How to Catch Up With Your Calendar

If you’re like almost everyone I know, you probably have more on your plate than any one human being should.

If you’re fortunate enough to have some basic training in the area of personal productivity, you probably have some tools you rely on to help you manage, or attempt to manage everything on your plate.

Hopefully, one of those tools is a trusty calendar. I cannot stress enough, the vital importance of this one particular tool. In fact, I wrote about it in depth a few weeks ago, so check out this link if you want to know more about using calendars.

In reality, while calendars are an indispensable tool for collecting and displaying tasks in time, I find that many people in leadership have trouble keeping up with what they have scheduled each day, to the point where their calendars actually stop representing the allocation of time, and start functioning as elaborate to-do lists instead.

It’s easy to tell when this kind of thing happens. The tell-tale sign is a calendar completely filled up from dawn til dusk, with far more scheduled than what actually gets done each day. In this kind of environment, tasks and appointments are getting constantly rescheduled because there isn’t enough time. Unanticipated phone calls and emails occur as unwelcome intrusions. There’s a persisting sense of overwhelm and exhaustion, and even though the workday keeps getting longer, there’s never enough time.

Under these circumstances, the calendar merely suggests what might have been. No matter how much work gets done, there is always way more to do than time will allow, and the calendar ends up holding the balance of all that remains undone…a glorified to-do list of impossible length.

If all of this sounds familiar, listen up now. It doesn’t have to be like this. In fact, at a certain point, it has to be some other way. No one can operate at the top of their game for very long in this kind of environment. If you want to be as productive as you can be, you have to figure out how to catch up with your calendar.

In order to do that, you have to start using your calendar in a way that’s consistent with its purpose. Remember, your calendar is there to help you allocate your time. The purpose of a calendar is to help you manage the allocation of your time in such a way that you can stop worrying about what you need to do and when you’ll get it done.

Think about that. How would you have to relate to and use your calendar if you were serious about never being worried or stressed about what there is to do and when you’ll get it done? It really is possible, but for most people it requires a radical shift in their relationship to time.

The trouble with most of us is that we avoid confronting the totality of ALL the things we have to do, and ALL the time it takes to do those things. As a result, we underestimate how much time things actually take. We schedule our time without allowing for interruptions or unexpected problems. We put in our calendars all the things we wish we could get done, or think we should get done, but not everything we actually do.

In order to catch up with your calendar, you have to start allocating time for everything you actually do each day, and you have to be realistic about how much time you have, and what you can really expect to get done.

Here comes the hard part. If your calendar is completely overwhelmed with stuff to do, and you feel like you can’t keep up with it, you’re going to need to stop and reschedule. That’s right. Even though you don’t have enough time to sneeze, and you’re completely overwhelmed as it is, you’re going to have to carve out the time it takes to re-evaluate what’s on your plate and reorganize your calendar so that become a useful tool again.

As hard as it may be to imagine taking the time to do this, you have to remember that the longer you operate with your calendar the way it is, the more your productivity, not to mention your health and peace of mind, will suffer. Catching up with your calendar requires a distinct break from the normal routine. I recommend scheduling an entire morning or afternoon to sit down and do this work.

Start by making a list of all the things that aren’t getting done. Then, make a list of all the things you do that aren’t in already in your calendar. Next, carefully consider how much time it takes to complete each of these items. Then, start allocating blocks of time in your calendar to complete these tasks.

The most important part of this process is forcing yourself to confront the totality of all there is to do, and all the time it takes to do all of that. If you’re doing this effectively, you may notice your work stretching out over a larger period of time than you previously allotted. For example, what used to take up a week in your calendar may now take closer to two. Or, after allocating time for reading, responding to, and filing away email each day, you may realize that you’re completely booked for the next three weeks. It may become necessary to think carefully about how you prioritize your work.

While this may seem discouraging at first, it’s actually very good news. These are signs of a schedule that’s effectively and realistically managing the allocation of your time. It may seem like you’re planning to be less productive, but this is not the case at all. In fact, you’re planning to be as productive as you actually are, vs. planning to be far more productive than is humanly possible, and constantly struggling to keep up with an impossible work load.

Over time, you can fine tune and adjust your calendar so that it becomes a more and more useful tool, but the key is always to allocate sufficient time for all the work at hand, and to prioritize the work accordingly. Catching up with your calendar is not only possible, but fairly easy as well, and the results are well worth the work it takes, so what are you waiting for? Here’s to your productivity and peace of mind!

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