‘Cultivating Discipline Lightly’ is a weeklong course running during the second week of September 2013 at Kaos Pilots in Aarhus, Denmark. This course offering grew out of the need for Kaos Pilots students, who will be on their own during their final year as they work on their social business project, to learn how to respond well in the face of great uncertainty. Last year, Pete Sims asked me to come in and put on a workshop on the art of philosophical inquiry entitled ‘Confusion and Clarity: The Art of Inquiry in the Context of Social Enterprise.’ Learning to inquire proved helpful and necessary but not sufficient. What was wanting still was the cultivation of a kind of discipline–one requiring good guidance, one invoking the right set of virtues, yet one also honoring the lightness and humor of things–that would see them through the unsettledness. Hence this course: cultivating discipline lightly.

What follows is a layout of the guide I’m writing for Kaos Pilots students. Enjoy.

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Rip Van Winkle: A Parable

Story: Rip Van Winkle falls asleep in one world and wakes up in another. What now? What does this mean for us?

Chapter 1. Raising and Lowering Our Eyes

Argument: I discuss the concept of authority, the structure of authority, types of authority, and–most importantly–our present need for legitimate authority.

Chapter 2. Acknowledging Our Unsettled Time

Argument: I ground my account of unsettled time on three related theses:

i. All claims to legitimate authority appear suspect in our eyes and have failed to gain our approval. ‘Who is to lead whom and by what right?’ seems impossible to answer wholeheartedly. (Halfhearted answers there are aplenty.)

ii. Skepticism has saturated our daily lives to such an extent that our words have become seeded with doubt and our attitude toward others has become starched and blanched with distrust, uncertainty, and reticence.

iii. Despite the crisis of authority and the near universality of our skepticism, we as socially dependent beings who need to act in concert with one another, to figure out what is unknown about ourselves, and to find a way to reach mutual understanding.

Chapter 3. Building a Sturdy Trellis

Argument: I draw from the work of St. Benedict to provide a beautiful vision of a different kind of organizational life. A trellis is the metaphor for the framework upon which an individual can grow by means of philosophical friends and a philosophical guide. A trellis, accordingly, is an answer to the question of good authority.

Chapter 4. Learning to Inquire

Argument:  How does one grow in and through good guidance? Inquiring, I argue, is the kind of activity that takes place between guide and conversation partner. Specifically, philosophical inquiry is an ‘unrehearsed genre whose chief aims are to reveal to us what we do not know but thought we did and to bring us a greater sense of clarity than we could have possibly imagined’ (definition from The Art of Inquiry). It is rather like saying, ‘I don’t know. Let’s find out.’ Inquiring begins in some state of confusion (bewilderment, puzzlement, or bafflement); proceeds in a state of mind that is wholly dispassionate; requires the virtues of courage, patience, openness, and humility; and ends in a state of clarity (illumination, laughter, lightness).

Chapter 5. Becoming Lighthearted

Argument: The best form of education is one that cultivates one’s character. My philosophical guide Pierre Hadot suggests that character is cultivated by means of ongoing spiritual exercises (ascesis). What sorts of exercises, apart from and together with inquiring, will allow one to become lighthearted in the face of unsettledness?  In this chapter, I explore a handful of spiritual exercises whose purpose is to bring about the kind of character that is properly, energetically, and lightly responsive to ordinary surprises. It’s only an apparent paradox to say that inquiring teaches us to be prepared for responding well–lightheartedly rather than stoically or resiliently–to we know not what.

Appendix: Getting the Hang of Being Surprised

Argument: In Part 1, I discuss the importance of being surprised, arguing that philosophical inquiring presents us with two kinds of surprises: perplexities and illuminations. In Part 2, I discuss the cultivation of lightness in the presence of surprise. In the final part, I explore the difference between other states of mind and an inquiring state of mind.