St. Theresa of Avila once offered some great advice on prayer: “Pray as you can, not as you can't.” Prayer, first of all, is a conversation with a loving God. Conversation means you can and should talk to God about anything and everything.
The question about discipline in prayer, however, is a good one. We can look at discipline in two ways. Discipline can drain us of life or discipline can keep us focused.
Sometimes people ask if they aren't praying well when they are no longer attracted to praying the rosary as they once had been. In this case, a "discipline" that forced one to pray in ways that no longer give life would not be helpful. This person needs to be more attentive to how God is calling them to pray at this stage of their life.
Another case entirely is a person who reads book after book, dabbles in this type of prayer or that, consults this person or someone else, and in the end discovers that they have gotten nowhere in prayer. This person resembles a hiker who follows many different paths for only a few feet before turning back and taking another. They never really go hiking or get to see the wonderful forest or mountains they initially came to hike. This person does need discipline, that is, they need to be more intentional about listening to where God is calling them and sticking with it.
In both cases, attentiveness to God is the key, being attuned to how he is working in one's life. The issue is not necessarily one of discipline, but one of obedience and focus.
The following resources might be helpful in discovering where God is calling you on the path to prayer. These might help you try different "styles" of prayer until you notice an "affinity" with one or other of them. Then stick with it for a period of time. After a while you may notice that God is shifting his way of being with you. You can shift your way of praying accordingly. It is normal throughout our life that different forms of prayer will help us draw closer to our God at different points in our life’s journey. There is a continuum of spiritual development, an arc or horizon of the spirit, and as we grow and change and mature different forms of prayer become more important to us.
Beginning Contemplative Prayer: Out of Chaos Into Quiet. By Kathryn J. Hermes, FSP. This is a practical guide to contemplation that helps you "try on" various prayer methods. Sometimes our prayer seems to have “dried up” simply because we are still praying according to what we learned as children. During our life we relate to people in different ways. The same happens in our relationship with God. In fact there is an arc of spiritual growth that saints have mapped out for us. This book helps you grow in prayer so that you satisfy the longing in your heart for "more."
Peace in Prayer: Wisdom from Teresa of Avila. This is a great book if prayer seems boring or you find yourself distracted when you try to pray. It answers the question: I love God, but my prayer doesn't seem to be going anywhere. Why? In this book you get solid advice from a saint!
Path of Holiness: Wisdom from Catherine of Siena. Another saint with advice for the person serious about their relationship with God and their prayer…. Catherine of Siena was a mystic, yet very down to earth, as she guided the priests, religious, and lay people who followed her.
A Simple Life: Wisdom from Jane Frances de Chantal. This simple method of prayer can help you find peace when life seems to be pulling you in a thousands different directions. St. Jane Frances' advice given both to her sisters in the Visitation Congregation she founded with St. Frances de Sales as well as to the lay people who wrote to her for counsel is both gentle and strong. She will help you develop a form of prayer that can unify your life.
Christ in Our Midst: Wisdom from Caryll Houselander. Prayer isn't something that happens only in moments of quiet or in a church. Prayer makes one ready to find Christ everywhere and provides the strength to have faith in Christ's presence also in the places and people obscured by sin, stress, and difficulty. Caryll Houselander, an unconventional mystic, opens up a way to seek the face of God in daily life and to discover Jesus in every person we meet.
Sr. Kathryn J. Hermes, fsp