Alex Obenauer's Itemized Personal Computing

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Alex Obenauer runs a one-person indie research lab from a homestead in New Hampshire, exploring what personal computing could look like if we started over. His work sits at the intersection of operating system design, knowledge management, and interface experimentation.

The core bet: today’s app-centric computing model is broken. Every piece of software creates its own silo. Your email app can’t see your calendar. Your task manager doesn’t know about your notes. You end up manually copying data between walled gardens, losing context along the way.

The Itemized Alternative

Obenauer’s response is the “itemized” paradigm. Instead of apps that own specific data types, everything becomes an item in a unified personal graph. Emails, calendar events, notes, tasks, web pages, PDFs — all nodes in one interconnected system.

From his Graph OS concept:

What if the entire operating system were to work like a notes graph? What if every individual digital thing could be linked or backlinked in your overall digital graph?

This isn’t theoretical. He built and lived in OLLOS from 2021 to 2023 — an itemized environment that uses time as its sole organizing principle. Everything appears in one chronological timeline: notes you write, emails you receive, events you schedule, tasks you complete.

The timeline creates automatic context. When you navigate to an email from last week, you see the calendar event you were in right above it, and the note you wrote right after. No manual linking required. Time does the organizing.

Working With The Lab Door Open

Obenauer publishes his research process through extensive lab notes — over 40 installments covering everything from universal data portability to gestural view construction. Each note documents work-in-progress ideas, often with working demos.

Key concepts from the lab notes:

He also built the Tag Navigator plugin for Obsidian, demonstrating cross-reference navigation in existing software.

Before The Lab

Obenauer isn’t new to building software people actually use. Mail Pilot reached #1 in the Mac App Store and introduced email patterns that later became standard (The New York Times called it “ingenious”).

During 2020’s lockdowns, he built 1997.chat — a faithful recreation of AOL Instant Messenger, complete with sounds, away messages, and animated buddy icons. It connected isolated people through nostalgia and was later acquired.

The Membership Model

The research is funded by a community of 70+ members who support his Little Lab. Members get early access to demos, experiments, and essays that may or may not become public.

This model lets him work on long-term speculative projects without needing immediate commercial viability. The itemized OS work spans years of daily use and iteration.

Core Principles

Several themes run through Obenauer’s work:

Items over apps. The smallest useful unit is the item (an email, a note, a task), not the application. Apps should be thin views over shared data.

Time as infrastructure. We naturally think in temporal terms. Digital environments should respect that instead of forcing artificial hierarchies.

Universal linking. Any item should be able to reference any other item. Transclusion (embedding live references) beats copy-paste.

User-evolvable systems. People should be able to modify and extend their computing environments without waiting for software companies.

Practical Takeaways

For builders experimenting with personal computing:

  1. Try living in your own tools. Obenauer used OLLOS as his primary environment for two years. Dogfooding reveals what actually matters.

  2. Publish your process. Lab notes invite collaboration and refine thinking. “Working with the lab door open” attracts people solving similar problems.

  3. Question the app model. When building something new, ask: could this be a view over existing data instead of a new silo?

  4. Use time as a default organizer. Chronological ordering is free context. Many items don’t need explicit categorization if they’re timestamped.

Resources