Technical tools: Calendar management

When’s the last time you had someone book a calendar appointment on top of an existing commitment of yours? When’s the last time it was you doing it, because you were looking at one calendar & the conflicting block was on another?

Managing calendars, appointments, and availability across your home and work life when you’re working with multiple clients or organizations can be a frustrating, trying experience. I myself have tried the span of options from daily-handwritten templates copying events from a larger tracked calendar, using a given client digital calendar almost exclusively, manually copying events back and forth as iCal files, surrendering control entirely (don’t do this), merging everything that comes up into a Moleskine paper day planner, and probably others that failed to make an impression on me.

My current setup is the best balance I’ve found. It remains imperfect, and I’m more than happy to hear your suggestions–but in the meantime, I hope this can help you smooth things out for yourself & skip some of the long trial-and-error process I went through.

(some referral links follow)

Google Calendar for most stuff

I do not love Google Calendar, but virtually everything out there expects you to use it, particularly in the software business world. I have one FastMail account whose calendar I use, and I end up having to use their inbuilt Google Calendar Sync functionality to link into anything else.

Maybe Microsoft would work for you, depending on your use case? GCal is hard to avoid.

Reclaim.ai for calendar sync

Reclaim smartly does two-way event synchronization between your calendars. You can set it to include details or just mark things as “Busy”, “Personal”, “Work Commitment”, or similar, so your protologist’s appointment won’t show up on your client’s calendar.

There’s a bunch of extras for teams (which might be nice, haven’t tried them) and for auto-injecting tasks synced in from your favorite corporate ticket-tracking tool (Jira, Linear, others); I’ve found that just setting aside a block of time for uninterrupted work is the best approach for me, and the rest gets too fiddly.

Reclaim only works with Google Calendar. If you happen to be on another service, you may not be out of luck–some competitors have a much more basic “sync to one Google Calendar” feature, and you can use a dummy calendar as a proxy. I do this with a FastMail account without much issue. My understanding is that CalmCalendar gives more flexibility here, and I may have to check that out at some point–but for the moment, Reclaim is sufficient to not spent time investigating alternatives.

I frequently describe Reclaim as “just good enough that it keeps me from building a competitor”, and thank goodness it is, because calendar sync is a wide field of programmer rabbit holes.

Fantastical as Calendar.app replacement

If you’re on Windows, I don’t know what to recommend. If you’re on Linux, you probably already have a strong opinion here. But if you’re on a Mac and in the Apple ecosystem, you should throw away the default Calendar.app and swap to Fantastical immediately.

Unlike the other offerings here, I can recommend Fantastical without reservation (and without profit; that’s not a referral link). It’ll sync with darn near anything, plays nice with Reclaim (and reportedly CalmCalendar), feels like an actual Mac app, has great display options, deals with incoming appoint requests reliably, understands natural language for appointment creation, and (I especially love this) merges the display of identical entries on multiple calendars, so you can actually read them.

It’s also starting to step on the toes of Calendly and SavvyCal with its Openings feature to let people book appointments with you. I haven’t tried this yet, as I’m happy with SavvyCal and Openings doesn’t yet integrate with any sort of payment platform. Worth keeping an eye on, though, and this may be sufficient for your use case without adding and maintaining yet another paid tool.

SavvyCal for appointment booking and management

It’s like Calendly, but indie, non-corporate, with some serious UX magic (your clientele can overlay their own calendar while checking availability). It syncs with most popular calendars and integrates with Stripe for paid appointments. You can use it to automate finding a timeslot for a meeting with multiple people without all the back-and-forth of Slack and email and whatnot.

It does the things and it’s not the evil empire. If you haven’t used an appointment management service before, let me insist: even one use a month is worth the monthly fee to not have to think about coordination.

Invisible Calendar for a desk calendar

I live in my calendar and want it open all the time. I also love the gentle, non-invasiveness of e-ink screens. The Invisible Calendar sits attractively in my line of sight on my desk, close enough to a paper calendar, but without any of the manual copying back and forth from paper. Superb.

Things I (somewhat surprisingly) don’t use

I could nerd out on calendar tooling virtually forever, but it’s not what I get paid for. Consequently, I don’t pull my stuff into org-agenda, nor play with SavvyCal’s API access; I don’t bullet journal or sketch a paper daily agenda (though the latter has proven useful historically).

If something here jumps out at you, or if the whole system sounds reasonable, borrow bits and pieces or take the whole thing. Happy scheduling!