ISO a tidy digital calendar (2019 edition)

March 6, 2019 9:32 PM

I'm starting a new job that will have lots of meetings and schedule coordination, and before I get rolling with it, I would like to fix my calendar problems. I'm looking for a solution that will work with my iPhone, Mac desktop, and work Outlook calendar and allow me to sync up all my personal and professional appointments as well as my husband's calendar. More on my wish list within!

My current setup involving Google Calendar, Calendar (for Mac), and an old version of Fantastical is a mess and has a bunch of old recurring events I can't figure out how to eliminate (some of them may be tied to contacts - I really don't know at this point). I don't mind paying within reason for the new solution if necessary - the functionality is the most important thing.

Must have:
- the ability to sync across iPhone and Outlook for Mac (at a minimum)
- the ability to show my personal appointments, my husband's appointments, our joint appointments, and my work appointments (and preferably differentiate each of these)

Would like to have:
- the ability to make a global setting that will show my personal and joint-with-my-husband appointments as "busy" on my work calendar (Outlook) but not necessarily show details (i.e., make them "Private Events") (this would be handy because my Outlook work calendar may be shared with others who need to know my availability but don't really need to know all my business)
- the ability to sync across either a web-based tool a la GCal and/or Calendar on my Mac desktop as well as my phone and Outlook for Mac

If the tool also has reminders/to-do lists and/or a contacts component, I'm down for that. (Those are both a huge mess for me as well but the scheduling/calendar is my most pressing concern at the moment.)

Part of the solution will likely need to involve cleaning up the old calendars and recurring events - if anyone has any tips for making that less painful, please share!

posted by pupstocks to Grab Bag (4 answers total)

The baked-in Mac calendar app does all of these things except perhaps the "show my other calendars as busy on my Outlook" -- I'd be interested to know that I'm wrong about that though, because currently I use the Mac calendar to see all my Outlook and Google Calendars together, and I just duplicate personal events on my work calendar and mark them private as necessary. Anyway, just add whatever accounts you want to see in your calendar to your Mac calendar and you should be good to go. For the old stuff you can't get rid of -- hopefully that's just Fantastical and you can just abandon it?
posted by rabbitrabbit at 6:07 AM on March 7, 2019

Dr. Advicepig and I share our shared events on a Google Calendar. My whole calendar life in on Google. Work uses Google Apps, my own events are in Google Calendar, this shared calendar, all of it. I use the Google Calendar App on my iPhone. It's pretty much fine.

Dr. Advicepig insists on using the Apple Calendar app on her iPhone and Mac. It's kind of inscrutable as to when it syncs or how to force it to. Every few months, it gets her almost mad enough to switch, but for a reason she can't articulate, she hasn't.
posted by advicepig at 6:12 AM on March 7, 2019

Seconding that Apple Calendar will just randomly not sync with Google Calendar and it is very frustrating.
posted by soelo at 8:28 AM on March 7, 2019

The outlook iOS app is actually pretty good about bringing in google calendars, but not sure if you can do this without also linking a google email account.
posted by q*ben at 6:47 PM on March 7, 2019