I've been testing both free and paid solutions to this problem for several years. I could duplicate my personal calendar events onto my work calendar, making them "private," but that's frankly just not a good idea - and most companies frown on it. Do I need to leave work right at 5:00 to ferry a child to soccer practice? If so, don't set up that 4:30 meeting. I frequently need to be able to see both my work calendar and my personal calendars side-by-side, so I can check for conflicts. Here's my real-world need: My wife and I maintain Google calendars for various purposes, but one primary calendar is the family calendar that keeps track of school events, appointments, practices, exams and so on for our children and ourselves. But changes you make with Outlook will not be reflected in your Google calendars. Changes made in Google Calendar, for example, may update in Outlook. The problem many users face is syncing those calendars for updates, especially bidirectionally. The Outlook client can open several types of calendars, and it does an excellent job of displaying an overlay view of multiple calendars. So, it's somewhat surprising that the calendaring function in Outlook 365/Outlook 2016 for Windows has almost no facility for two-way syncing with anything other than another Exchange-supported Outlook calendar. Microsoft Outlook is a complex, multifunctional software package, jam-packed with options and features.
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