Perfectionist's Trap

Pursuit of perfection prevents completion.

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Four Thousand Weeks

Four Thousand Weeks

He might have been a genius, but he was also a perfectionist: the mosque of his imagination was perfect, and it agonised him to contemplate the compromises that would be involved in making it real. Even the greatest of builders would inevitably fail to reproduce his plans absolutely faithfully; nor would he be able to protect his creation from the ravages of time – from the physical decay or marauding armies that would eventually reduce it to dust. Stepping into the world of finitude, by actually building the mosque, would mean confronting all that he couldn’t do.
Leonardo da Vinci

Leonardo da Vinci

As Vasari explained about Leonardo’s unfinished works, he was stymied because his conceptions were “so subtle and so marvelous” that they were impossible to execute faultlessly. “It seemed to him that the hand was not able to attain to the perfection of art in carrying out the things which he imagined.” According to Lomazzo, the other early biographer, “he never finished any of the works he began because, so sublime was his idea of art, he saw faults even in the things that to others seemed miracles.”
The Perfectionists

The Perfectionists

H1, H2, and H3, each clock a subtle improvement upon its predecessor, each the work of years of patient experimentation—H3 took Harrison fully nineteen years to build—employ essentially the same bar balance principle, and when they are working, they are machines of an astonishing, hypnotic beauty and seemingly bewildering complexity.
Hackers & Painters

Hackers & Painters

The alternative approach might be called the Hail Mary strategy. Instead of getting a prototype out quickly and gradually refining it, you try to create the complete, finished product in one long touchdown pass. Countless startups destroyed themselves this way during the Internet Bubble.
Founders at Work

Founders at Work

And the people doing the second system are just too naïve; they haven't worked on this problem before, and they're young, maybe, and they just don't realize that it was hard. Fred Brooks said that the second system is always late; sometimes years later than you expect. And in fact, because of the ambition, usually it won't solve any of the problems.
The Inmates Are Running the Asylum

The Inmates Are Running the Asylum

Like mad sculptors chipping away at a huge block of marble hoping to discover a statue inside, the developers wrote immense quantities of useless code that was all eventually thrown away, along with money, time, reputations, and careers.
Coders at Work

Coders at Work

At the end of the day, ship the fucking thing! It's great to rewrite your code and make it cleaner and by the third time it'll actually be pretty. But that's not the point—you're not here to write code; you're here to ship products.
To Engineer Is Human

To Engineer Is Human

Other recognized masters often express the thought that they abandon a work rather than complete it. What they mean is that they come to realize that for all their drafts and revisions, a manuscript will never be perfect, and they must simply decide when they have caught all its major flaws and when it is as close to perfect as they can make it without working beyond reasonable limits.