Why do software projects fail?


In the Theatetus, Plato writes that ‘philosophy begins in wonder’.  Here is Jowett’s translation of the passage:

Soc: …I believe that you follow me, Theaetetus; for I suspect that you have thought of these questions before now.

Theaet. Yes, Socrates, and I am amazed when I think of them; by the Gods I am! and I want to know what on earth they mean; and there are times when my head quite swims with the contemplation of them.

Soc. I see, my dear Theaetetus, that Theodorus had a true insight into your nature when he said that you were a philosopher, for wonder is the feeling of a philosopher, and philosophy begins in wonder. He was not a bad genealogist who said that Iris (the messenger of heaven) is the child of Thaumas (wonder).

In the Metaphysics, Aristotle continues the same theme (tr. W. D. Ross):

For it is owing to their wonder {ex archês men ta procheira tôn atopôn thaumasantes} that men both now begin and at first began to philosophize; they wondered originally at the obvious difficulties, then advanced little by little and stated difficulties about the greater matters, e.g. about the phenomena of the moon and those of the sun and of the stars, and about the genesis of the universe. And a man who is puzzled and wonders thinks himself ignorant (whence even the lover of myth is in a sense a lover of Wisdom, for the myth is composed of wonders); therefore since they philosophized in order to escape from ignorance, evidently they were pursuing science in order to know, and not for any utilitarian end.

This wonder tradition in philosophy has two principles. One is that wonder must lead to the articulation of questions, for without questions and dialectic, wonder never goes any further.  The second is that questioning must be non-utilitarian, and that its end must be contemplation, rather than the solution to a practical problem; in other words, questions must be open-ended in order to count as philosophical (i.e., pure scientific) problems.

Thus Aristotle continues, in Book II of the Metaphysics:

The investigation of the truth is in one way hard, in another easy. An indication of this is found in the fact that no one is able to attain the truth adequately, while, on the other hand, we do not collectively fail, but every one says something true about the nature of things, and while individually we contribute little or nothing to the truth, by the union of all a considerable amount is amassed. Therefore, since the truth seems to be like the proverbial door, which no one can fail to hit, in this respect it must be easy, but the fact that we can have a whole truth and not the particular part we aim at shows the difficulty of it.

Against this tradition, Descartes, an extremely practical man, argues in Articles 77 and 78 of Passions of the Soul (tr. Stephen H. Voss):

Furthermore, though it is only the dull and stupid who do not have any constitutional inclination toward Wonder {l’admiration}, this is not to say that those who have the most intelligence are always the most inclined to it.  For it is mainly those who, even though they have a good deal of common sense, still do not have a high opinion of their competence [who are most inclined toward wonder].

And though this passion seems to diminish with use, because the more one encounters rare things one wonders at, the more one routinely ceases wondering at them and comes to think that any that may be presented thereafter will be ordinary, nevertheless, when it is excessive and makes one fix one’s attention solely upon the first image of presented objects without acquiring any other knowledge of them, it leaves behind a habit which disposes the soul to dwell in the same way upon all other presented objects, provided they appear the least bit new to it.  This is what prolongs the sickness of the blindly curious — that is, those who investigate rarities only to wonder at them and not to understand them.  For they gradually become so given to wonder that things of no importance are no less capable of engaging them than those whose investigation is more useful.

Descartes found many ways to break with the Aristotelian tradition that had dominated Western thought for over a millennium, but none, I think, more profound than this dismissal of the wonder tradition.  In this brief passage, he places intelligence {l’esprit} above contemplation as the key trait of philosophizing.

A consequence of this is that the nature of philosophical questioning must also change.  In a Cartesian world, questions must have a practical goal.  Difficult problems can be broken down into their components, and if necessary those must be broken down into their components, until we arrive at a series of simple problems that can be solved easily.

Descartes’ position is only strengthened by what is often called the scandal of philosophy: why, given all this time, has philosophy failed to answer the questions it originally set for itself?

  • Does God exist? 
  • Is there life after death? 
  • Do we possess free will?
  • What is happiness, and is it attainable?
  • What is Justice?
  • What is Knowledge?
  • What is Virtue?

Another way to look at the scandal, however, is not as a problem of lacking answers to these questions, but rather as a problem of having an overabundance of answers.  Philosophy, over the centuries, has answered the question of God’s existence with both a yes and a no.  There are five canonical proofs of God’s existence, as well as a multitude of critical analyses of each of these proofs.  We are told that Occam’s Razor, originally a tool of theological discourse, demands that we reject God’s existence.  At the same time, we are told that Occam’s Razor, the principle that simple answers are preferable to complex answers, itself depends on a rational universe for its justification; for the only thing that can guaranty that the universe is simple and comprehensible rather than Byzantine in its complexity, is God Himself.

The scandal of philosophy is itself based on a presupposition: that this overabundance of answers, and the lack of definitive answers, is contrary to the purpose of philosophical questioning.  Yet we know of other traditions in which the lack of answers is indeed a central goal of philosophical questioning.

Zen koans are riddles Zen masters give to their students to help them achieve enlightenment.  Students are expected to meditate on their koans for years, until the koan successfully works its effect on them, bringing them in an intuitive flash into the state of satori

  • Does a dog have Buddha-nature?
  • What is the sound of one hand clapping?
  • What was your original face before you were born?
  • If you meet the Buddha, kill him.

