I have a complicated relationship with Obsidian. Actually, I have a complicated relationship with the entire tech sphere right now.
Between the AI model wars trading punches every few days and the undeniably strange cast of characters running these tech giants, it is hard to figure out which tools are actually built to last. But my conflict with Obsidian goes deeper than just the software.
It is a conflict of philosophy.
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The File Over App Rebellion
In case you aren’t familiar, Obsidian is a markdown, plain-text notes app. It is entirely user-supported, built by a tiny team of less than 10 people. The CEO is adamant about not taking VC money and not growing the team. Instead, they rely on a massive ecosystem of community-built plugins to drive new features.
On one hand, this is a beautiful rebellion against modern software.
Their entire ethos is “file over app.” By default, everything lives on your computer’s hard drive as plain text. You own the files. If Obsidian ceases to exist tomorrow, you don’t lose a single word.
This philosophy was born out of trauma.
If you used Evernote back in the day, you probably remember the exact moment you felt trapped. They jacked up the subscription prices, and suddenly, users with tens of thousands of notes realized they had no recourse. They didn’t own their data; they were just renting access to it.
Obsidian is the ultimate insurance policy against that ever happening again.
Is It Worth The Friction?
But here is where the tension lies: Is an insurance policy worth the friction?
In today’s hyper-competitive economy, it is incredibly easy for a tiny, stubborn company to get replaced. A well-funded competitor can come along, clone the best features that Obsidian’s community spent years building, wrap it in a better user interface, and take over.
Obsidian’s defense to that threat is essentially, “Well, you have your files, so you can easily move to the new app.” It is a wildly counterintuitive way to run a business. The leadership comes off as condescending—sitting on a moral high horse about “free” apps and local files.
And frankly, regular people don’t care about markdown files. They don’t know what a terminal is, let alone how to open one. They just want an app that works.
The Notion Dilemma
Take Notion, for example.
In my circles, people love to crap on Notion because it is online-only, you don’t own the files, and you have to pay for it.
I even crap on Notion for those exact reasons.
But I will admit this: Their implementation of AI is arguably the most useful out of any app on the market.
It has the full context of your entire database built-in. You can tag a specific document and ask it questions directly. It is frictionless. Yes, your data is locked in the cloud, but you are actually getting work done.
The Tinkering Trap
Personally, I am still caught in the middle. I just set up a brand new Obsidian vault specifically to manage the markdown files for my website, entirely separate from my “second brain.” It is incredibly satisfying to write a post, keep all the connections, and then literally just drag the markdown file into the right folder to push it to the live site.
But I also have to ask myself: Is this actual productivity, or just a sophisticated form of procrastination?
Tinkering with tools—whether it is setting up a new Obsidian workflow or using Claude Code to rebuild a website—is fun.
I have an engineering brain; I enjoy the tinkering. But it is a huge distraction. When you are trying to juggle a YouTube channel, a podcast, a newsletter, and content across Threads, X, and TikTok, the system often breaks down.
Recently, I found myself completely losing track of what I had scheduled to post and where.
Despite all the philosophical debates about data ownership and the magic of plain text, I still find myself plugging away in Apple Notes for my day-to-day life.
I wish it looked better.
I wish it had more features to handle the sheer volume of stuff I have going on.
But it just works.
Ultimately, the tool you use matters infinitely less than what you put into it. The “file over app” mindset is great for preserving your history, but if the app itself is causing you to spend more time organizing than creating, it might be time to rethink the system.
I think this is an interesting perspective and one that I resonate with in part.
I was a pen and paper user, then a Notion user, then a Roam Research user. The move to Roam really started my interest in the "tools-for-thought" space, but I have found it not a good community to be part of at times. Roam in particular was very toxic, where if you did something slightly against the norm you were shit upon.
I also found that being an active member of the community lead me to being more of a tinkerer, constantly looking for new or better ways to do things and a good part of that was the peer pressure of someone saying "you should do this X way rather than how you are doing it".
Notion for me is probably one of the worst here too, just because there is a lot of functionality. If something doesn't work quite right, then it will bother me and I won't be able to leave it until I have resolved it. This is where I lost most of my time.
Moving to Obsidian, I have quite intentionally tried to keep it as simple as possible, and also kept away largely from the community. My initial vault set up took maybe a few weeks, and it has stayed pretty much exactly the same for the last four/five years. It is simplistic, and that works well for me. It's that mindset that has resonated for a lot of people who aren't interested in the tinkerer aspect of the community.
Every now and then I will get a stray comment about how I haven't utilised bases or some newer feature in Obsidian - but I try and ignore it.