Letters to Malcolm & The Problems of Prayer

The Grace of Common Prayer #1

This is the first in a five part series on prayer. You can find all the posts at the following links: Part I, Part II, Part III, Part IV, Part V

INTRODUCTION

When C.S. Lewis penned a series of letters in 1953 expressing his desire to write a book on prayer, he identified a challenge that remains pressing today. Writing to Fr. Giovanni Calabria, he explained: "I am trying to write a book about private prayers for the use of the laity, especially for those who have been recently converted to the Christian Faith."¹ Lewis was particularly troubled by the tension between Jesus' submissive prayer in Gethsemane ("not as I will, but as you will") and His bold promise in Mark 11:24 ("whatever you ask in prayer, believe that you have received it, and it will be yours"). "Both statements are the Lord's," Lewis noted, "both are among what we are required to believe."² How can both be true?

This tension between submission to God’s will and boldness in asking God to grant our requests in prayer, along with other theological puzzles, so vexed Lewis that by 1954 he abandoned his intended book on prayer. Instead, he turned to fiction, writing the beloved Chronicles of Narnia as a way to approach complex spiritual truths through imagination. While this shift to children's literature proved a blessing to Christians everywhere—the Narnia books have shaped countless theological imaginations, including my own—the questions that troubled Lewis about prayer remain largely unanswered for many believers today.

THE PERSISTENCE OF PRAYER'S PROBLEMS

My experience teaching a theology of prayer course to undergraduates from 2006 to 2022 reveals how enduring these challenges are. Most of my students came from large, non-liturgical evangelical churches and approached prayer with sincere enthusiasm. Yet when prompted to reflect on their prayer lives, they expressed struggles remarkably similar to those that troubled Lewis. Consider these recurring themes from student reflections:

“Sometimes when I pray, I feel like my words are just bouncing off the ceiling. It's like God isn't even listening."

"There are times when I sit down to pray, and it's just... nothing. I’m emotionally drained and have no feeling, no connection. It's like talking to a blank wall. I wonder if God has gone silent, or if I've somehow lost my way."

"If God already knows everything we need, why do we have to ask Him for anything? Isn't prayer redundant?"

"Every time I try to pray, my mind starts wandering. I end up thinking about my grocery list or work deadlines instead of focusing on God."

"Can our prayers actually change God's mind? If He's all-knowing and perfect, why would He alter His plans based on our requests?"

"Sometimes I wonder if I'm even worthy enough to pray. What if I'm not doing it right or I'm not holy enough for God to listen to me?"

"I feel guilty when I don't pray at certain times or in certain ways. It's like there's this unspoken pressure to pray 'correctly'."

"When something good happens after I pray for it, I'm never sure if it's really an answer to prayer or just a coincidence. How can I tell the difference?"

"I hate to admit it, but there are days when I wonder if prayer really changes anything. We pray for healing, for peace, for change – and sometimes it seems like nothing happens. It's hard not to question."

"I start every week with good intentions for daily prayer, but by Wednesday, my schedule is in chaos. It's frustrating how quickly my spiritual disciplines can unravel."

These testimonies reveal something crucial: while the specific language may have changed, the fundamental struggles with prayer that Lewis sought to address remain powerfully present in contemporary Christian experience. This continuity is no accident. While Lewis wrote in mid-20th century Britain and my students speak from early 21st century America, both contexts share a crucial feature: the rising tide of what philosophers now call "expressive individualism." Lewis witnessed its early manifestations in post-war Britain, as traditional religious frameworks began giving way to more individualistic approaches to spirituality. My students inhabit a world where this shift has reached its full expression. That Lewis so precisely anticipates their struggles suggests he recognized this cultural trajectory and its implications for prayer.

ON PRAYER’S “IRKSOMENESS”

It's important to clarify what I'm suggesting about prayer in this series. I am not claiming that prayer offers no struggle—indeed, the entire Christian tradition attests to prayer's genuine difficulty. What I am suggesting is that this difficulty itself has theological significance. The struggle we experience in prayer is not evidence that prayer is fundamentally our achievement, but rather testimony to our fallen condition being gradually restored through grace.

