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Into Prayer: When? Where? How? (Prayer IV)

Transformation Blog: Readings from Learning to Live and Love Like Jesus



Into Prayer: When? Where? How? (Prayer IV)

Brandon Cook

So, how do we set our hearts to prayer, that we may learn to “always pray?” We learn to always be in prayer by setting aside time dedicated only to prayer. We’ve covered the “what” and the “why” above, but what about the “when,” “where,” and “how”?


Whenever works! Many will tell you—and Christian tradition seems to uphold the idea—that morning is the time to pray, before your mind is crowded with thoughts. Yet Jesus is often recorded praying at night, sometimes in the deep night. Some people say we should pray in the morning, then at noonday, then at evening, then at bedtime. Some say taking a couple of long prayer “baths” each week is better than taking a daily “shower.”

Clearly then, there’s no one way to pray. What’s moreimportant isthat we have some consistency, fueled by our longing—and even better, our love—for God, and our desperate need to be aware of His nearness and goodness, no matter the storm or calm. I’m sure Jesus prayed with intentionality daily, though it appears he also set longer, dedicated times of prayer throughout his week and month. The main thing that influences the “when” is personality and temperament. We need to discern how we, as individuals, best posture our hearts to pray and hear. At the same time, we may need to discipline and train our personality and temperament.  

What’s clear for all of us is that it will take work. Practicing prayer means creating free, unhurried space. There’s a reason we order our spiritual practices starting with The Slow Life. Unhurriedness, silence, Sabbath, and hospitality are boulders that create space for the power of grace to fill our lives, but they also create space for more practices, like Scripture-reading and prayer. 

Personally, I do think it’s important, generally speaking, to do some intentional prayer around the time when you’re getting up for the day. The Scriptures say that God’s mercies are new every morning.[1]C.S. Lewis said, “Relying on God has to begin all over again every day as if nothing had yet been done.”[2]I also find it easier to create unhurried space in the morning. That being said, I think it’s also important to value flexibility by avoiding stringent rules. I do pray every day, although with two kids and a full schedule, it looks different from day to day. I make sure to dedicate longer times of prayer a couple of times throughout my week, wherever I can make it work. This works well for my introverted temperament, with its weekly pull to “get away from it all.” Discerning what works for you is part of your journey, and the consistent orientation of our lives around prayer, with discipline, is part of each of our journeys. As long as we remember that these are “connection times,” not just “times to get through a prayer,” we can come to prayer with anticipation, our feet fully outside of the hamster wheel of The Human Paradigm. The important thing is to see not that we have to pray but that we need to pray. 


Wherever works best! In the above passages from Luke, we see Jesus withdrawing to a deserted place, to a mountaintop, and to a place alone with his disciples. Clearly then, not all places are created equal. While we can pray everywhere, dedicated prayer happens more easily in certain places. 

Practicing in community of some sort is also important, as Jesus demonstrates with his disciples, taking them aside for dedicated times of prayer. A life liturgy (a spiritual order and structure to our days, weeks, months, and years) that involves regular prayer in community is an important anchor for our individual life before God. 

Again, it’s probably best not to be stringent with rules. Commitment, discipline, and dedication are the important things, no matter which structures best fit our lives, temperaments, and personalities.


Notwithstanding the fact that there’s no “one way” to pray, Scripture does give us clear and helpful guidelines. Nothing could be clearer, in fact, than what we call “The Lord’s Prayer,” which is one of the few times that Jesus answered a question with a clarion-clear answer.[3] 

Jesus makes it clear in the Sermon on the Mount (Matthew 5-7), of which the Lord’s Prayeris a part, that we are not to pray as the religious people of his day prayed. We are not just to memorize words or orations and then pray them loudly or at great length or for others to see, as if that impresses God. Many people approach God this way, through the perspective of The Human Paradigm, thinking they can appease or impress Him by doing the right dance steps, even if their heart is not in them. But the Father is interested in union, not in performance. So we are to pray with our hearts fully engaged. At the same time, Jesus does gives us words to pray, and words which are easily memorized. How then, can we take the words Jesus prayed and yet keep them from becoming rote? How can we approach with a both-and in mind, praying as Jesus taught us while also always keeping prayer fresh in our hearts?

The answer will involve praying with words in our heads but also coming to a place beyond words, where we are more in touch with our hearts than our heads. Prayer is a unique balance between these two realities, and moving into the heart is how we grow into the “always praying” posture that we see in Jesus. Sometimes we know what to pray, sometimes we don’t. Rather than seeing “not knowing what to pray” as bad, we can see our lack of knowing how to pray as a huge opportunity to get beyond ourselves and fall into God. 

For all of these readings in one place, order my book 'Learning to Live and Love Like Jesus.'

[1]Lamentations 3:22-23.

[2]C.S. Lewis, “A Letter to Mrs. L.” [June 6, 2017].

[3]Matthew 6:9-13; see also Luke 11:1-4.