The Realistic Planning Paradox

When we say something does or doesn’t go ”as planned” it often means as assumed. We overcomplicate the planning of strategies, projects, programs, crises, or startups by making our planning assumption-based.

The paradox of realistic planning is that planning is simpler when it is realistic. Realistic means aligned with reality. Reality has two dimensions: the handful of things we know for sure and the vast, infinite space of what we don’t yet know — our uncertainties.

Our uncertainties are most accurately expressed as questions. Realistic planning is question-based planning.

Uncertainties include our assumptions and ambiguities. Assumptions are guesses, speculations, and opinions. Ambiguities are things that are unclear, unconfirmed, or undecided. In realistic, question-based planning, we turn uncertainties into new, actionable questions, new, actionable questions into actions, and actions into results.

Question-based planning always works because we always get answers to our new, actionable questions. Assumption-based planning doesn’t always work because we can’t always prove our assumptions are accurate predictions of the future. Prediction is tricky business in a universe where the future is intrinsically unpredictable and shapable.

Assumption-based planning can be seductive, especially if it is our only learned planning option. It is easy to have guesses, speculations, and opinions about any future situation or scenario. These can show up in the forms of hopes, concerns, and expectations. If our planning model is translating uncertainties into assumptions, we work hard to try proving our assumptions right.

Assumption-based planning is more complicated because it adds extra steps we don’t have in question-based planning. We form assumptions, take actions that don’t’ quite get the results we want, and repeat the actions that yield the same results. Assumptions don’t work because they are how we imagine reality is rather than how it actually is. They are prediction-errors.

Question-based planning works because it doesn’t work from possibility-limiting predictions. It works from possibility-expanding questions. While assumptions keep us going in circles, questions take us somewhere.

It is through the interest, curiosity, and wonder of being uncertainty-based that keeps us aligned with reality. Being realistic makes things much simpler.