Prayer is a "graced struggle"—difficult precisely because it involves the restoration of something essential to our nature that has been damaged. C.S. Lewis candidly acknowledges in his Letters to Malcolm that "prayer is irksome. An excuse to omit it is never unwelcome.…” (Letters to Malcolm, Letter 21). Importantly, this struggle doesn't contradict prayer's character as divine gift but reveals the disparity between what we are and what we are meant to be. Any progress we make in prayer must be credited ultimately to the sovereign work of God, though it certainly involves our active—but graced—participation. As Augustine might say, God gives what He commands when He commands us to pray (see Confessions 10.29.40). As I’ll make clear as this series continues - God does indeed promise and give what he commands. He gives us the Word - eternal, incarnate, and written - which becomes our prayerful response to His summons.

THE CONTEMPORARY RELEVANCE OF LETTERS TO MALCOLM

Though Lewis never completed his intended book on prayer, his posthumously published Letters to Malcolm: Chiefly on Prayer³ engages deeply with these persistent challenges. The questions Lewis explores in his fictional dialogue with Malcolm mirror with remarkable precision the concerns my students—and I suspect many others—continue to wrestle with today.

For example, when students worry about their prayers "bouncing off the ceiling" or God's apparent silence, they echo questions that Lewis wrestles with extensively in Letters 4, 8, and 9, where he explores the nature of divine responsiveness. Similarly, their doubts about whether they're "just talking to themselves" are addressed in Letters 13 and 15, where Lewis probes the nature of prayer as genuine dialogue, most memorably through his analysis of a poem about divine-human communication. The emotional and practical challenges of prayer also find thorough treatment in Lewis's letters. Students' feelings of being "emotionally drained" or disconnected mirror Lewis's careful examination of the relationship between feelings and authentic prayer (Letters 15, 21).

Their struggles with wandering minds and maintaining prayer disciplines are acknowledged in Letter 21, where Lewis speaks candidly about prayer's "irksomeness." Questions about praying "correctly" or being "worthy enough" find thoughtful response in Letters 2 and 3, where Lewis discusses the merits of both formal and spontaneous prayer. The deeper theological puzzles that trouble students are precisely those that Lewis grapples with most profoundly. When students ask whether prayer can "change God's mind," they raise the same question Lewis explores in Letters 9 and 10 regarding divine immutability and prayer's efficacy. Their questions about why we should petition a God who already knows our needs receive careful attention in Letters 4 and 5.

Finally, their difficulty distinguishing "coincidence" from answered prayer leads to the same territory Lewis explores in Letters 7 and 8, where he examines how divine action interfaces with natural events. This profound resonance between contemporary struggles and Lewis's analysis reveals something crucial: the challenges of prayer cannot be addressed merely through better techniques or stronger discipline. As Lewis demonstrates throughout Letters to Malcolm, authentic prayer emerges not from our own capabilities but from our participation in the divine life through Christ. Prayer is fundamentally a gift of grace—from beginning to end—with even our struggles and imperfections encompassed within God's redemptive work. (See Romans 8:26-27).

Apart from the gospel of grace, Christian prayer is like an inside joke whispered in a foreign language - doubly incomprehensible to those standing on the outside. It's like trying to join a symphony orchestra without knowing how to read music or play an instrument. It's like stepping into the final act of a grand drama without knowing the characters or their story. Like attempting to understand the joy of a family reunion when you don't know any of the shared histories, private nicknames, or unspoken traditions that bind them together. Each attempt at prayer, without the context of grace, becomes like trying to unlock a door with a key you haven't been given.

Prayer – to be much more direct - is a fundamental part of our redemption in Jesus Christ and must be understood as such. The Christian’s progress in prayer is a restoration of the communicative dimension of our communion with God.

THE CHALLENGE OF EXPRESSIVE INDIVIDUALISM

The resonance between Lewis's concerns and contemporary struggles with prayer points to a deeper cultural shift that both Lewis and we inhabit. Our difficulty with prayer isn't merely a matter of discipline or technique—it reflects fundamental assumptions about the relationship between the self, God, and reality itself.

