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Like many people, I sometimes have a conflicted view of deadlines. I can’t decide whether to despise them or to abhor them.  Of course I understand their place in any well-run workplace.  By placing temporal limits on tasks, they foster efficiency, finality, and the effective division of labor.  On the other hand, even when used properly, they generate stress, friction, disappointment, ulcers, heart attacks, and workplace violence.  It is a thin, wavy line between “deadlines” and “deadliness”.

Over the years I have developed some strategies to help minimize the stress of approaching deadlines.  Nothing complex or radical; just basic strategies that you might read in dozens of basic personal time-management books.  Using a calendar, making to-do lists, prioritizing (while keeping in mind the distinction between “urgent” and “important”) – common-sense things like that.  It has all helped, in increments.  But as I feel I have gotten better at managing deadlines, I have also discovered what I think of as “The Deadline Paradox”.  (Not to be confused with a Ludlumesque spy novel, which in any case would be called “The Paradox Deadline”.)

This is the Deadline Paradox: If I am not invested in a particular project, I end up stressed as the deadline approaches, because it is hard to be attentive enough; but if I am invested in a project, I still end up stressed by the deadline, because it is hard to feel like I am being attentive enough.

Say I’ve promised to deliver a memo by the 16th on a bland and difficult topic.  Whatever planning I do or time I set aside for the project, it will be hard to move forward on it as quickly as I might on another project, because I just can’t get into it.  A big chunk of what needs to get done may still be there as the deadline looms. But what if the topic is something I find totally inspiring, something I love working with and I know I can handle well? Then I dive into the project from day one, but get so totally involved – and become so perfectionistic – that I always feel like there is more to be done to improve the final product, even when it is time to move on.

Of course, the real world is not binary, either/or; sometimes a project falls in the middle of the spectrum, and these are often completely non-stressful.  But, with respect to the extremes, I have come to accept that I can’t just rely on project management techniques; I also need to look to the brute force of willpower and attitude adjustment.  Ironically, this is harder for me on the projects I love than on the projects I hate.  It’s more difficult for me to tell myself to stop working on a project that I am totally involved in, when I know I could improve it just that tiny bit more, than to force myself to turn my attention early on to something boring.  Perhaps that’s just because I seem to have had more practice with the latter.