The trouble with deadlines: A conceptual analysis and alternative proposal

Dear Philosophical Friend,

By means of philosophical inquiry, we determined what would be an appropriate deadline for the project you wish to complete. Specifically, we asked three questions that were based on the gift economy worksheet:

1.) Is it a generous deadline and will allow for surprises?
2.) Is it urgent enough to avoid squandering my time?
3.) Will I be able to complete my project in a way that is aligned with certain salient virtues?

Since we came to the conclusion regarding a suitable date (that is, one to which you could answer affirmatively all three questions), you write that some things have changed about this project and some surprisingly good things have happened at the place you work. The first, therefore, is coming along more slowly than you had anticipated, and the second is an unexpectedly timely opportunity that is requiring more of your attention. You conclude that it is no longer possible for you to answer the third question in the affirmative: that is, with a wholehearted Yes.

You have written, then, a beautiful inquiry into the appropriateness of the deadline. The puzzle that concerns you is how it is possible to modify deadline P and at the same time to show that you are the kind of person who can demonstrate that you can consistently meet deadlines. It would seem that one thing–the resetting of the deadline or the dedication to meeting the deadline–would have to give. However, neither conclusion seems palatable. On the one hand, if you meet the deadline in this case, you will have failed to exercise other salient virtues about which we have spoken, thus telling against some other features of your character. On the other hand, if you modify the deadline, then you won’t be able to hold onto the claim that this exercise will be a demonstration of your ability to set an appropriate deadline and stick to it.

In light of this dilemma, you are considering the first possibility–namely, extending the deadline so that it accords with what is appropriate. You ask whether you have reasoned things through well.

*

I have come to think that perhaps we have made an error from the very beginning. I have been thinking further about the principal assumption we are making. This is that we are setting and meeting deadline. We take it for granted that P is a deadline rather than some other kind of thing, and from here we inquire further into setting and meeting. Let us consider this assumption further by asking what a deadline is and whether it is a requirement to speak and think in these terms.

The starting point of my inquiry into the nature of a deadline was to consult the Oxford English Dictionary.  A deadline, we read, is ‘a line that does not move or run.’ Definition 1a comes from military discourse: ‘a line drawn around a military prison, beyond which a prisoner is liable to be shot down. orig. U.S.’ One example comes from the Civil War: ‘Seventeen feet from the inner stockade was the ‘dead-line’, over which no man could pass and live.’

A deadline is a line that is posited over there beyond a certain safe zone. It is not to be moved or fudged with and not to be crossed over or transgressed. In these respects, it differs from other kinds of lines. There are lines we walk along when we queue up. And there are starting lines and finishing lines. Concerning races, the starting line is the point from which one departs while the finishing line is the point beyond which one aims to pass. One wants to ‘get to’ the finish line. But one has no desire to ‘get to’ a deadline or to ‘stand on’ a deadline. It is rather something to be set beyond the range of one’s activities, undertakings, and tasks. But with what view in mind?

The example included above seems to tell us something further about the motivating force of deadlines. One can imagine activities taking place ‘before’ a deadline: A delivers a package to B under the vigilant eye of the looming deadline. What motivates A to deliver this package to B? Apparently, he does not want to cross the line. Thus ensues a dilemma concerning his motivation:

1.) Either he delivers the package before the deadline, or he does not.

2.) If he succeeds in delivering the package before the deadline, then he is relieved (of a burden).

3.) If he fails, then he is penalized.

 What is assumed in this scenario about human motivation is that, first, qua agent he stands either to fail or to succeed and, second, he believes that he must be motivated by fear. A deadline, then, is not to be approached (as a finish line is) but rather looms in the distance rather like a punitive god. In view of this looming being, he tells himself that he had better…, he must…, he ought…, and so on.

The further assumption is that deadlines are the sorts of things that are set and met. But to set a deadline is to try to say something final about our connection to the future despite the fact that such finality seems impossible. And so to meet a deadline may tell us more about our responsiveness to fear–about how well we respond in the face of fear–than it does about our ability to see something or other through.

*

We would like to know what a deadline is, and so far we have only examined the dangers associated with the concept of deadline. Let us examine this further.

(a) We wouldn’t say, for instance, that we set a deadline for the same day. Hence, a deadline appears to be something long-term.

(b) We wouldn’t set a deadline for members of our families or for friends. Hence, a deadline seem to be something concerning certain kinds of strangers: colleagues, business associates, fellow professionals, etc.

(c) We wouldn’t set a deadline on matters of the heart. (The date one gets married is, strictly speaking, not a deadline.) Hence, a deadline would seem to have to do with matters of business, broadly understood.

(d) We wouldn’t set a deadline on having a meeting (that is ‘scheduling’ a ‘date’), on simply having an idea, and so on. Hence, a deadline would seem to have to do with the things that are produced or delivered.

(e) We wouldn’t set a deadline on something that the other would find trivial or valueless. Hence, a deadline would seem to have to do with what is beneficial.

Putting these elements together, we could define a deadline as

  • a mutually agreed upon date secured by parties A and B, where A is to deliver thing X to B for the benefit of both parties.

Person A, seeking not only to secure a certain benefit, is motivated both by fear and by the desire not to appear untrustworthy or unreliable in the eyes of B. For A, things are very urgent (read: fraught). B, in turn, is motivated by the desire to do something with X. Receiving X before the deadline is an urgent (read: fraught) matter. This contractual situation hardly seems like the starting point of friendliness.

*

In light of these considerations, I believe that we began with an error in understanding, and this led us astray. Now, I am not at all sure that thinking in terms of deadlines is in tune with exercising the salient virtues and with testing one’s character in any appropriate way. But in saying this, it may seem as if we cannot learn how to hold ourselves gently to account. In response to this challenge, I want to say something far simpler and this in a Daoist key.

Let us suppose that A and B are beginning out of a basic sense of friendliness. A wishes to offer something to B; B would like to receive this offering. The offering would be offered in a timely, wholehearted manner. Perhaps, trying again, we can venture three gift economy reformulated questions:

1.) Timeliness 1. What would give A ‘just enough time’ for A to allow thing X to come into being?

2.) Timeliness 2. What would give B ‘just enough time’ to be able to amicably receive X and to do whatever further that B needs to do with X?

3.) Wholehearted Manner. How could A kindly go about allowing X to come into being and offering X to B in a way that it is wholehearted from beginning to end? If this were the case for A, could B receive the offering just as wholeheartedly?

It seems to me that these three questions are cast in a softer as well as more accurate light. Properly formulated, properly understood, and clearly answered, they alleviate the kinds of concerns and dilemmas that flow from thinking in terms of the concept of deadlines.

In philosophical friendship,

Andrew

(I am grateful to Aleksandra for helping me to think through this puzzle of deadlines.)

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