For too long, our professional and personal time commitments have been siloed, with little crossover and much juggling required to bring those worlds together. A new category of productivity tools dubbed smart calendars are stepping up how you can take charge of your time and manage tasks regardless of how they’re categorized. We tried 4 great smart calendars that can be easily integrated with Sidekick. You can plug them into the sidebar and schedule your week using our handy split-view feature.
We found smart calendars fell into two categories–those that employ artificial intelligence and those that are like a to-do list on steroids. Both have some elements that overlap with project management tools. Regardless of the category, these tools are designed around the core precept of helping you get stuff done. They are best for people with consistent schedules, or for those trying to shape new habits and schedules.
Motion: the AI wizard. Automated but expensive.
Pro $34/month, $19/month billed annually
Team $20/month, $12/month billed annually (minimum five users)Learn more
Combines personal and professional tasks into one container
Flexible task prioritization and handy automated meeting scheduler
To be improved
Multiple upsells to team version
Some interface elements too subtle
Requires time to onboard
Motion is a time management platform that pulls together tasks and meetings alongside routines and personal commitments. It is one of the more expensive options we’ve seen, but it also is one with the most automation–assuming what it automates is what you find valuable.
Sign up with a Google or Microsoft account (credit card required for trial) and then jump right into the first of several intro videos explaining how to set up the next feature. The platform prompts you to add at least one calendar; once added, you can see the “other” calendars you have associated with your account. Next you’ll start adding tasks via a slick ctrl-spacebar shortcut in the dark-mode themed desktop.
We found Motion exceptionally useful for managing and assigning prioritization to tasks, and for shuffling and reorganizing those tasks manually or through Motion’s smart automation.
You have full editing access to your calendar from within Motion, and Motion tasks will sync back to your Google Calendar. Another great feature is a task backlog with granulation options.
We also liked the customizable and time-saving scheduling assistant. You can even add time blocks to your calendar (which will automatically shrink as your calendar fills).
The interface is largely clean and easy to navigate, but some details are cluttered and some nuanced design elements are too subtle. Expect a learning curve to get up and running and get tasks into the system, but it is clear that it can save time through its meaningful task prioritization and handy meeting scheduler. Also, it saves you a Calendly subscription as it has a similar conference planner.
Reclaim: bright and customizable
Pro $7.80/month, $6.50 annually
Team $9.50/month, $7.20 annuallyLearn more
Functional free tier
Sync multiple calendars (just one with free tier)
Customizable, flexible design
Reclaim currently can only be used if you have Google Calendar. A link on the site hints that Office 365 might be next on deck, but there’s no information as to when on the site. That limitation doesn’t mean Reclaim is solely for individuals; the service has a plan for teams as well. The service is designed around automation of both work and personal tasks, meetings, and habits.
To get started, sign in using your Google account. The service gets you started by asking some questions, like if you want to block off flexible time for lunch on weekdays, or to catch up on email during the workday vs. night and weekends. Next, you’ll connect your main calendar so Reclaim can block time for tasks accordingly. If you want to sync additional calendars you’ll need to graduate to the paid plan. The interface is simple.
A slide-out task pane at left breaks down the core functions to: planner (calendar view), stats, tasks, habits, Smart 1:1s, calendar sync. You can allow Reclaim to view and edit events on all calendars, and to see and download any calendar you access via your Google Calendar.
Reclaim uses bright colors and eye-catching graphics to differentiate their entries in your Google Calendar. Reclaim integrates with Slack, Google Tasks, Google Meet, and Zoom (paid version adds To-doist and Trello). The Smart 1:1s meeting scheduler finds mutual free time with your invitee, but this is only in the teams’ version. Even without the meeting scheduler and with its limits (you can only track three habits), the free version of Reclaim offers a good foundation for smarter and more automated task tracking.
