Programmable Ink
- title
- Scribble on your Google Calendar
- dated
- Q2 2025
Calendar apps and physical notebooks have very different vibes. Calendar apps are formal and visually uniform — just colored rectangles with titles that snap to a fixed grid. Notebooks have texture — you can use different pens and highlighters to mark and annotate however you want.
In our first prototype, we tried bringing both worlds together by starting with a digital notebook. We wanted to test whether the expressive freedom of pen and paper could coexist with synced digital events. The approach was to pull in your Google Calendar events as a static background layer, so you could sketch directly on top of them—circling important meetings, drawing arrows between tasks, or blocking out rough time estimates. Our goal was to preserve the iterative, flexible nature of notebook planning while still being able to see your scheduled events.
What we learned
Sketching on your calendar feels liberating Calendar apps force everything into uniform colored blocks, making it hard to distinguish critical meetings from your partner’s events that you just need to avoid scheduling over. Pen and highlighter are far more expressive - sketch tentative plans in gray, highlight time blocks, or jot quick notes without popups. When using sketchy calendar we found ourselves adding much more personal detail than in Google Calendar, capturing not just meetings but what we actually spent our time on.
It’s difficult to translate between the two worlds When building this prototype we struggled with how formal events and scribbles should interact. Should sketched events sync back to Google Calendar? Sure, we can use text recognition on handwriting, but you’d lose the implicit meaning of color and style. And how do you translate a roughly sketched time range into a fixed start and end?
The reverse problem is equally tricky — if you draw an arrow pointing to an imported event that gets rescheduled, should the arrow automatically move? A simpler solution might be stopping auto-updates once you’ve drawn on the paper, and just indicating when underlying events have changed so users can update manually.
It’s useful to have a distinction between formal events and rough scribbles In our prototype, Google Calendar events and hand-drawn scribbles remain quite separate. Initially we thought this was a problem, but there’s actually value in distinguishing between formal events with fixed times and loose sketchy plans. When meeting others, everyone needs to show up on time. But when planning for yourself, it doesn’t matter if you use personal shorthand that only makes sense to you in the moment. Our current prototype solves this by keeping scheduled events in Google Calendar and personal plans as scribbles. Even in a world everyone had automatically syncrhonized sketchy calendars, it’d still be useful to have distinction between formal and informal events.
It’s nice to have a dedicated device for daily planning Sketchy calendar feels like a notebook open next to your computer — you can see upcoming events alongside daily todos at a single glance. Having that context in your physical space keeps you aware of your priorities without switching away from your work. Unlike a physical notebook, the events stay synced, so when someone reschedules a meeting in Google Calendar, it automatically appears in your sketchy calendar.
Even without solving all the complex interactions between sketches and formal events, keeping them clearly separate proved surprisingly effective. The simple model of importing calendar events as a background layer while keeping all annotations as personal scribbles felt natural and useful. Next, we want to explore how this approach scales—what happens when you need to flip between days, weeks, or plan across an entire year?