How Mac experts manage their calendars

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There was a time when I managed my calendar by keeping a Post-It note with important meetings written down on it. That hasn’t worked since the late 1990s, though.

Today, I rely on Google Calendar to keep my appointments in sync between my Mac and my iOS devices. I use Fantastical and Apple’s Calendar on my Mac, Fantastical on the iPhone, and Calendar on the iPad. I’m okay with my approach, but some Apple power-users I spoke to had alternative approaches that are worth considering.

Jacqui Cheng

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Jacqui Cheng is the editor-in-chief of The Wirecutter. Like me, she uses Google Calendar as the “main hub” for all her calendar syncing. “This started back when I still had an office job and was using a Windows PC to program on,” meaning iCal and iCloud weren’t even options at the time. Because all the major calendar apps sync with Google Calendar now, “it’s too much of a mess for me to extract into anything else.”

Jacqui says that she uses her Mac and iPhone equally for adding appointments. “On the Mac, I just use the Google Calendar page on the Web, because I usually already have it open.” On the iPhone, she uses Apple’s Calendar app, which has Google sync built in as an option.

I’ve often expressed my affection for Siri (whom I call my best friend in New Jersey), and I use the voice assistant to create appointments fairly often. Jacqui, however, only uses Siri for that purpose “very occasionally.” But Jacqui has ended up with a few too many appointments that say something like “Tell Maude avocado Wednesday three P” whose original meaning eludes her.

Jacqui has other complaints about the modern state of calendar management, too. “Syncing in general can still be an issue,” she says, “especially when there are multiple people in a household who might have their own calendars and shared calendars.” She explains that her shared calendar situation with her husband is “a disaster,” since he relies on iCloud. When certain appointments must be shared, she ends up needing to make two versions: one on her own calendar, and one on the shared version: “It’s a pain, and I hate it.”

Her advice: “Just like kids, budget, and housing, talk to your significant other about his or her preferred calendaring solution before you get married.”

Joe Kissell

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Joe Kissell is an editor at TidBits, and a Macworld senior contributor.

Unlike Jacqui and me, Joe uses iCloud for syncing calendars. “Unlike some parts of iCloud, I’ve found calendar syncing to be highly dependable,” he says, “and the convenience of sharing calendars with my wife makes [iCloud] ideal for my needs.”

Because his schedule is very light (“many weeks I can count my meetings and appointments on one hand”), Joe finds that he only needs to add appointments to his calendars “a couple of times a week, not multiple times a day.”

Joe uses BusyCal on the Mac, and Apple’s built-in Calendar app on iOS. “I’ve tried lots of other calendar apps, but I find I don’t need all the extra bells, whistles, and shortcuts.” He first embraced BusyCal “back in the days [when iCal’s] UI was truly awful, and BusyCal made things so much simpler for me.” Despite improvements to Calendar in Mavericks, Joe says, he still prefers BusyCal—”including the fact that it still integrates to-do items, and the built-in weather forecast.”

While Joe uses Siri to schedule reminders (“Remind me to return Lex’s phone call after lunch”), he doesn’t use the assistant for scheduling appointments: “I’m virtually never in a situation where Siri would be helpful for that.”

Like Jacqui, Joe finds it frustrating to book meetings with people who use alternate calendaring solutions. “Tracking availability and response status is hit-and-miss at best,” he says. “Dealing with meeting invitations is confusing for everyone involved.”

Joe’s best advice for keeping calendar management simple: “Have fewer meetings. That simplifies things enormously.”

If that’s not an option, Joe’s backup advice is that it’s worthwhile to give your spouse the ability not just to view your calendar, but to edit it as well. With his own wife, Joe says, “it’s hugely helpful for us to be able to add events to the other person’s calendar, as well as to a Family calendar.”

Shawn Blanc

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Shawn Blanc runs the coincidentally-titled Like Joe, he uses iCloud for calendar syncing. His calendars have “been there since the days of .Mac and iCal, which I went with back in 2005—because that’s what was around when I started being grown up and busy enough to warrant keeping a calendar.”

Like me, Shawn adds appointments from his Mac and his iPhone in equal measure, and he uses the same app I rely on: “I use Fantastical for both iPhone and Mac because it’s the best calendar app out there; its natural-language input makes adding events much faster from the iPhone, and I love how on the Mac it lives in the Menu Bar and can be brought up with the flick of a keystroke.”

Shawn and I are almost twinsies, because he uses Siri to schedule appointments sometimes, too. “It’s not often, but when I do use Siri I simply ask her to make a new event and give her the details of name and time” when prompted. For my part, I usually say, “Make an appoint for 2pm on Feb 18th called ‘Meeting with Dan.’”

Like many folks who use both iOS devices and Macs, Shawn encounters a daily frustration: “When I’m at my desk and an event reminder goes off on my Mac, iPad, and iPhone all at the same time—it’s like a fire drill.”

Shawn’s calendar advice echoes Joe’s: He consolidated all his calendars (work, personal, and the like) into just two—one called Shawn, and another called Anna (his wife’s name). Like Joe, Shawn set up each calendar so that both he and his wife could see and edit each other’s events. “That has made managing our two schedules quite a bit easier.”

The downside to Shawn’s approach—which is the one I use as well—is that when my wife and I share an event on each of our unique calendars, I’ll see two copies of it side by side when I look at that date. That’s why Joe endorses a calendar for you and your spouse, and a third calendar for shared events.

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