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Antifragile Planning: Optimizing for Optionality (Without Chasing Shiny Objects)

taylorpearson.me · 4,036 words · saved by 3 readers

If you “have optionality,” you don’t have much need for what is commonly called intelligence, knowledge, insight, skills, and these complicated things that take place in our brain cells. For you don’t have to be right that often. All you need is the wisdom to not do unintelligent things to hurt yourself (some acts of omission) and recognize favorable outcomes when they occur.

Planning timelines have been getting shorter and shorter across every industry over the last couple decades. Companies that used to make ten-year plans now make five-year plans. Companies that used to make five-year plans now make three-year plans. Slowly, individuals and organizations are giving up the Luddite Hope – “that it is possible to enjoy the benefits of non-zero-sum innovation without giving up predictability.” My personal shift and revised process was driven by a practical need to resolve the inherent contradiction at the heart of the Luddite hope: focus and optionality . How

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