Why I Keep Coming Back to Obsidian

I keep thinking about how we ended up scattering our thoughts across so many platforms that finding anything becomes its own kind of work. You write something down to preserve it, then spend more time hunting for it than you did thinking about it in the first place.

The chaos isn't random. Notion databases that promise organizational clarity but deliver administrative overhead. Apple Notes serving as digital pockets—perfect for quick capture, useless for deep retrieval. Desktop folders that multiply like digital kudzu, each one representing some optimistic future organization that never quite arrives. Each platform optimized for a different fantasy of how thinking actually works: linear, categorizable, immediately actionable. When the reality is messier, more recursive, more human.

I've been keeping notes for decades now, which sounds almost quaint in a time where every private thought gets marketed as content. But the act itself—capturing something worth returning to—remains essential, even as the infrastructure around it has become increasingly hostile to sustained reflection.

What drew me to Obsidian wasn't its features, though they do matter. It was something more fundamental — the recognition that my thoughts might actually belong to me. When I take notes, the files sit on my own machine, readable in any text editor, immune to the particular brand of digital feudalism that forces us to be tenants in our own intellectual spaces. This isn't nostalgia, but rather pragmatism about what it means to think in a world that treats attention as a commodity by default.

But ownership is just the foundation. The real magic happens when you stop organizing thoughts and start connecting them. When the system becomes less about filing and more about discovering what you didn't know you were thinking about. I'll write something about a book I'm reading, link it to a project I'm planning, and months later I’ll find threads I never consciously drew. The software doesn't do this for me — it just gets out of the way while I do it for myself.

There's a particular quality of attention that emerges from working this way. Let’s call it cognitive intimacy. The sense that your thinking actually has room to breathe, to contradict itself, to change direction without requiring justification to some imagined audience. My daily notes become conversation partners rather than just mere records. Ideas accumulate weight and complexity instead of disappearing into some sort of digital ether.

This isn't to say that other tools don't have their place. But I've learned to be more deliberate about what I ask of each platform. Notion excels at project management but makes contemplation feel too much like work. Apple Notes handles the ephemeral beautifully, but offers no path toward depth — at least not for me. Each tool embeds assumptions about what thinking should look like (to varying degrees), and those assumptions accumulate into habits we might not have chosen consciously.

The friction in Obsidian — the mild learning curve, the occasionally clunky mobile experience — feels honest in a way that frictionless interfaces often don't. It asks you to be intentional without being prescriptive, to develop your own patterns rather than adopting someone else's optimization framework. The most valuable thinking often happens in the spaces between systems, in gaps that allow for genuine reflection rather than immediate response.

What we're really talking about is how we structure the conditions under which thinking becomes possible. Obsidian offers one answer—not the answer, but an answer that prioritizes depth over speed, connection over categorization, ownership over convenience.

In a landscape designed to fragment attention and monetize distraction, maybe the most practical thing we can do is create quiet spaces where thoughts can actually think themselves through. Where the next idea isn't predetermined by an algorithm but emerges from everything we've noticed and cared enough to preserve.