In this conversation, Daniel L. Garner introduces us to the core distinction for his course “Look at the Birds of the Air” between planning and preparedness. Garner emphasises that one must be prepared because one cannot plan for everything, and that preparedness helps us deal with disruptions of plans, where planning by itself can turn into a system that becomes reified and mechanical and dead as opposed to live to the contingencies of life. While we need plans, and they are practically necessary, it is only when we shift to a mode of preparedness that we become anti-fragile because your plans inevitably fall at a great enough interval to a prediction horizon. We conclude with some thoughts on the disabling aspect to plans and the necessary context to understand preparedness in the face of technological singularity.