File Over App: A Deep Analysis of Digital Longevity

TL;DR: Steph Ango's "File Over App" philosophy argues that the files you create are more important than the tools you use to create them. Apps are ephemeral; files can last forever. Choose open formats, store locally, and own your data.

About This Analysis

This analysis applies a structured framework to examine Steph Ango's (kepano) "File Over App" philosophy — a manifesto for digital longevity that has become foundational to the local-first software movement.

Source: kepano on X and stephango.com/file-over-app

I. Core Content (What)

The Central Thesis

"The files you create are more important than the tools you use to create them."

This deceptively simple statement contains a profound insight: software is ephemeral, but data can be permanent — if stored in the right formats.

Key Concepts Defined

Concept
Definition

File Over App

Prioritize durable file formats over application-dependent storage

Digital Longevity

Files from 2060 should be readable on computers from 1960

Data Ownership

Users fully own their data, not the app vendor

Plain Text Primacy

.txt/.md files are the most durable digital format

Local-First

Data stored locally is primary; cloud is supplementary

Structure of the Argument

  1. Historical precedent: Ideas carved on clay tablets and paper outlasted their tools

  2. Modern problem: Cloud apps lock data behind logins, proprietary formats, and internet dependency

  3. The durability test: "If you want your writing readable in 2160, it must be readable on a computer from 1960"

  4. Solution: Use open formats (Markdown, plain text, JPEG, PDF)

  5. Call to action: Tool makers should grant users genuine data ownership

Evidence Provided

  • Egyptian hieroglyphs: The carved ideas outlasted the specific chisels used

  • Dropbox Paper: Stores URLs instead of actual content — a cautionary tale

  • Plain text from 1985: Still perfectly readable on any modern computer

  • Obsidian's approach: Markdown files in a local folder you own

II. Background Context (Why)

Who is Steph Ango (kepano)?

Attribute
Detail

Current Role

CEO of Obsidian (since February 2023)

Previous Work

Co-founded Lumi and Inkodye

Path to CEO

Started as a "superfan" power user

Personal Practice

Publishes plain text files via Jekyll/Netlify

Historical Context

The "File Over App" essay emerged during a perfect storm:

  • Cloud SaaS dominance: Google Docs, Notion, and similar apps became ubiquitous

  • The Google Graveyard: Increasing awareness of service shutdowns (Google Reader, etc.)

  • Privacy concerns: High-profile data breaches at centralized services

  • Local-first movement: Ink & Switch's seminal 2019 essay laid theoretical groundwork

The Intent Behind the Philosophy

Element
Description

Problem addressed

Vendor lock-in, service discontinuation, data loss

Target audience

Knowledge workers, developers, tool makers

Ultimate goal

Shift industry norms toward user data ownership

Unstated Assumptions

  1. Users will prefer control over convenience features

  2. Open formats are sufficient for most use cases

  3. People value long-term preservation over short-term features

  4. The market will eventually reward ethical data practices

III. Critical Scrutiny

Counterarguments and Responses

Objection
Ango's Position

"Collaboration needs servers"

Local-first CRDTs enable real-time collaboration without central authority

"Plain text limits functionality"

Markdown + plugins can replicate most rich features

"Users don't care about this"

Growing market for privacy-focused tools suggests otherwise

"Sync is too hard without cloud"

Obsidian Sync, Syncthing, iCloud prove it's possible

Potential Weaknesses

  1. Survivorship bias: Focuses on formats that survived; doesn't analyze successful proprietary formats

  2. Technical barrier: Managing local files requires more user sophistication than cloud apps

  3. Network effects: Cloud apps benefit from collaborative features that File Over App de-emphasizes

  4. Enterprise gaps: Doesn't address compliance, audit trails, or access control needs

Boundary Conditions

Philosophy works well for:

  • Personal knowledge management

  • Note-taking and journaling

  • Static documents (writing, research)

  • Individual archival needs

Philosophy struggles with:

  • Real-time multiplayer applications

  • Complex structured data (spreadsheets, databases)

  • Enterprise workflows requiring granular access control

  • Users who prioritize convenience over ownership

What's Missing

  • No discussion of Git integration for version control

  • Limited treatment of end-to-end encryption

  • Ignores mobile-first users who prefer cloud simplicity

  • Doesn't address how enterprises could adopt this approach

IV. Value Extraction

Reusable Frameworks

1. The Durability Test

Ask: "Can this file be read in 100 years without any special software?"

2. Ownership Checklist

Before choosing a tool, verify:

3. Tool Selection Hierarchy

Prioritize in this order:

  1. Open formats (Markdown, plain text, PDF)

  2. Features (what you actually need)

  3. Convenience (nice-to-have UX)

Role-Specific Takeaways

Role
Key Lesson

Developer

Build export-first; support open standards from day one

Knowledge Worker

Use Markdown for notes; avoid proprietary lock-in

Enterprise Architect

Evaluate SaaS vendors on data portability

Digital Archivist

Plain text + PDF for guaranteed long-term preservation

Startup Founder

Consider "File Over App" as a competitive differentiator

Mindset Shifts

From
To

"App features matter most"

"File durability matters most"

"Trust the cloud provider"

"Own your own data"

"Convenience now"

"Accessibility forever"

"Lock-in is inevitable"

"Portability is achievable"

"Apps define my workflow"

"Files outlive any app"

V. The 7 Local-First Ideals

The Ink & Switch research lab defined seven ideals that complement File Over App:

#
Ideal
Description

1

No Spinners

Instant response; no waiting for servers

2

Multi-Device

Sync across all your devices seamlessly

3

Optional Network

Full functionality offline

4

Seamless Collaboration

Real-time editing without central servers

5

The Long Now

Data accessible indefinitely

6

Security & Privacy

End-to-end encryption possible

7

Ownership & Control

Users have full agency

VI. Practical Implementation

Durable File Formats

Format
Longevity
Best For

.txt

Centuries

Universal notes, logs

.md

Decades+

Structured notes, documentation

.pdf

Decades+

Final documents, archival

.jpg

Decades+

Photos, images

.html

Decades+

Web content

Tools That Embrace This Philosophy

Tool
Format
Notes

Obsidian

Markdown

Local-first, plugin ecosystem

Logseq

Markdown/Org

Open-source outliner

iA Writer

Markdown

Focused writing

Zettlr

Markdown

Academic writing

SilverBullet

Markdown

Open-source PKM

Emacs + Org Mode

Plain text

Ultimate flexibility

Migration Strategy

  1. Audit current tools: What formats do they use? Can you export?

  2. Export everything: Get your data out of locked systems

  3. Convert to open formats: Markdown for text, PDF for finalized docs

  4. Establish local storage: A folder structure you control

  5. Add sync as needed: Obsidian Sync, iCloud, Syncthing

  6. Build new habits: Create in open formats from the start

VII. Conclusion

The Core Message

Steph Ango's "File Over App" philosophy is a call to reclaim ownership of our digital lives. In an era of cloud dependency and service shutdowns, it offers a path to true data sovereignty.

Key Takeaways

Principle
Action

Files over apps

Choose tools that respect open formats

Local over cloud

Store data on your device first

Open over proprietary

Prefer Markdown, plain text, PDF

Ownership over convenience

Accept some friction for true control

Longevity over features

Think in decades, not product cycles

The Ultimate Test

"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."

Plain text passes this test. Does your current tool?

Sources

Primary Sources

Community Analysis

Discussions

Appendix: Diagrams

Visual learning resources included:

  • file_over_app_philosophy.pdf - Comprehensive knowledge infographic

  • cloud_vs_local_first.pdf - Cloud vs Local-First comparison chart

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