How do you handle this calendar issue?

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An executive secretary to the CEO of a fortune 50 company handles his calendar. When he has something due, a paper or a project, she enters the due date on his calendar. Then, she asks the executive how much time he needs to complete the project once he begins. If he says, “two weeks,” she records a date on his calendar two weeks before the due date, reminding him to begin the project.

Okay, due dates and start dates. Nothing new here.

She takes it a step further. She asks her boss how much prep time he estimates he will need before he begins the project—to do research, talk to people, gather his notes, and so on. If he says he needs a week to do that, she calendars a date one week before the start date, reminding him to do the prep.

One project, three dates in his calendar.

I like this. It allows the executive to do other work without having to think about the project until his calendar tells him to. In the past, I’ve calendared start dates and due dates but never a “prep” date.

Maybe I should try this?

Then I remembered that I’m not very good at estimating how long many projects will take. I also remembered what has happened to me in the past when I’ve scheduled start dates and due dates. Too often, they don’t stick and I wind up moving the dates, sometimes repeatedly, and my calendar becomes a mess of unfinished (and unstarted) projects. It makes me feel out of control, which is the opposite of what was intended.

No bueno.

I use a more fluid system now. Unless there is a fixed due date for a project, I start when I’m ready to start and finish when I’m done. I think a little more structure might benefit me, however, but I’m not sure what to do.

Should I calendar prep, start, and due dates for projects that are amenable to this but eschew it for others? Should I try to force myself to get better at estimating how much time I will need, and better at sticking to those estimates?

How about you? What do you do about calendaring projects that don’t have a due date assigned by the court or someone else? What do you about estimating how long a project will take? Do you use a different system?

I welcome your thoughts.

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