[T]he problem with unforeseen delays is you can’t foresee them, no matter how finely detailed your planning… [T]he unlikely trick is to plan in less detail: avoid considering the specifics and simply ask yourself how long it’s taken to do roughly similar things before.
[…]
Better yet, where possible, avoid planning altogether. Use the “ready, fire, aim” approach, and correct course as you go along.
Oliver Burkeman on the psychology of why everything takes longer than you think.
Also see Frank Partnoy on the art of delay.
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