We can only connect the dots looking backward, so long-term plans should stay flexible

In his 2005 Stanford commencement address, Steve Jobs said that you cannot connect the dots looking forward; you can only connect them looking backward. He was talking about a personal career, but the idea applies to planning more broadly.

Looking back, a sequence of events appears orderly, even inevitable. Looking forward, it is uncertain. Researchers call part of this hindsight bias, the tendency to see past events as having been more predictable than they were. That makes it easy to overrate our ability to plan far ahead.

We think the lesson is not to give up planning, but to plan in a way that preserves options: take small, reversible steps, learn from each, keep some resources in reserve, and be ready to change direction when new information arrives. The Collingridge dilemma, which says that a technology is easiest to change early, when we know least about its effects, makes the same point from another angle.

What would change our mind: evidence that rigid long-term plans outperform flexible ones in conditions of high uncertainty.