I have a desktop computer, a laptop, and a iPhone.  I frequently add meetings to my Outlook calender on my desktop computer, but sometimes enter them on my laptop.  And I frequently use my iPhone to alert me about upcoming meetings.  These leads to a major problem in keeping all three in sync.  Well, the best solution I have found to keep them synced is by using Google Calendar Sync (download).  Install this on both your desktop and your laptop (making sure to choose the 2-way sync), and then follow the steps from Setting up Google Sync with your iOS device.  From then on, the calendars in Outlook on your desktop, Outlook on your laptop, your iPhone, and Gmail will all be in sync.  So no matter which one you use to enter a meeting, all the others will be updated in seconds.  Of course, this requires you to have a Gmail account, but they are free and you can continue to use your current email account and just use the Gmail account for your calendar.

Some other notes about this solution:

• You can always go to your Google calendar if your desktop and laptop are not available
• A cool thing about Google Calendar is it will add a map link to addresses that you have listed in appointments
• Note that this is syncing my personal Outlook calendar.  My business Outlook calendars are already synced because they use Microsoft Exchange and therefore each have their own calendar that is available under “My Calendars”
• There is a bug where appointments don’t get synced if they were created before you installed the Google Calendar Sync (you must delete and recreate them)
• Go to your contacts on Gmail and enter birthdates so they show up on the calendar
• On Google Calendar, add the US Holidays calendar (see How to Add Public Holidays To Google Calendar).  Also add the “Contacts’ birthdays and events” calendar
• To add holidays to Outlook, see Add National Holidays in Outlook Calendar
• Contact’s birthdays or US holidays don’t get copied from Google calendar to your Outlook calendar unless while in Google calendar you choose “copy to my calendar” for each item and set to repeat yearly (a pain!)