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Desert Highway
Thoughtful writing authored and shared by members of of the Thinking Collaborative community to support others on the journey.

Sustaining the Journey

The Discipline of Will

Authored By:

Walter Basnight, Secondary Learning Coach for the American International School Chennai, India and member of the Thinking Collaborative Futures Team


January 28, 2019

Efficacy has been an important part of my success as a new coach and one that I continuously cultivate. In support of my increased efficacy, I have leaned on the work of Ryan Holiday, specifically his thoughts in The Obstacle Is The Way: The Ancient Art of Turning Adversity to Advantage. In previous posts I have considered the Stoic Disciplines of Perception and Action. This final post considers the Discipline of the Will.

The Discipline of the Will is the third critical discipline and the most difficult to cultivate. Holiday suggest that we can think, act, and, finally, adjust to a world that is inherently unpredictable. The Will is what prepares us to do so. It protects us against it and allows us to thrive in spite of it. He states, “If Perception and Action were the disciplines of the mind and the body, then Will is the discipline of the heart and the soul. Will is fortitude and wisdom – not just about specific obstacles but about life itself and where the obstacles we are facing fit within it.” (Holiday, 130)

In the development of this discipline, Holiday offers that misfortune, challenges, and uncertainty are a natural part of life. Taking the path of least resistance teaches you nothing. Instead, Holiday shares a list of practices that build one’s capacity to face obstacles. They include: Anticipation, Art of Acquiescence, Love, Fate, Perseverance, Selflessness, and Meditate on your Mortality.

As a coach, I have cultivated my ability to “anticipate” as defined by Holiday. This includes pre-thinking through the multiple ways an interaction may fail. While counterintuitive, anticipating failure, or attempting hindsight in advance, pays dividends. It is a technique coined by psychologist Gary Klein known as a ‘premortem’. Instead of reflecting on failures after the fact, you actively look for things that may go wrong before even beginning. Holiday suggests to always prepare for disruption because, more often than not, it will happen. Most meetings don’t go the way you intended, some are better than you thought and others miss the mark entirely.

It is my belief that this practice supported me in a failed meeting a few months back. The group I was facilitating quickly hit an impasse in the work and it was clear that we weren’t going to complete our objectives. This was okay as I was able to remain cool headed because I had anticipated something could go wrong. I had already pondered, “What if … No problem, we can always…” I paused the meeting, acknowledged that our stated objectives were challenging and identified a new goal for the group. From thinking in advance about how the meeting could wrong, I was able to make concessions in the moment and still persist with getting most of the work done.

To close I return to Holiday’s final thoughts,

See things for what they are.

Do what we can.

Endure and bear what we must.

What blocks the path now is a path.

What once impeded action advances action.

The Obstacle is the Way.

None of this is simple and it takes practice. I know that I am a better coach and facilitator from practicing the Stoic maxims discussed in the Holiday’s work.

What internal dialogue might you offer yourself in order to build your capacity when you encounter obstacles?

How might you be a model to others in the Discipline of the Will?

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