Playing Devil’s Advocate: Vocational Wisdom from The Screwtape Letters

In a previous post, I wrote about assigning “Learning in Wartime” in a vocation seminar when COVID first hit. I wrote about how profound that text was for my students and about their moving responses to Lewis’ sermon. Here, I want to describe the next reading I assigned, The Screwtape Letters, which was equally engaging to students, similarly insightful about vocation, and provided them with an essential skill for persisting in the right direction: playing devil’s advocate.

If “Learning in Wartime” presents Lewis as a kind of good angel on student’s shoulders encouraging them to pursue their vocations in the face of fear, anxiety, cultural upheaval, and looming death, then The Screwtape Letters present the dark angel, the voice of a demon, of our inner demons. The book plays devil’s advocate to faith, hope, love, virtue, goodness, clear thinking, inner peace, and healthy relationships. It does this by inverting the Christian worldview. God is “the Enemy.” Satan is “Our Father Below,” and Screwtape and Wormwood are inversions of guardian angels. The letters embody Satan’s line from Paradise Lost: “evil be thou my good.”  Like the genre of literary tragedy that cautions us by showing how the aspirations of noble characters end in calamity, reading The Screwtape Letters can help us preempt our demons, whether inner demons or external ones; it can help us see our blind spots and remind us that good things can be traps and seemingly bad things can contain blessings. I’ve found that having students write their own Screwtape letters offers them an eye-opening way of looking at the circumstances of their own lives. Playing devil’s advocate to one’s own vocation is a generative exercise.

As the pandemic took over our lives, I couldn’t help but think of my students (and myself) when I came across the following passage. In it, Screwtape discusses how to handle the thoughts of the unnamed young man, about college-aged, who is the focus of Screwtape’s letters and who Wormwood has been assigned to tempt and destroy. The young man is old enough for military service but not sure if he’ll be called up for it:

We want him to be in maximum uncertainty, so that his mind will be filled with contradictory pictures of the future, every one of which arouses hope and fear. There is nothing like suspense and anxiety for barricading a human’s mind against the Enemy. He wants men to be concerned with what they do; our business is to keep them thinking about what will happen to them . . . It is your business to see that the patient never thinks of the present fear as his appointed cross, but only of the things he is afraid of . . . let him forget that, since they are incompatible, they cannot all happen to him, and let him try to practice fortitude and patience to them all in advance. For real resignation, to a dozen different hypothetical fates, is almost impossible, and the Enemy does not greatly assist those who are trying to attain it; resignation to present and actual suffering, even when that suffering consists of fear, is easier and is usually helped by this direct action . . . Tortured fear and stupid confidence are both desirable states of mind.

C.S. Lewis, The Screwtape Letters

This and all the other experiences the young man goes through—falling in love, making good and bad friends, wrestling with his faith, bickering with his mother, all of which are overshadowed by the war—resonated deeply with my students. The book combined a fresh way of looking at ordinary experiences with a sobering reminder that vocation is always in peril.

Screwtape’s main goal, his “real business,” is “undermining faith and preventing the formation of virtues.” This is worth pondering in vocational terms. What does one need faith in to have and sustain a calling? A caller? A sense that purpose and meaning are not merely self-constructs? That, talent-wise, you have what it takes to make it in your chosen field? That staying in a rough marriage or friendship is worth it? That it’s wise to leave a job that has one headed for—or already in—vocational hell? What, for each of us, most consistently prevents the formation of virtues?  What would Screwtape advise Wormwood to do about us?

One point, among many, that Lewis makes regarding the formation of virtues and habits is especially interesting in regards to vocation. This is the “disappointment or anticlimax . . . [that occurs] on the threshold of every human endeavor . . . In every department of life it marks the transition from dreaming aspiration to laborious doing.” When students, who have dreamed of becoming doctors and writers and CEOs arrive at college, those dreams can seem to vanish in the grind of heavy course loads. It’s good for them to understand this is normal. It will happen when they graduate, get the jobs that they’ve dreamed of, and buckle down to the real work of those jobs. This is normal, and it is also the path to developing persistence, grit, and character. Of course, if their courses or jobs are only grind and misery, that might be a sign that they should rethink their choices.

Most everything else in the letters is aimed at undermining faith and preventing the formation of virtue. Screwtape’s first line of assault is on our thinking: he wants a distracted, muddled, unquestioning mind: “as in everything else, the way must be prepared for your moral assault by darkening his intellect.” “It is funny,” Screwtape later muses, “how mortals always picture us putting things into our minds; in reality our best work is done by keeping things out.” And later, most chillingly, he advises Wormwood, “Keep everything hazy in his mind now, and you will have all eternity wherein to amuse yourself by producing in him the peculiar kind of clarity which hell affords.” A hazy, fuddled mind makes Screwtape’s job easier, and it sets us up for the foolishness, temptations, and discouragements that prevent the formation of virtue.      

So many of the Letters are student favorites: The first Letter about clear thinking. Letter four on prayer. Letters eight and nine on what Screwtape calls “the law of undulation” (that the only constant to human life is being always up and down). Letter fourteen on humility, and letter twenty-nine on courage.

But the final letter is perhaps the most challenging and compelling to students. In the final letter, the young man is killed instantly by a bomb in what appears to have been an air raid. This letter presents the ultimate example of something that from our view looks terrible (and is terrible), but that turns out to be, from an eternal perspective, evil turned to good. Screwtape remarks of the young man’s death:

He got through so easily! No gradual misgivings, no doctor’s sentence, no nursing home, no operating theatre, no false hopes of life; sheer, instantaneous liberation. One moment it seemed to be all our world; the scream of bombs, the fall of houses, the stink and taste of high explosives on the lips and in the lungs . . . the heart cold with horrors, the brain reeling, the legs aching; the next moment all this was gone, gone like a bad dream, never again to be of any account.

C.S. Lewis, The Screwtape Letters

This is not meant to minimize the senseless brutality of a young life cut short. This last letter is a provocative call of hope; it is the challenge to believe, despite what we see clearly before us, that the worst tragedy can still turn out to be the greatest comedy.

In letter nineteen, Screwtape claims that the one thing that hell has not yet understood is love. He believes there must be some real motive behind God’s “cock and bull story about disinterested love.” And that’s the secret. The Screwtape Letters show us a world where love does not exist. The letters teach us to ponder the choices and habits that would form the path of anti-vocation.   


Jason Stevens is an Associate Professor of English at Cornerstone University in Grand Rapids, MI. He is interested in the role of the imagination, particularly the poetic imagination, in places of political violence and distressed social conditions, and is currently at work on a book about Seamus Heaney, poetry, and purpose. Click here to see other posts by Jason at Vocation Matters.

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