My Obsidian Experiment

From Listicles to Linked Ideas

The Starting Point

I recently decided to dive deep into Obsidian, focusing specifically on one use case: book notes. After reviewing various possibilities, I kept coming back to the question of how to transform reading into lasting knowledge. To get started, I returned to Nick Milo’s “Linking Your Thinking” channel—the same source where I first learned Obsidian basics in fifteen minutes. This time, I needed a refresher on the fundamentals, particularly the concept of connecting ideas across notes rather than grouping them all together in one giant note.

The Mental Shift

Here’s the challenge: My brain loves lists. For years, I’ve organized thoughts in linear formations (bullet points, numbered lists, etc.). That’s what order looks like to me. Obsidian’s graph view, with its constellation of interconnected nodes, fascinates me, but it also feels mentally cluttered right now. I’m struggling to envision how I might make the connection between a note about one idea and something I write six months later, or how to organize thoughts that seem to branch infinitely.

The mechanics are coming together. I’ve downloaded Obsidian locally and learned Markdown formatting—discovering that typing asterisks for bold or dashes for lists feels surprisingly logical once you abandon the toolbar mentality. But the philosophy remains slippery. When every note could link to countless others, how do you maintain coherence without chaos?

The Test Case

I’ve chosen my first test case: Mao’s Great Famine, a history book sitting in my Kindle library that I’ve started and abandoned more times than I would like to admit. The grades I received in my history classes weren’t terrible, but I would hardly call the subject my strong suit. Despite having an excellent history teacher in high school whose tests were only made up of essay questions rather than multiple choice, I relied on brute-force memorization. The information never stuck because I never truly integrated it.

This time, I’m approaching it differently. Instead of recording facts for regurgitation, I’m thinking in terms of tags and categories—people, dates, events, locations—but with a twist. I want to push myself to make personal connections, even when they seem tangential. If a historical event reminds me of a modern experience, that link goes in the note. The goal isn’t to write a school report; it’s to weave the material into my existing mental framework.

The Anticipated Struggle

I expect confusion. When I actually start reading, I’ll likely face that old impulse to transcribe everything important—which, historically, has meant nearly everything. Learning to curate rather than copy will be uncomfortable, and so will breaking the habit of hierarchical organization in favor of associative thinking.

But that’s precisely why I’m conducting this experiment to begin with. I’ve always admired people who can recall historical timelines with ease, and I’ve accepted that my current methods aren’t serving me. There is room to grow here, even if the path feels messy at the start.

What Comes Next

Once I begin reading, I’ll be documenting the specific process—what deserves a note, what warrants a link, and how the graph view actually functions when populated with real content rather than theoretical possibilities. Will the visual network reveal patterns I would normally miss in a traditional outline? Or will it confirm my fears about digital clutter?

There’s only one way to find out. I’ll keep you posted on what emerges from the chaos.