The calendar app market is valued at over $5B and many calendar apps have raised millions with tech giants Dropbox and Notion acquiring Reclaim.ai and Cron respectively. Now of course productivity software continues to aspire to be an indispensable part of any busy professional’s workflow. Yet, as more companies race to create the “ultimate” productivity tool, there’s one crucial flaw in most calendar apps: they aren’t actually helpful. At least, not as well as they should.
Why? Because a calendar alone isn’t the main source of truth for how we prioritize our time. They likely should be, but currently calendars lack the context needed to make informed scheduling decisions. When a team meeting is set for 3 PM, is it because of an impending deadline or because the most important person in the room prefers that time? Calendars can’t tell us that. And therein lies one of the major problems.
the shift in calendar use
More people are using their calendars not just to block out time but to actively prioritize their day. It’s not just “what’s on the schedule,” but rather, “why aren’t I doing something more important right now?” The question becomes: what’s missing from these apps that could help people use their time better?
We need more than just a grid of dates and times. What if there were a to-do list or a notes app integrated directly into the calendar interface? Better yet, what if it was color-coded to help users audit their week visually and determine if their actions match their priorities? Similar to how developers use tools to track coding hours, professionals need an accurate depiction of how they’re spending their time, versus how they think they’re spending it.
Beyond just scheduling, we need personal reflection software—something that reveals the subtle ways we double up on time: a commute that becomes a conference call, a workout that also serves as personal time with a friend. These nuances of modern work life are invisible on a traditional calendar, but they are critical to understanding how we really spend our time and how we can create more time in our lives.
modern requirements
For a calendar app to truly work in today’s hyper-connected, multitasking world, it needs to:
- Be up to date in real-time: Sync instantly across devices and teams
- Make scheduling seamless: Suggest optimal times based on both individual preferences and team availability.
- Provide an intuitive overview: Offer quick snapshots of what’s important at a glance.
- Enable easy adjustments: Moving appointments and notifying participants should be effortless.
- Handle time zones effectively: Especially critical for global teams.
It’s no wonder email remains the productivity hub for most people—it’s where the real communication happens. Calendars are merely the secondary effect, a byproduct of scheduling decisions that email (or Slack) facilitates.
As AI assistants improve, tools like Calendly are focusing on the automation of meeting scheduling. By pulling data from calendars, emails, and preferences, AI assistants will increasingly be able to not only suggest meeting times but also factor in the human nuances that calendars currently ignore—like internal deadlines, personal energy levels, meeting priority, and optimal collaboration times.
the calendar of the future
Apps like Google Calendar, Fantastical, and Microsoft Outlook have advanced features like natural language processing and seamless syncing across services. But the future lies in integrating all the moving parts of a professional’s day: scheduling, tasks, and personal reflection. Tools like Any.do are already combining calendar functions with task management, and Vimcal offers time-blocking for focus, but there’s still much work to be done in creating a truly intuitive, all-in-one solution – sharing calendars soically, creating group calendars, conducting easier calendar audits (what RocketMoney does for budgeting, something should do for time).
The next wave of productivity software must go beyond just calendars. It needs to offer dynamic, context-aware, and reflective tools that can adapt to our increasingly complex work lives. Calendars alone aren’t cutting it anymore. We need tools that blend the precision of scheduling with the nuance of real-life priorities
(family commitments, work responsibilities, social events, aspirational content from social media, accurate travel times etc.), and until then, no calendar app will ever really “work.”
unpublished alpha 