Self Improvement · Uncertainty

Planning Pitfall

“The best-laid plans of mice and men are oft to go astray” ~ Robbie Burns
Burns seems to be saying “No matter how carefully a project is planned, something may still go wrong with it.” Yet in most situations, we ignore this sage advice and expect that ‘if we plan it, it will happen’. We imagine that there are no variables, external influences or unexpected providence that makes our certain expectation fallible.
My contention isn’t that we shouldn’t embrace expectations but rather that we should explore options that are as yet unimagined. Certainty creates a space where willful blindness rears its head and closes off alternatives. This leaves us ill-prepared and even surprised when something doesn’t turn out as we anticipated. When the unexpected leads to frustration, certainty is trying to bully us into mediocrity. If we lean into uncertainty, the unexpected nurtures curiosity and creativity.

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How do we get off the train? Just when we think that there is a breakthrough, we usually are chasing a desired outcome. Brainstorming quickly becomes stormtrooping. Once a destination is laid in, our planning GPS kicks in and we begin exploring the fastest, shortest, cheapest, most convenient route to victory. What if a few detours or roadblocks changed the route? What if the destination is not quite right?

Leaning into uncertainty isn’t easy or organic. Nothing really is. It requires a disposition to curiosity and a tenaciousness to breaking form. An intentional tendency to ask ridiculously difficult questions in order to understand is an asset worth pursuing and an optimistic wisdom to know when to stop asking will keep some semblance of planning alive for those who struggle with ambiguity.

To begin, it may be helpful to ask 4 whys. When you are feeling sure of the destination or next step, ask why. Why do we believe that growth is the most important metric? – however you answer that question, ask why again, 3 more times. What do you notice? Has there been an orientation shift? Are you still charging ahead? Was there an unexpected lesson? None of these observations are negative, they just are.

After trying 4 whys, move to the next step. If you get to a stage where you are blinded by certainty again, try 4 hows, or 4 whos …

Curiosity begets curiosity. Lean into uncertainty and see what you see.

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