On Planning

What is "On Planning" about?

Opening with Mike Tyson's line about everyone having a plan until they get punched in the mouth, Gilad challenges the illusion that careful planning can eliminate uncertainty or guarantee a predictable path, arguing that this belief keeps people stuck chasing an impossible level of control before they're willing to begin. He reframes the purpose of planning: not to remove surprise from life, but to prepare a person to execute, adapt, and keep moving once reality inevitably diverges from the plan. The essay introduces a visualization exercise in which readers imagine their ideal future as a documentary—describing in vivid, concrete detail how they move, what has changed, and what success looks like, as though it has already occurred—then work backward to identify essential milestones, breaking them into weekly and daily actions. Gilad insists the work should begin immediately, 'not when it feels perfect,' while staying flexible as reality unfolds. He closes by distinguishing the goal of planning from blindly following a fixed plan: real planning builds the capability to adapt and arrive despite uncertainty, rather than promising a smooth, uninterrupted path.

In brief

What are the key takeaways?

1. 01Planning can't eliminate uncertainty—its real purpose is to prepare you to adapt once reality diverges from the plan.
2. 02Visualize your ideal outcome vividly as if it already happened, then work backward into weekly and daily actions.
3. 03Begin executing immediately rather than waiting to feel ready or for the plan to feel perfect.