How Do You Manage Your Calendar and Not Let It Manage you!

How do you manage your calendar and make it repeatedly successful? Calendar management seems to be a common issue for all people, not just busy executives! With the availability of calendar apps today, even school students are keeping a calendar. But, wouldn’t it be nice if your calendar was a place of comfort and success, not a place of stress and broken commitments? I hope sharing a few of the processes that I use every week will help you get to a place of comfort and success!

Above view portrait of stressed young woman lying on floor surrounded by art supplies and designer work, copy space

Many of the tips and processes that I reference are widely available from books like Getting Things Done [i], The Four Hour Work Week [ii], and The 7 Habits of Highly Effective People[iii]. I have taken parts of many systems and put them together to make a system that works well!

I am not a believer that any system will work perfectly for everyone. However, if you can take one or two items from this article to help you, you have succeeded. As mentioned above, I have taken parts of many systems to create my system. Also, everyone has good weeks and bad weeks! Some weeks I do not even get a chance to complete my calendar, which is fine; it shouldn’t mean that you give up! Any system that you use is merely a set of tools to help you get back on track. We probably spend most of our lives off track! The difference between the successful people and the less successful is the tools and knowledge to get back on track! Once you have a system that you are comfortable with, stick with it. When you fall away from the system, come back and get things in order. It is a continuous process!

Frequently Asked Calendar Questions:

Should I keep separate digital calendars for different parts of my life, IE…home, work, kids? Unless your company has rules against keeping personal appointments on your company calendar, the answer is no. You should keep all digital calendar items in one place. If you have multiple calendars, you prolong the weekly review and create the potential for missed appointments and confusion. You may have noticed I said digital calendar, we will get to paper calendars later, but it is okay to keep an additional paper calendar.

The next logical question with anyone staying up to date in the latest tech is: Which is the best platform? How do I get my calendar to show up on all my devices? All the different platforms available are a source of frustration and endless calls to tech support for many, with new devices coming out quarterly! However, for a large share of people, if you are using Microsoft Outlook, there is an app for all mobile devices to keep your Outlook calendar on all of them.

If you are starting to use digital assistants such as Google Home, Alexa, or any others, there are some easy ways to get them to look at and copy your calendar. The first question is, do you need your calendar available to this device? If you used it to listen to music only, I wouldn’t go through the trouble of setting it up. If you must have your calendar available, I suggest the following.

  • Microsoft Flow has some good widgets that will sync your calendar.
  • You can also set up an Apple calendar to sync with your Outlook calendar.
  • I would limit the input of new calendar items to your tablet, phone, and computer. 
  • Should I share my calendar with others, and if so, should I share the details of appointments? You want to share your calendar with others that you work with. I would also suggest you allow them to see all details! If you don’t let others see the details, they will not take your scheduled events seriously. If you have something on your calendar that you don’t want others to see, mark it private. By trusting others with access to your calendar, they will automatically, in most cases respect it, and not schedule over your scheduled appointments.

I would also suggest that you share your calendar with your family and others who may want to know your schedule in the future. Sharing can save a lot of headaches with spouses and family members!

  • Should I put all my tasks in my digital calendar? The answer is no. Digital calendar should be for appointments only and reminders of date-specific things such as birthdays, anniversaries, Deadlines, etc. we will talk about the week view paper calendar later, but this is where you put your task! If you are sharing your calendar with others, you may, however, block time in the calendar as project work, so they do not schedule anything for you at that time. If you keep to these rules, others who have access to your calendar will be more likely to respect your appointments and know they are appointments!

Process for weekly calendar success

Now let’s talk about the process of how to prepare your calendar for the week correctly. Yes, I said the week. I have found it less stressful to schedule one week rather than a day at a time. Some of you will say that it is too hectic where you work to do this. But, give it a try for a month and see what you think. It is also much easier to see where to drop in items that come up during the week if you are looking at the entire week view. 

  1. Go through your updating process and make sure that your digital calendar (this should be appointments only) is accurate for the upcoming week. Now transfer this information to your weekly paper calendar. Yes, you are using that pencil and paper.
  2. Take some time to identify your roles in life. Once you identify your roles, they will not change a lot, but you need to look and adjust as required from time to time. These are the roles that you actively have in your life today. Here are some common examples: Work; CEO; Father/Mother; Son/Daughter; Board Member; Mentor; Church member; Volunteer; Hobbies; etc.

You will now list your roles on the right-hand side of the calendar. You may want to let a few rows between each for a related task.Many people skip this step in preparing for the week. This step helps me to make sure that I am not neglecting a portion of my life. It is effortless to concentrate on work and the non-profit board event you have coming up for a month. You have an angry family at the end of the month because you have not given them any quality time. Knowing your roles is an easy way to avoid that, or if a conflict with a role has to exist, at least you are aware of it! If you are aware, you can make other efforts to talk about it beforehand rather than after the fact. We all live busy lives, but it will be much less stressful if we know that we will have a busy couple of weeks and set that expectation with our family and other roles ahead of time.

  • Now take your list of tasks and identify the ones you need to make progress on over the upcoming week. (I am assuming at this point that you have a system for tracking your task, if not, refer to David Allen’s Getting Things Done) I use the Eisenhower Method 4 Quadrants to decide what the priorities are over the next week. Once you have that list, look at each and ensure that they are all tasks you must meet? Can you delegate any of them? Once you have the final list, place them under the proper roles they belong to. This exercise will help you see if you are skimping on time to any of the roles. For instance, if you have no family items listed for the week, you now have time to correct that and add something in there that will be meaningful for that role!
  • Now you will take the task you have identified and start putting it on the calendar in available time slots. You can very quickly see how your week will probably shape up and if you even have time to get all these items done. The most significant part of this exercise is to be realistic. You may also realize that a meeting or appointment doesn’t require your presence or could be rescheduled. During the process, I also try to make sure that I have some transition time between items. If every line of the calendar is complete, you will not get it all done. I also recommend using a pencil. The ability to erase allows for quick changes on the fly. 

This calendar now sits on my desk for one week, and I refer to it throughout each day to see what needs action next. At the end of the day, if something doesn’t get done, there is nothing wrong with moving it to another time slot. Your calendar should not work for you, and you should perform your calendar! I also know at the end of the week how I have tracked with my different roles. If I do not get family things done this week, I may plan something special for the following week. Unfortunately, you will have weeks that are all one role or the other, which does not allow time for the others. If you are aware of this, you could recognize and try to make changes for the coming weeks. Hopefully, you will be calm and productive after trying a few of these things!

[i] Getting Things Done: The Art of Stress-Free Productivity

Author: David Allen 

Getting Things Done: The Art of Stress-Free Productivity

[ii] The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich

Author: Timothy Ferris

The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich


[iii] The 7 Habits of Highly Effective People: Powerful Lessons in Personal Change

Author: Stephen R. Covey

The 7 Habits of Highly Effective People: Powerful Lessons in Personal Change

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