Someone once asked me, “Are you organized inside your head, too?” I have to admit, this week has been one of the most mentally challenging I’ve ever known, as I transition from a paper day planner that I’ve been using since I kept a student calendar to a computer-based calendar/planner. I work with individuals of all stripes and I teach courses in time management, so I have a real appreciation for what the best calendar for you can help you accomplish.  Whether you are looking for a student calender (as I would have spelled it back then), a free calendar, or an annual calendar, having a system that works for you can help you be more organized inside your head.

If I was supposed to return your call this week, I’m working on it.

Loyal followers might know that I’ve just upgraded from my six year old computer to a new desktop and MS Office 2010. Let’s just say things are not going smoothly. But I have gone ahead and loaded all of my appointment and commitments into the calendar and begun syncing it to my iPad. After six hours of heads down conversion time, my Outlook program where my mail lives was operating unreliably. It was randomly deleting messages and data. EEEK!  After 12 hours of tech support, we think it’s working correctly, but there was one heart-stopping moment when my calendar info disappeared.  We were able to retrieve it and massage it back to behaving.

Using the free calendar on your phone isn’t revolutionary, but having it sync properly and having business-level reliability is important and harder than it sounds.  Keep reading for a good tip.

Pros for an Electronic Monthly Calendar:

• It looks more professional than paper.
• It comes with my computer and phone, and so it is a free calendar.
• It allows loading recurring events like monthly and weekly meetings and birthdays just once.
• It allows using different colors for different categories, like the family calendar and work appointments.
• It can be loaded on my desktop but stored “in the cloud” and accessed from any computer or mobile device, theoretically. (See more below.)
• It allows dragging emails over to a calendar and creating appointments almost effortlessly.
• It allows for easy scheduling of appointments with others via formatted email requests.
• It plays audible alarms.
• It can integrate with Outlook’s task list allowing me to link an email and an action item.
• It it an annual calendar, but doesn’t need to be ordered each year.
• If stored in the cloud, it can not be lost like a paper day planner.
• It allows sharing my calendar with a family member or coworker.
• It automatically overlays conflicting appointments, showing a schedule snafu quickly.
• It allows word searches within the calendar.

Cons for an Electronic Monthly Calendar:

• It takes longer to type in details of a meeting or task than it does to pencil a note in a day planner.
• You must enter details exactly right (am vs pm, next month vs. this month) or the appointment floats somewhere I might not have intended; these errors seem to be easier to make on the computer.
• I am terrified that it will crash or disappear. Backup is important.
• It is not easy to archive a copy with my tax records unless I print it off.
• Outlook 2010 features are much improved over what was available in Outlook 2003, but things can only be modified so far.
• I can only see four events per day in monthly view. Oh, if only real life had a limit of only 4 appointments per day!!!
• I must have an electronic device charged and with me to access my calendar.
• Each device shows a slightly different view of my monthly calendar. For instance, the iPad does not show all of the color coding that I set up on my desktop.
• I must sync at least daily to have a current copy of my calendar on my mobile device. (Read more below.)
• I’m very used to having a copy of my calendar open on my physical desk while I work, and I’m finding it disturbing to not have that. Yeah, I can keep a window open on my desktop, but it’s not the same thing.

To Do Calendar List

One of the major tenets that has made my best calendar systems work so well over the years is that the paper calendar, to do calendar list, and a subset of often-used contacts always always always travel together. As of now, my calendar is online, my contacts are still in the process of getting migrated and synced, but the to do calendar feature in Outlook leaves much to be desired. I’ll update you later this month with how I’m addressing that.  Generally I believe a to do list separate from your actual calendar works best for most people.

Best Calendar

The best calendar, bar none, is one that you have with you all the time.  A paper calendar will work if you carry it, but an electronic calendar will work, too, if you always have your phone along.  One cool little tech tip…if you do use an Outlook calendar, you apparently can sync it with your mobile device over the air automatically either using Google or one of the apps made for this purpose. It looks like Google Sync is for single users and Google Apps Sync is for companies who need to link up calendar and email systems for employees. Here’s a video that explains how this works. I’ll be setting this up before the month is out.

There are also other apps available to handle different platforms and vendors, so do a search for “sync calendar with xxx” where xxx is your device. I’d love to hear what works for you. Please comment below and share it with our readers.

One last thing…you absolutely have my permission to stick with a paper day planner if you chose, but DO have a calender/calendar/planner of some type if you want to be organized inside your head.