A Reader’s Guide to a Christian Classic

Tim Keller didn’t write a book on prayer because he felt like an expert. By his own admission, he embarked on his yearslong study out of a sense of deficiency and necessity. He opens the first chapter by saying,

In the second half of my adult life, I discovered prayer. . . . It became clear to me that I was barely scratching the surface of what the Bible commanded and promised regarding prayer. (9)

When I first read those lines as a recent seminary graduate, I could hardly believe them. Tim Keller, a spiritual giant, preaching to thousands, publishing books, and yet barely scratching the surface?

He ties his prayer-life-changing discovery to his diagnosis of thyroid cancer in 2002. When the news came, he was in his early fifties and nearly thirty years into pastoral ministry. He had been pastoring Redeemer Presbyterian Church in New York City for more than a decade. And then cancer did what adversity often does: it sparked something of a revival in his heart, an awakened sense of both his spiritual neediness and the powerful privilege we enjoy on our knees.

His prayer crisis sent him on a quest deep below the surface to experience the awe and intimacy that God promises to those who pray. Twelve years later, he sketched out a map, in fifteen chapters, of all he’d tasted and seen for those who want to go deeper themselves.

Emboldening Humility

Part of the power of the book is in its endearing humility. At one level, it really is an extended confession of how (unconsciously) inadequate his prayer life had once been. In an interview after the book released, he shared,

My wife and I would never want to go back to the kind of prayer life or spiritual life we had before the cancer. I really thought that I had a good prayer life. And when I broke through into another dimension, I realized that, frankly, my prayer life wasn’t very good.

His own personal humbling, and the subsequent years of concerted effort to grow, make the book both convicting and emboldening. Convicting, because we may find ourselves receiving the same diagnosis he received: frankly, our prayer lives aren’t very good. Emboldening, though, because he makes a vibrant prayer life feel wonderfully possible again. He’s relentlessly realistic about the difficulties of genuine prayer, but he also models grace-filled, joy-hungry perseverance in prayer.

“I can think of nothing great that is also easy,” he writes. “Prayer must be, then, one of the hardest things in the world” (24). He’s after a deeper experience in prayer that he himself had neglected and forfeited over many years. In the first pages, he tells us what he wants the reader to feel when we pray:

This book will show that prayer is both conversation and encounter with God. . . . We must know the awe of praising his glory, the intimacy of finding his grace, and the struggle of asking his help, all of which can lead us to know the spiritual reality of his presence. Prayer, then, is both awe and intimacy, struggle and reality. (5)

This quest sent him deep into church history, where he knelt beside spiritual forefathers like Augustine, Luther, and Calvin (along with Owen, Edwards, Lewis, Lloyd-Jones, Packer, and more). He uncovers a letter Augustine wrote to a woman who feared she was failing in prayer. He comes alongside Luther as he counsels a barber broken by sin and tragedy. He sits in on Calvin’s “master class” on his five rules for prayer. He listens to the similar and distinct ways all three pastors prayed the Lord’s Prayer. All of this makes the book a treasury of help from ancient prayer closets.

Praying Well Begins with Listening

For Keller, perhaps the single most important key to prayer is its marriage to the word of God. So many of the dangers of prayer are curbed (or eliminated altogether), and so many of the rewards are unlocked and unleashed, when we pray over and through and from what God has said.

Your prayer must be firmly connected to and grounded in your reading of the Word. This wedding of Bible and prayer anchors your life down in the real God. (56)

Without immersion in God’s words, our prayers may not be merely limited and shallow but also untethered from reality. (62)

Keller doesn’t set the Bible aside to try and have a better prayer life, as if an overemphasis on Scripture somehow undermines our prayers. No, the greater danger is that we can actually lose the true God in our rhythms of prayer. “If left to themselves our hearts will tend to create a God who doesn’t exist,” he warns. “Without prayer that answers the God of the Bible, we will only be talking to ourselves” (62).

After establishing the importance of Scripture early in the book, he circles back and does a whole chapter on how the practice of meditation serves prayer, letting John Owen teach us how to work the truth out with our minds and then work it in to our hearts.

Prayer Closets for Beginners

Keller was a theologian and an apologist, but he was just as much a pastor. And because he was a pastor of people who really struggled to pray, he wasn’t content to merely share ideas and principles. He wanted to offer real practical help on the how.

I wrote this book because, though many great books on prayer have been written, most either go into the theology of prayer, or they go into the practice of prayer, or they troubleshoot. I didn’t have one book I could give people that basically covered all the bases: a biblical view of prayer, the theology of prayer, and some methods of prayer. I didn’t have a good first book to give somebody. (“Prayers That Don’t Work”)

So, after developing a theology of prayer in Scripture and exploring what history teaches us about prayer, he offers ways to actually practice and experience what he’s describing.

For instance, he devotes a chapter to praying the Lord’s Prayer (Matthew 6:9–13). That may sound rather straightforward and elementary at first (you may have started praying that prayer even before you were in first grade), but Keller follows Luther in learning to use the prayer less for its exact words and more as a pattern to follow and expand in our own words (93–94). He found that this practice limits the distracting thoughts that inevitably come when we pray. It also teaches us to reach beyond the immediate needs or burdens that so often dictate where we focus in prayer.

Later in the book, he shares how regularly praying the Psalms transforms a prayer life.

Immersing ourselves in the Psalms and turning them into prayers teaches our hearts the “grammar” of prayer and gives us the most formative instruction in how to pray in accord with God’s character and will. (255)

He shares that he would read psalms in the morning and evening and then pray, sometimes praying the actual words of the psalm and other times praying in his own words. Following the The Book of Common Prayer schedule, he would work through all 150 psalms each month. Over time, his prayers (and soul) were slowly and deeply conformed to “the Bible’s prayer book.”

Along with the Lord’s Prayer and the Psalms, he collects and shares a number of other extremely practical paradigms and guides for daily prayer, ranging from short and simple models to longer and more involved ones.

Entering the Happiness of God

Having read a number of Keller’s books, perhaps the most surprising character in this particular book was joy. In fact, rereading the book made me wonder if his battle with cancer freshly awakened him not only to prayer, but also to the prominent place of happiness in the Christian life. Very early, he charts the course:

The Westminster Shorter Catechism tells us that our purpose is to “glorify God and enjoy him forever.” In this famous sentence we see reflected both kingdom-prayer and communion-prayer. Those two things — glorifying God and enjoying God — do not always coincide in this life, but in the end they must be the same thing. We may pray for the coming of God’s kingdom, but if we don’t enjoy God supremely with all our being, we are not truly honoring him as Lord. (4)

For as sweet as the camaraderie was between Tim Keller and John Piper over the years, I don’t think I’ve ever heard them sing with such harmony. According to Keller, the prayers “Hallowed be your name” and “O God, my soul thirsts for you” are not unrelated or at odds, but at their deepest root, the same.

And why would our enjoying God glorify him? Because he is Happiness — Father, Son, and Spirit infinitely and eternally delighting in one another. “We can see why a triune God would call us to converse with him, to know and relate to him. It is because he wants to share the joy he has. Prayer is our way of entering into the happiness of God himself” (68). From his knees, Keller found the only thing big enough, full enough, and intense enough to satisfy the human soul: joy in the happy God.

And now that joy is full. On May 19, 2023, Tim Keller went from prayer to sight. In the sovereign hands of a loving Father, cancer had given him prayer, and now cancer has given him Christ. He has truly entered the happiness of God. Oh, to read a sixteenth chapter from heaven.