How the CEO of Obsidian Takes

File Over App & Radical Minimalism #

• The Foundation: Obsidian vaults are simply folders of Markdown (.md) files. The "file over app" philosophy ensures your data outlasts the software; you are not locked into a proprietary system.
• Folder Avoidance: The CEO of Obsidian, Stephango (Kipano), avoids complex folder structures because notes often belong to multiple categories.
• The Root Directory: Most notes (journal entries, essays, evergreen notes) live in the "root" of the vault rather than subfolders. This reduces the friction of deciding where a note "should" go.

Organization via Properties and Categories #

• Metadata over Folders: Notes are organized using the "categories" property in the YAML frontmatter (the section between --- lines).
• Property Types: Properties can be text, numbers (like ratings), or dates.
• The "Categories" System: In this vault, "Category" notes (e.g., "Meetings," "Journal") act as smart hubs. They use the Dataview (or "basis") feature to automatically list every note that has that specific category assigned in its properties.
• Navigation: Instead of using the file explorer, use the Quick Switcher (Cmd/Ctrl + O) to find category notes or specific entries.

Templates for Speed and "Laziness" #

• Template-First Workflow: Almost every note starts with a template to "lazily" add metadata that makes the note discoverable later.
• Specific Templates:
  • Meeting Template: Automatically adds properties for date, people present, and topics.
  • People/Author Templates: Use these for contacts or writers; they often include a "backlink" table showing every time you've mentioned or met that person.
  • Reference Templates: Used for things "outside your world" (movies, books, podcasts), often kept in a separate References folder.
• Unique Note Creator: A core plugin used to create time-stamped files instantly, serving as the default starting point for thoughts.

Advanced Linking and "Evergreen" Notes #

• Heavy Internal Linking: Link the first mention of any concept, person, or place. This allows you to trace the "branching paths" of how your ideas emerged over time.
• Unresolved Links: Creating links for things that don't have notes yet sets an "indirect intention" to potentially develop those thoughts later.
• Evergreen Notes: These turn complex insights into "objects." By giving a specific idea its own note (tagged as "Evergreen"), you can reference and manipulate that single idea across many other notes.
• Rating System: A 1-7 scale is used to rank how "life-changing" a piece of media or an experience was (7 being the highest).

The CEO’s Review Rhythm #

• Daily: Write down spontaneous thoughts or journal entries in unique, time-stamped notes.
• Every Few Days: Review recent notes to compile and aggregate related thoughts into more cohesive summaries.
• Weekly: Create a radically simple markdown checklist for tasks.
• Monthly: Use a "Monthly Note" template to reflect on high-level patterns and the "idea aggregations" made during the month.
• Quarterly/Yearly: Use the "Open Random Note" feature to rediscover old ideas and perform an annual review using a set of 40 specific reflection questions.

Summary #

The Obsidian CEO’s note-taking system is a masterclass in "productive chaos." By rejecting strict folder hierarchies in favor of a flat root structure, the system prioritizes speed and reduces the mental overhead of organization. It relies heavily on metadata properties and automated templates to create "smart" category hubs that organize themselves. The core philosophy is to treat ideas as interconnected objects through aggressive internal linking, allowing a network of knowledge to emerge naturally over time. It is a flexible, minimalist framework designed for "lazy" but effective long-term thinking and reflection.