I’ve read quite a few books on the subject and wanted to point to 5 that I’ve found particularly helpful. Here they are, in no particular order.

Praying Backwards by Bryan Chapell. Where this book helped me most was in leading me to pray with an increased reliance on the work of the Holy Spirit. Here’s how I phrased it in my review: “This book was such a joy to me. It removed a burden I have so often felt in prayer, that I need to say, feel or know just the right things in order to make my prayer effective. But I had never fully understood the Spirit’s role in prayer, that He intercedes in every prayer, taking my limited, far-too-human perspective, and presenting to the Father a prayer that is beyond time and space – a prayer that is formed through the Spirit’s omniscience. No wonder, then, that God can and will answer prayer! I know now that my role is not to feel the need to pray great prayers, but it is to continue to grow in godliness – for even the simplest prayers can be pure and sweet to the Father – that I may more and more resemble the Son to whom I am united.”

A Praying Life by Paul Miller. One of the areas in which this book spoke to me was in the way it moved me away from structure, at least in certain cases. We’ve all been taught ACTS or another model for prayer. These are often very helpful guidelines for praying carefully and systematically. But where Miller helped was in freeing me from those under certain circumstances so I could pray “randomly,” praying as my mind moved from one thing to the next. There is a certain freedom I’ve found in that, realizing that structure is not the same as depth. In my I point to another strength. “Perhaps the greatest strength of this book is Miller’s unrelenting emphasis that prayer cannot be an add-on to the Christian life; it cannot be supplemental but must always be instrumental. This book will equip you to understand prayer properly and, on that firm foundation, to commit yourself to it, with confidence that God is willing and able to hear and answer your prayers.” 

The Prayer of the Lord by R.C. Sproul. In this book R.C. Sproul teaches on prayer by drawing principles from the Lord’s Prayer. I don’t know that I can easily quantify the ways in which this book impacted me, and yet I know it did. What I did draw from it was a long list of excellent quotes on prayer–the kinds of quotes you want to write out and chew on for a while. “Prayer does change things, all kinds of things. But the most important thing it changes is us. As we engage in this communion with God more deeply and come to know the One with whom we are speaking more intimately, that growing knowledge of God reveals to us all the more brilliantly who we are and our need to change in conformity to Him. Prayer changes us profoundly.” Or this one: “I find it striking that when Jesus taught the church how to pray, the first thing He chose to tell us to pray about is that the name of God might be regarded as sacred. Very few people today would list the hallowing of the name of God as a top priority for the supplications of the people of God. It almost seems foreign to our environment to place so much emphasis on proper treatment of a name.”

The Valley of Vision. You’ll have to allow me to explain this one. It’s all trendy today to read and proclaim your love for The Valley of Vision. I can’t say that it’s ever quite impacted me as much as it has others. But prayers like this one–old prayers written out and handed down–have impacted me quite a bit. It is one thing to learn to pray from reading about prayer; it’s quite another thing to learn to pray by reading actual prayers. And that’s where I’ve found The Valley of Vision and other collections of printed prayers so valuable.

A final word on prayer: In the end the way you’ll best learn to pray is by praying. We can read about it all day long, but at the end of it all, you’ll just need to close your eyes and pray. There are no experts in prayer; we are all learning, all growing, all reaching for the Lord. But maybe one or two of these books can give you just a little nudge in the right direction.