Is daily planning irritating you to no end? Is there a way to sidestep this exhaustion when planning?

You’ve probably heard it time and time again: plan your day in advance, you’ll save time in execution and you won’t have the struggle of constantly asking “what should I be doing right now?”

That’s all well and good. The problem is we automatically assume it’s simply sitting down and jotting down a list of tasks. We forget that other factors will appear and sap our patience more than the planning itself. 

However there are ways to avoid these factors. Planning is still an involved task, but there is no excuse to make it harder than it is. 

Let’s dive in to figure out how to remove these issues that make planning a chore.

Do you know the true origin of Chicago’s nickname “The Windy City”?

The immediate answer would be the weather of course. But this isn’t the case. Instead, it has to do with the people of the city!

Journalists in the 19th-century coined the term by referring to the Chicago residents as “windbags” and “full of hot air.”

This ties nicely with what we’re going to cover today which is daily planning. And why we find it so tedious to plan the day. We often think it’s due to the size of the tasks we are tackling or because of something that has to do with the plan itself.

But this is just like The Windy City story.

We make assumptions and think the name originated from weather. We just take it information as we receive it. These assumptions can wrongly direct us and limit progress. If we assume the process of planning itself is exhausting we won’t investigate how to make it better.

It could be something right on the periphery that has its hand in mucking things up. It’s not the planning itself. It’s about the other factors.

What are these factors?

The three things we’re going to cover on daily planning are:

1. The time you choose to plan your day.
2. How much time you spend planning.
3. And finally, the selection of tasks.

Let’s begin with the first one, which is when you are planning your day in the first place.

1- The time you choose to plan your day.

The best time to plan your day is the night before. The second best time is in the morning. At a distant third is planning when chaos has struck.

Planning the night before allows you to “sleep on” your tasks and problems. You’ll wake up with new insights. The second option allows you to gain perspective of your day before it is completely underway. The third option, when chaos has struck, is really just a last ditch effort.

We have an amazing tendency to try new ideas, get results, and then abandon the methods. We assume that we have it under control now. Daily planning is useful when you get in the habit of it. Then once demands for your time die down or tasks are handled appropriately you cast away daily planning. This is a mistake.

Are you planning when you’re forced to or planning based on regular cadence? Whether it’s in the morning or night, keep planning daily. This takes us to problem number two, namely the time you spend planning.

2- How much time you spend planning.

As Eisenhower once said, “a plan is useless, but the planning process is priceless.” Even the best laid plans will fail eventually. New information develops, obstacles appear, people fall through on promises. However, the very act of sitting down and working through your thoughts is the real value of planning. With that said, how much time should you spend on your daily plan? About 10 minutes.

If you are spending much longer than 10 minutes to plan your day there is a problem, or multiple problems, in your process. You may be unclear on deadlines or your tasks lists are scattered.

Another reason for long planning sessions is perfectionism. Spending a few hours will only have a very small impact on the quality of your plan. The difference between a 10 minute daily plan and a 3 hour daily plan is comically small. 

Remember, you are outlining the track you will run on. Save the strategizing power for projects and goals. A daily plan is simplify focusing your efforts for the coming day quickly.

This take us to the third part, which has been touched on a bit.

3- And finally, the selection of tasks.

This is the meat of your planning, and why daily planning is so frustrating. Without keeping clear track of your tasks you won’t plan. And when chaos strikes you’ll be grabbing a sheet of paper trying to plan something in the face of overwhelm. Then your planning process will be extended because you don’t know what you’re working on. 

Unclear responsibilities are the first domino in daily planning overwhelm. 

To start getting control of your selection of tasks, begin with a master list. This is the foundation of your time planning system. Write down everything possible that you will need to do for the indefinite future. Of course, this won’t include activities like eating or routines. As new ideas, goals, tasks, and responsibilities arise; write them down on your master list first. Don’t trust your tasks to memory. 

With a master list you’ll be able to pluck tasks so your daily plan is based on reality. 

Aim for a 10 minute daily plan at the end of every day. Maintain a master list and aim to spend 10 minutes on your nightly plan.