workfutures.io

workfutures.io

How To Use Time

Constructive Uncertainty

The world is complex, and we must find a balance between taking action and accepting uncertainty. Our natural impulse toward quick decisions misses out on a powerful tool: negative planning.

Stowe Boyd
Oct 09, 2025
∙ Paid
4
1
1
Share
yellow road signage at daytime
Photo by Robert Ruggiero on Unsplash

…

One of the paradoxes that reveals a great deal about making sense of the world is the tension between uncertainty and action. On one hand, we are often told that being effective relies on decisive reasoning, and quickly choosing a course to pursue even with incomplete information. However, opting to eliminate the discomfort of an uncertain or ambiguous situation by making a quick decision can often backfire, and in predictable ways.

When I recall events in my life where my decisions went sideways, they were often hurried, and driven more by my desire to end a period of stress and insecurity than actually determining what could go wrong… before finding out the hard way.


Share


And the world is more complex than ever, more ambiguous, less predictable. As Margaret Wheatley points out in Willing to Be Disturbed,

we live in a complex world, we often don’t know what’s going on, and we won’t be able to understand its complexity unless we spend more time in not knowing.

Wheatley’s formulation, that we need to spend more time in not knowing, is a first step in deconstructing uncertainty. One aspect of contemporary emotional maturity is to accept the state of not knowing. Not having a quick answer for complex questions. Being willing to admit being confused by new situations, or rapid changes in the context we are living and working in. Remaining open to spending more time listening to alternative viewpoints before shutting down gathering inputs. These are all aspects of constructive uncertainty, a term I learned from Howard Ross: ‘learning to slow down decision-making’.

The poet John Keats commented in a letter to his brothers that Shakespeare was able to accept uncertainty in his characters and their context, and coining the term negative capability to capture what he described as “being in uncertainties, mysteries, doubts, without any irritable reaching after fact and reason”.

So, too, we need to cultivate a negative capability in our approach to an uncertain world. All too often we approach decision-making or strategy formulation in an overly positive manner, which may have serious downsides. JP Castlin argues

Keep reading with a 7-day free trial

Subscribe to workfutures.io to keep reading this post and get 7 days of free access to the full post archives.

Already a paid subscriber? Sign in
© 2025 Stowe Boyd
Privacy ∙ Terms ∙ Collection notice
Start writingGet the app
Substack is the home for great culture