Steph Ango's File Over App Philosophy

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Steph Ango runs Obsidian, the note-taking app with a cult following among people who care about owning their data. But his approach to personal AI systems is refreshingly contrarian: he’s skeptical of delegation.

“Don’t delegate understanding,” he writes. The core argument is simple—if you outsource thinking to AI, you lose the compound returns of building your own knowledge. The process of maintaining your notes matters as much as the notes themselves.

The File Over App Manifesto

Ango’s philosophy starts with a bet: your files will outlast any app you use to create them.

If you want your writing to still be readable on a computer from the 2060s or 2160s, it’s important that your notes can be read on a computer from the 1960s.

This means plain Markdown. No proprietary formats. No vendor lock-in. When someone asks him about AI-powered note organization, his response cuts against the grain—he actually enjoys doing manual maintenance on his vault. It helps him understand his own patterns.

Fractal Journaling

His daily system works bottom-up, not top-down:

Throughout the day: Quick capture with timestamped notes (YYYY-MM-DD HHmm format)
Every few days: Review fragments, compile the good stuff
Monthly: Review the daily compilations
Yearly: Review monthly reviews using his 40 questions template

The result is what he calls “fractal journaling”—you can zoom in and out of your life at varying levels of detail. Every big idea can be traced back to the small thought that sparked it.

Where AI Fits (and Doesn’t)

Ango isn’t anti-AI. He coined “synthography” for AI-generated images and wrote about “Photoshop for text”—the idea that text manipulation will become as seamless as image filters.

But he draws a hard line on one thing: AI should run locally, on your device. No cloud dependencies. No server-side processing. This aligns with his file-over-app worldview—if your AI tools require internet access and proprietary APIs, you don’t really own the workflow.

His prediction: local language models will make text transformation “as mundane as Gaussian blur.” The key word is local.

The Vault Structure

His Obsidian vault is deliberately simple:

Root folder: Personal notes, journal entries, evergreen notes
References/: Things that exist outside his world (books, movies, people)
Clippings/: Stuff other people wrote
Attachments/: Media files
Daily/: Date-named notes for linking, never for writing

The controversial rule: avoid folders for organization. Most notes live in the root. Categories come from properties and tags, not directory structure.

Rules That Create Freedom

He maintains a personal style guide:

Always pluralize tags (so you never wonder: book or books?)
Use internal links profusely, even to notes that don’t exist yet
YYYY-MM-DD dates everywhere
Ratings on a 7-point scale (10 is too granular, 5 isn’t enough)

Having consistent constraints means you don’t waste mental energy on formatting decisions. The style guide makes every future decision automatic.

Building in Public

Beyond Obsidian itself, Ango maintains:

Minimal: A distraction-free Obsidian theme (4.7k GitHub stars)
Flexoki: An ink-inspired color scheme for prose and code
Defuddle: Extract clean content from web pages (useful for saving articles)
His vault template: Downloadable starter for his approach

The common thread: tools that respect file ownership and work offline.

The Anti-Delegation Stance

When people ask if he’ll automate his fractal journaling with LLMs, his answer is no:

I enjoy this process. Doing this maintenance helps me understand my own patterns.

This is the opposite of the “AI for everything” maximalism you see elsewhere. Ango’s take: some cognitive work shouldn’t be optimized away. The friction is the point.