Evolving Digital Calendars

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Derek Rosenzweig · Runtime Labs · July 4, 2026

Calendars are remarkably reliable surfaces for commitments — times, places, people, recurrence. What they lack is the context that matters most for human–agent collaboration.

iCalendar (.ics) was established in RFC 2445 (1998), and the current specification, RFC 5545 (2009), remains a text-based interchange format. It solved a narrower problem: synchronizing event records between systems. Start time, end time, title, location, recurrence, attendees — a portable text format Google Calendar, Apple Calendar, Outlook, and others could exchange. It worked well enough to become the default.

Shared Context and Timelines

A calendar event can hold a time and a place. It cannot hold the plan around it. Planning in the language-model era needs a richer unit of work:

Context on the timeline. Images, maps, notes, chat, and websites should sit with the commitment they belong to — not in separate apps the agent cannot see.

Trajectories, not just events. A trip, a launch week, or a project is a sequence: places to go, things to prepare, decisions made along the way. That sequence needs a durable home, not a pile of disconnected appointments.

Shared and mergeable timelines. Plans are collaborative. People and agents should be able to share a trajectory, adopt parts of it, and merge it into another timeline without losing the attached context.

Óra treats that context as first-class — images, maps, notes, chat, and links live on the same timeline as the events they describe.