflow more stable and less error-prone before I import my Evernote archive.

Is all this customization worthwhile? Yes, I think it is: That’s what inspired

my newsletter about meta-work.⁠

⁠

About this draft

The draft below was drafted by

Claude.ai⁠

from my notes. See

Using AI with and about Obsidian⁠

for context on how it was created, including details on how I plan to use Obsidian to make this kind of AI-assisted work easier. Unlike my usual practice, I’m not really editing this draft, though I have annotated slightly to add additional information and some comments on the AI writing.

The process I describe in this post unfolded over a day and a half, following two months of using Obsidian without doing much to tweak it.

Making Obsidian Work Like Me

I'll admit it: I'm a tech tool junkie. Over the years, I've amassed quite the collection of apps and platforms to manage my work and thoughts. As I recently told a friend [”a friend”!! was my custom GPT], "I'm using a mix of Evernote, Coda, Scrivener, Zotero, ChatGPT/Claude, Skitch/XSnapper, and Obsidian/Tana. Each has its strengths, but the lack of integration and poor search functionality across tools is causing friction."

Sound familiar? If you're anything like me, you've probably found yourself drowning in a sea of digital tools, each promising to be the ultimate solution for personal knowledge management (PKM). But as our digital lives grow more complex, so do our needs. [This is the kind of generic writing that gives me hope I still have a future as a human writer.] And that's how I found myself diving headfirst into the world of Obsidian.

Why Obsidian? Well, I was drawn to its promise of connective, mind-mapping power. But I quickly discovered that making Obsidian truly work for me would be a journey - one filled with frustrations, "aha" moments, and a whole lot of Python scripting.

The Challenges

Let's start with the elephant in the room: tool overload. "The struggle to find information across these platforms is huge," I realized. "Coda's search is lacking, my Super Coda setup [using a Coda pack I wrote to create a directory of all my Coda docs] doesn't quite do the job, and Evernote is becoming increasingly cluttered."

Then there's the complexity factor. While I craved the connective power of tools like Obsidian and Roam, their learning curve often felt like scaling Everest. And don't even get me started on the state of my Evernote - "I'm feeling overwhelmed by the disorganized state of my Evernote, the difficulty in managing everything, and the potential loss of serendipity that comes from having a well-organized system."

The Journey

My Obsidian adventure began with a classic tech blunder: insufficient backups. As I ruefully noted later, "I should have backed up better before starting my experiments! Sync isn't backup and Obsidian is complicated that way." Learn from my mistakes, folks - always, always back up before diving into a new system. [Luckily I had zipped my Obsidian vault two days before, when I was ready to give up and go back to Evernote. That zip file is what I reverted to after my efforts to recommit to Obsidian, including Python cleanup, effectively nuked a lot of my files.]

As I started to customize Obsidian, I encountered a whole new set of challenges. YAML formatting issues, tag duplication, and the mysterious workings of the File Organizer plugin all tested my patience. "File Organizer isn't really working," I grumbled at one point. "It keeps saying 'Can't read properties undefined (reading replace)'." [This turned out to be a result of me forgetting to re-launch the local server I set up to power the File Organizer plugin. Learning to setup a local server was another step in the process that would have been beyond me without the help of GPT, but it wasn’t that hard...just something I will need to automate so that I don’t have to remember to relaunch the sever every time my computer reboots.]

But with every frustration came an opportunity to learn and improve. I dove into Python scripting, creating custom solutions for everything from tag cleaning to file comparison. I experimented with plugins like Tag Wrangler and Smart Connections, though the latter required setting up a local server - a process that came with its own set of challenges. [See

Script Descriptions⁠

for the many scripts I have already created.]

The Lessons

So, what have I learned from this Obsidian odyssey?

Automation is your friend, but it's not infallible. Custom scripts can save you hours of manual work, but they need constant tweaking and oversight.

Consistent metadata and tagging practices are crucial. A well-structured YAML frontmatter can make all the difference in organizing and retrieving your notes.

The perfect system doesn't exist - but a good-enough system that you actually use is infinitely better than a theoretically perfect one that you abandon.

Don't underestimate the time investment. Setting up and optimizing Obsidian for personal use is a significant undertaking, but the payoff in improved organization and retrieval can be immense.

Always, always back up your data before making major changes. I can't stress this enough!

The Road Ahead

Am I done customizing Obsidian? Not by a long shot. I'm still grappling with automating my Smart Connections server startup, fine-tuning my file organization system, and dreaming up new Python scripts to streamline my workflow.

But here's the thing: for the first time in years, I feel like I'm building a PKM system that truly works like me - not the other way around. It's a work in progress, sure, but isn't that what personal knowledge management is all about?

So if you're feeling overwhelmed by your digital tools, remember: the perfect system is the one that works for you. And sometimes, building that system means rolling up your sleeves, diving into some code, and making the tools bend to your will. It's not always easy, but trust me - it's worth it.

For more, read

The Nerdy Details⁠

, including

Script Descriptions⁠

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