Looking again at the student testimonies cited above, we can distinguish between practical concerns ("my mind wanders," "my schedule is in chaos," "I'm emotionally drained") and theological questions ("can our prayers change God's mind?" "am I worthy?" "does prayer change anything at all?"). Yet underlying both types of concerns is a common presumption: prayer originates with us and is directed toward a passive, receiving God. Success in prayer, by this understanding, depends on our initiative, our concentration, our worthiness, our ability to influence divine action.

This assumption—that we are the primary actors in prayer—reflects what Charles Taylor, Carl Trueman, and others identify as "expressive individualism," a dominant cultural paradigm of our age. This framework places individual authenticity and self-expression at the center of human meaning and fulfillment. While Lewis didn't use this terminology, he recognized and critiqued this shift in his cultural moment, seeing how it would increasingly shape (and distort) Christian spirituality. Importantly, The Abolition of Man⁴ is widely considered Lewis’s most important philosophical work, and that seminal text is among the 20^th century’s foundational works to identity the cultural trends now identified as expressive individualism.

In The Abolition of Man, Lewis warned of a profound cultural shift taking place in the West - the rejection of what he calls "the doctrine of objective value." This rejection, Lewis argues, has devastating consequences. When a civilization abandons the belief that there are objective standards of truth, beauty, and goodness to which all people must conform, it leaves its members with nothing but their own subjective impulses as guides. As Lewis puts it in chapter one, "The right defence against false sentiments is to inculcate just sentiments. By starving the sensibility of our pupils we only make them easier prey to the propagandist when he comes. For famished nature will be avenged and a hard heart is no infallible protection against a soft head."

This is precisely what scholars like Charles Taylor and Carl Trueman now identify as the "poietic" approach to truth and meaning - where truth and meaning are thought to arise from within the individual rather than being discovered in an objective order that exists beyond ourselves. Lewis saw this coming, recognizing that once a civilization rejects objective value, it inevitably produces what he called "men without chests" - individuals who can neither recognize nor respond appropriately to transcendent truth because they have been taught to look only within themselves for meaning. In their world, all truth claims become mere expressions of personal preference rather than participation in an objective reality that makes claims upon us.

This shift from objective value to subjective preference that Lewis identified has profoundly shaped how modern Christians approach prayer. Rather than seeing prayer as participation in an objective reality - the eternal communion of the Trinity - many now approach it primarily as a form of spiritual self-expression. The question becomes not "How do I conform myself to the reality of God?" but rather "How do I authentically express my spiritual self and perhaps bend God to my own will?" Prayer becomes less about receiving and responding to divine grace and more about articulating our own thoughts, feelings, and desires in the hopes that God will be moved.

The influence of expressive individualism represents a profound shift from an ancient mimetic to a modern poietic approach to prayer and spiritual life:

This shift helps explain why traditional Christian prayer practices often feel foreign or burdensome to modern believers. When prayer is understood primarily as self-expression—as originating from within us and dependent on our effort—it becomes another task we must perfect, another responsibility we must bear. Lewis recognized this burden and consistently pointed toward an alternative vision: prayer as grace from beginning to end – a graced participation in the Word of God.

THE GRACE OF COMMON PRAYER: A WAY FORWARD

The burden of prayer we've discussed stems not from prayer itself but from our misunderstanding of its nature. Consider these transformative questions, which I’ll address in the next few posts:

1. What if prayer were not a burden, but a gift - pure grace from start to finish?

2. What if the content of our prayers originated not from within us, but from God Himself?

3. What if both the initiative and the ultimate efficacy of prayer were God's responsibility and not ours?

These questions point us toward what I believe is the heart of authentic Christian prayer – it is grace from beginning to end. In the next few posts, I'll explore Christian prayer from several vantage points, showing that it is wrongly conceived as a human achievement and rightly understood as participation (koinonia) in the eternal communion of the Trinity. This understanding, embodied particularly well in the Anglican Prayer Book tradition, offers a way beyond the individualizing tendencies of our age into the freedom of a grace-shaped relationship with God.

1. Lewis, Calabria, and Moynihan, Letters.

2. Lewis, Calabria, and Moynihan, 79.

3. Lewis, Letters to Malcolm, Chiefly on Prayer.

4. C.S. Lewis, The Abolition of Man.