Most software improves over time. Calendars didn’t.
The calendar you use today is basically the one your boss used in 1998. It’s an artifact of Outlook and Lotus Notes. That’s why it feels like a tool for corporations, not for humans.
1. Calendars Are Designed for Work, Not Life
Digital calendars were built for organizations, not individuals. That’s why your boss can drop meetings on your schedule without consent. Your calendar is less yours than your employer’s. It’s a tool for control, not a tool for living.
2. The Grid Is Wrong
Time in calendars is presented as a grid of rectangles—a relic of train schedules and factory shifts. Real time is lived, nonlinear, unpredictable. At best the grid feels like a spreadsheet. At worst, like a cage.
3. Calendars Aren’t Visual
Humans remember things visually: flyers, screenshots, posters. Calendars strip that away. Adding an event means translating a visual memory into a form field. Instagram hooks us because it aligns with how we actually process information. Calendars ignore it.
4. Adding Events Is Painful
To add an event you either fill out a form or learn the quirks of a “natural language” parser. Both are slow. You do it because you have to, not because you want to. Adding a contact used to feel like this, but that got easier. Events didn’t.
5. Text Fields Are Awful
The description box is one of the worst text fields on the internet. Formatting is broken, links render inconsistently, emojis often fail. Billions of people rely on it, yet it feels like a forgotten corner of the web.
6. Sharing Sucks
To invite someone, you need not just their email but the right email tied to the right calendar. You can’t invite with a phone number. Invites demand a yes/no/maybe instead of letting people casually add or consider. Calendars force decisions when real life is ambiguous.
7. Permissions Suck
Modern apps solved collaboration: invite, accept, clear permissions. Calendars never did. Event-level permissions are opaque. Can they edit? Who sees edits? It’s guesswork. It feels like Google Docs before real-time editing existed.
8. Time Zones Confuse Everyone
Time zones are inherently hard. Calendars don’t make them easier. They mostly mirror the confusion instead of fixing it.
9. Calendars Don’t Play Nice with the Internet
Calendars are walled off. Events don’t have universal links. Embeds look bad and require messy permissions. To put a calendar on a website you usually have to make the whole thing public, which no one wants. Individual events should behave like links, but they don’t. Calendars still behave like desktop software pretending to live online.
10. Calendars Don’t Handle Options
Calendars assume certainty. You’re either in or out. Put three events in one slot and you get illegible vertical slices. Real life means juggling possibilities. Calendars collapse under that.
11. Recurring Events Are Lies
Recurring events look good when you create them. In reality, they outlive their usefulness. They linger as ghosts for months or years. A system meant to reflect reality ends up reflecting inertia.
12. Bad on Mobile
Most calendars shrink a desktop view onto a phone. They force left-right scrolling when every other mobile interface is vertical. A simple list would often work better. Instead we get clutter.
13. No On-Ramp for New Users
Only about half of people use a digital calendar. There’s no friendly onboarding for those who don’t. Calendars assume everyone is already inside the system, which makes adoption brittle.
Where Calendars Could Go
It doesn’t have to be this way. Digital calendars have enormous potential. They could help us see and plan our time, visualize the future, coordinate with other humans, and design the life we want. That’s what makes them worth fixing.
The problem is today’s calendars aren’t giving us the tools we need. We don’t just need a grid for meetings. We need something built for how people actually live: social, visual, and unpredictable.
That’s what I’m working on with Soonlist, exploring how to evolve calendars with AI. If you care about the future of calendars, reach out.