This chapter addresses the planning fallacy and the idea that we can plan the timescale of our daily activities. The law, named after cognitive scientist Douglas Hofstader, states that every task takes longer than we anticipate. Burkeman finds that this is the case no matter how much time we allocate, showing that time cannot be controlled.

Burkeman comes from a family of obsessive planners, who like to feel some sense of control over how the future will unfold. This may stem from his Jewish paternal grandmother’s trauma-response to the sense that she was lucky to leave Germany on time before the worst of Hitler’s antisemitic atrocities took place. Quite understandably, this matriarch passed onto her descendants the anxiety that if you did not plan things perfectly, catastrophe might occur. In a safer era, Burkeman models his grandmother’s attitude in actions such as leaving an exaggerated amount of time for airport departures.

However, being so emotionally invested in the belief that we can control the future often creates anxiety, as “the obsessive planner […] is demanding certain reassurances from the future – but the future isn’t the sort of thing that can ever provide the reassurance he craves” (115), given the uncertainty inherent in it.