I dabble in the collecting of questions, and with regard to this habit, the observation Descartes makes above about the curious “who investigate rarities only to wonder at them and not to understand them” fits me well.  One of my favorite sets of questions comes from Robert Graves’s The White Goddess, a book which, starting from an analysis of The Romance of Teliesin that makes Frazer’s Golden Bough seem pedestrian by comparison, attempts to unravel the true purpose of poetry and, in the process, answers the following questions:

  • Who cleft the Devil’s foot?
  • What song did the Sirens sing?
  • What name did Achilles use when he hid from the Achaeans in the women’s tent?
  • When did the Fifty Danaids come with their sieves to Britain?
  • What secret was woven into the Gordian Knot?
  • Why did Jehovah create trees and grass before he created the Sun, Moon and stars?
  • Where shall Wisdom be found?

Another set comes from Slavoj Zizek’s Enjoy Your Symptom!, in which Zizek elucidates certain gnomic pronouncements of Jacques Lacan through an analysis of mostly 50’s Hollywood movies:

  • Why does a letter always arrive at its destination?
  • Why is a woman a symptom of man?
  • Why is every act a repetition?
  • Why does the phallus appear?
  • Why are there always two fathers?

Modern life provides its own imponderables:

  • Paper or plastic?
  • Hybrid or Civic?
  • Diet or exercise?
  • Should I invest in my 401K or pay down my college loans?
  • Should I wait to get an HD TV?
  • When shall I pull out of the stock market?

There are no definitive right or wrong answers to these questions.  Rather, how we approach these questions as well as how we respond to them contribute to shaping who we are.  In his short work, Existentialism and Human Emotions, Sartre tells an anecdote about a student who once asked him for advice.  The student wanted to leave home and join the French Resistance.  The reasons were clear to him. The Germans were illegitimate occupiers and it was the duty of every able-bodied Frenchman to fight against them.  At the same time, the student had a sickly mother who required his assistance, and leaving her would not only break her heart, but he might possibly never see her again.  To leave her would entail sacrificing his filial duties, while not to leave her would entail abandoning his moral duty.  To this student, caught in the grips of a mortal quandary,  Sartre offered the unexpected advice: choose!

…[I]n  creating the man that we want to be, there is not a single one of our acts which does not at the same time create an image of man as we think he ought to be.  To choose to be this or that is to affirm at the same time the value of what we choose, because we can never choose evil.  We always choose the good, and nothing can be good for us without being good for all.

But this isn’t the whole truth.  There are also choices we make that appear arbitrary at the time, committed without any thought of ‘man as he ought to be,’ but which turn out to have irreversible consequences upon who we become.  In the film The Goalie’s Anxiety at the Penalty Kick, Wim Wenders follows a goalie who is kicked off of his soccer team after failing to defend against a penalty kick that costs his team the game.  The goalie proceeds aimlessly through a series of pointless and reprehensible acts.  I once asked a soccer-playing friend if the circumstances of the penalty kick are as they were described in the movie, and he said yes.  Before the penalty kick, against a skilled opponent, the goalie has no idea which way the ball will go.  He stands in the middle between the two posts and must choose which in direction he will leap, without enough information to determine whether his choice is the right one or the wrong one.  The only thing he knows is that if he does not leap, he will be certain to fail.

All these theoretical questions, and the survey of the theory of questioning in general, are intended to provide the background necessary for answering the very practical question:  Why do software projects fail?

Fred Brooks’s succinct answer to this is: software projects fail because software projects are very hard to do.  In other words, we are asking the wrong question.  A better way to phrase the problem is “Why are we still surprised when software projects fail?”

This question might be extended to other fields of endeavor:

  • Why are term papers turned in late?
  • Why do we fail to pay our bills on time?
  • Why do we lie when we are asked over the phone, “Were you sleeping?”

In the discipline of software development, it is often found as one item in a larger list of software koans:

  • Why do software projects fail?
  • Why does adding additional developers to a project slow the project down?
  • Why does planning extra time to complete a task result in no additional work being done?
  • Why do developers always underestimate?
  • Why are expectations always too high?
  • Why does no one ever read documentation?
  • Why do we write documentation that no one ever reads?
  • Why is the first release of any code full of bugs?

Here we have an overabundance of questions that can all be answered in the same way.  Kant phrased the answer in this way:

Out of the crooked timber of humanity, no straight thing was ever made.

Aristotle phrases it thus in Metaphysics II:

Perhaps, too, as difficulties are of two kinds, the cause of the present difficulty is not in the facts but in us.

3 thoughts on “Why do software projects fail?”

  1. "What name did Achilles use when he hid from the Achaeans in the women’s tent?"

    It’s not often Suetonius on the Grammarians is referenced on the internet. Actually, Hyginus has the answer to this one:

    "When Thetis the Nereid knew that Achilles, the son she had borne to Peleus, would die if he went to attack Troy, she sent him to island of Scyros, entrusting him to King Lycomedes. He kept him among his virgin daughters in woman’s attire under an assumed name. The girls called him Pyrrha, since he had tawny hair, and in Greek a redhead is called pyrrhos."

  2. Wonderful, Conrad. Thanks.

    Rounding out the story, Odysseus used a ruse to discover Achilles, son of Peleus. He placed a sword in the tent, and Achilles was unable to resist going over and admiring it, unlike the other young ladies; thus was he undone by his own warlike nature. Deidamea, one of the other ladies in the tent, bore Achilles a son, Pyrrhos, who later came to Troy and slew Priam (according to Virgil, though the dates don’t quite work out for me; Pyrrhos would be 10 at the end of the Trojan war, wouldn’t he?). On his return journey, Pyrrhos was in turn slain by Orestes, the son of Agamemnon, leader of the Argive army (himself slain by Clytemnestra), at Delphi. A Pyrrhic victory indeed, except that the phrase "Pyrrhic victory" is derived from another Pyrrhos, king of Epirus, who won his famous battle against the Romans in the 3rd century, B.C.

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