Sunsama: planning guru and integration champ
Lets you make tasks from Gmail messages
Connects to and complements other services
Integrates with Notion, Gmail and many other apps
To be improved
Some UX elements are too subtle
Must manually drag tasks into calendar
Sunsama is less a smart calendar than it is a hub for your tasks, to-dos, and calendar to be accessed in the same space. It comes at the problem from a fresh angle, one that makes you focus on the day’s priorities with intention instead of simply reacting. You make your own decisions of what gets prioritized when. Basically, the app helps you build a planning habit.
After some onboarding questions, you’ll sign in with either Google Calendar or Outlook. Next Sunsama asks you to reflect on your past day’s tasks and activities, a clever way of helping teach the interface while leading to the next day’s tasks. Assign a task to a channel (offset by the ubiquitous hashtag). You can customize hashtags with color and sub-categories to make them more relevant.
The center of the workspace can toggle between tasks and calendar. Setting up tasks is fairly easy, and lets you enter as much, or as little, detail as you want. The interface is a bit obtuse at times. Moving a task to a different day–or onto your calendar–is an easy matter of drag-and-drop. A stats view shows how you’ve spent your time.
Sunsama’s real power lies with its app integration. Eight apps currently work with Sunsama, including Notion, Trello, To-Doist, and Gmail. The latter is especially compelling for being able to make an email a task so you remember to follow-up later. If email is more of a challenge than automating scheduling, then Sunsama’s approach will serve you well.
Premium $5.99 per month, $2.99 annuallyLearn more
Fast, simple task creation
Customizable tags (Premium version)
To be improved
Zapier integration remains an extra-cost
UX could be clearer
No automation beyond WhatsApp notifications
Any.do began as a more task-oriented platform, but now it handles much more. The free version has limited functionality, with fewer tasks and no WhatsApp reminder integrations, making the jump to Premium a no-brainer. Almost.
Any.do’s past as a task-centric service remains front-and-center. The interface is simple; on a desktop the interface resembles two phone vertical screens, one to show your lists and the other to show your calendar. A menu navigation pane sits along the left side of the screen. Create a new task by pressing the button in the pane, or by entering the task name into the field at the bottom of the Task screen.
You can add as little or as much as you’d like to a task entry, including notes, subtasks, and files. Set the time to be reminded, add to a list or add a tag. Both of these are customizable fields, but the tags and colors can only be customized on the Premium version.
If you enter a time to get a reminder, Any.do puts the task on your calendar for that time. We liked how efficient the interface was, complete with 15 keyboard shortcuts for quick data entry. We also liked that you could choose to print the day’s tasks, a sometimes handy if old-school approach.
Any.do requires a Zapier subscription to connect to email and other app services, an added cost which might explain the service’s comparatively low monthly price. The only app Any.do natively integrates with is WhatsApp, and that’s for handling Any.do’s notifications of when you should have tasks finished. The service remains a good, uncomplicated way of creating tasks and manually adding those tasks to your calendar. Just don’t expect anything too fancy.
These four smart calendar and task management platforms come in at different price tiers. Each takes a different approach to tackling the core problem staying on top of your tasks while juggling an already overloaded calendar.
If you’re ready for AI to take charge, look closely at either Motion or Reclaim. Both require onboarding to get your tasks entered, but the learning curve is surmountable. Motion costs more, but it is the only one of the bunch with full machine learning guiding when you’ll do tasks and how you’ll schedule meetings. We also found the dark mode interface more difficult to read than competing platforms that had a lighter look.
Reclaim is a strong choice for its more targeted use of AI plus its mix of habit building and personal calendar needs, including time blocking. It also has a scheduler to simplify scheduling meetings.
If tracking emails or integrating with other key apps is paramount, Sunsama is worth the look. Its Gmail integration in particular is attractive, as its ability to make prioritization decisions for yourself.
Any.do is the best bet for those on a budget, or those looking to dip a toe into the task tracking universe. It has less native functionality, but is facile and customizable. Sometimes simple is all one needs.