Wicked Questions & Discernment

What is a wicked question?

Description automatically generated Wicked questions are often defined by their unpleasant, unpredictable or unreasonable nature. They are, in short, the questions most worth asking.

According to Marshall Watson of Louder Than Ten, a project management group that promotes critical reflection and inquiry: "Modern western society places far more value on answers than it does on questions... Good questions are often powerful and inspiring. But really important questions can also be scary or difficult to ask (and even scarier and more difficult to answer). Our truly wicked questions can feel unpleasant and unreasonable while also feeling exceptional and important; they embody a tension between good and bad, scary and inspiring."

In my capacity as a spiritual companion, I find that these kinds of uncomfortable (wicked) questions often assert themselves in the private, reflective moments of spiritual direction. Queries that arise are more and more frequently those that surround one's religious affiliation or spiritual practice and whether or not that affiliation/practice currently supports, nurtures, challenges, and compels one to deeper encounters with Holy Mystery.

In his latest book, Do I Stay Christian?, A Guide for the Doubters, the Disappointed, and the Disillusioned, author, activist, public theologian, and international speaker, Brian D. McLaren, explores such questions from his own personal experience of struggle with and discernment of these wicked questions. The book is divided into three sections: 1) LEAVE; 2) STAY; 3) HOW TO MOVE FORWARD.

With candor, sensitivity, and a spacious neutrality, McLaren presents the ways in which historical facts, spiritual insights, and stories from his own encounters with others, have challenged his own awareness and perspective.

Margie Will, Sister of St. Francis
Executive Director, Franciscan Living
Profile: http://stfrancisprovince.org/margie-will