It would be good to find a way around the planning fallacy, since never finishing your to-do list is a joyless way to live, and underestimating task-times means constantly rushing to finish things. (I speak as an expert.) How, though? Intuitively, it feels sensible to work out in detail what your projects involve, to break them into chunks and estimate how long each part will take. But the problem with unforeseen delays is you can't foresee them, no matter how finely detailed your planning. And so, writes Eliezer Yudkowsky on the Oxford University blog OvercomingBias.com, the 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. "You'll get back an answer that sounds hideously long, and clearly reflects no understanding of the special reasons why this task will take less time," he writes. "This answer is true. Deal with it."
In a 2008 column for The Guardian, Oliver Burkeman wrote about the planning fallacy and Douglas Hofstadter's Law. I was reminded of the column because during the past few weeks I've had many conversations with co-workers and interns about producing and project managing. During those conversations I've tried to emphasize the fact that planning is merely guidelines and the key to being the person responsible for making things happen is to adapt very quickly. In the coming week's I'll be exploring more on the subject of planning, projects, to-do lists and deadlines. In a way I'll be thinking by writing as I attempt to codify the working habits and not so mild obsessions that drive how I produce.