12-Week Study & Discussion Guide

Praying Like Monks, Living Like Fools

by Tyler Staton·96 discussion questions

Lead your group with the discussion already prepared: a reading plan, thoughtful questions, and printable handouts for everyone.

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Week 1 — FreeRead the Introduction of Praying Like Monks, Living Like Fools. Primary passages: Matthew 6:5–13; Luke 11:1–4.

Discussion question your group will work through:

1.Staton describes prayer as simultaneously "the source of Jesus's most astonishing miracles and the subject of Jesus's most audacious promises." Yet most people find it boring, obligatory, or confusing. Which of those three words — boring, obligatory, or confusing — best describes your own relationship with prayer right now, and why?

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About This Study Guide

At a glance: this is a 12-week study and discussion guide for Praying Like Monks, Living Like Fools by Tyler Staton, with 96 questions organized by reading assignment. Week 1 is free to read, with no card required.

Tyler Staton's Praying Like Monks, Living Like Fools begins with an honest confession: prayer is the thing Jesus talked about most confidently and most of us practice most awkwardly. As national director of the 24/7 Prayer movement and lead pastor of Bridgetown Church in Portland, Oregon, Staton writes from both the heights of contemplative tradition and the mess of ordinary life. His thesis is deceptively simple — prayer is not a spiritual discipline to be mastered but a relationship to be inhabited, and the postures of historic Christian prayer (silence, lament, confession, persistence, wonder, and more) are not techniques for the advanced but gifts for the desperate. The title captures the tension at the heart of the book: monks pray with radical intentionality, fools live with radical trust, and Jesus calls his followers to both.

This study guide is designed for use over twelve weeks, either in a small group or as a personal devotional journey. The pattern for each week is straightforward: read the assigned chapter before your meeting or study time, spend a few minutes journaling your initial reactions, then work through the discussion questions either alone or with others. You do not need to answer every question — let the ones that create friction or curiosity lead the conversation. Each week closes with a prayer drawn from the language and imagery of that chapter; use it as a launching pad for your own words rather than a script to be read robotically.

By the end of this guide, you will not have become an expert on prayer — and Staton would be the first to say that is not the goal. What you can expect is a more honest relationship with God, a vocabulary for the full range of prayer postures, and the quiet courage to bring your actual self — doubts, disappointments, longings, and all — before the One who has been listening all along.

Week 1: Introduction — The Gift Nobody Wants

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Read the Introduction of Praying Like Monks, Living Like Fools. Primary passages: Matthew 6:5–13; Luke 11:1–4.

Staton opens by naming the gap most of us feel but rarely admit — that prayer is supposed to be the center of the Christian life, and yet it so often feels like the most burdensome obligation on our list. Come to these questions willing to be honest about where you actually are.

1.Staton describes prayer as simultaneously "the source of Jesus's most astonishing miracles and the subject of Jesus's most audacious promises." Yet most people find it boring, obligatory, or confusing. Which of those three words — boring, obligatory, or confusing — best describes your own relationship with prayer right now, and why?

2.The title *Praying Like Monks, Living Like Fools* sets up a creative tension. In your own words, what do you think Staton means by each half of that phrase? What kind of person do you imagine when you picture each one?

3.Staton introduces the idea that prayer is "a search for help outside the self" (a phrase that John Mark Comer calls the most important statement for our time). What does it reveal about us — and about our culture — that we find it so hard to ask for help outside ourselves?

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Group handout: Praying Like Monks, Living Like Fools

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Week 2: Chapter 1 — Ordinary Mystics

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Read Chapter 1 of Praying Like Monks, Living Like Fools. Primary passages: Luke 18:1–8; 1 Thessalonians 5:16–18.

1.Staton argues that the monastic tradition of prayer was never meant to be kept inside monastery walls — it was always meant to spill out into everyday life. Does that idea feel liberating or does it raise questions for you about whether "ordinary" life can really be a place of deep prayer?

+ 7 more questions in the full guide

Week 3: Chapter 2 — Silence

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Read Chapter 2 of Praying Like Monks, Living Like Fools. Primary passages: Psalm 46:10; 1 Kings 19:11–13.

1.Staton opens the chapter by observing how uncomfortable most modern people are with silence — we fill every gap with a screen, a playlist, or a notification. When was the last time you sat in genuine silence? What happened inside you?

+ 7 more questions in the full guide

Week 4: Chapter 3 — Unanswered Prayer

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Read Chapter 3 of Praying Like Monks, Living Like Fools. Primary passages: Matthew 7:7–11; 2 Corinthians 12:7–10.

1.What is the unanswered prayer that has done the most damage to your prayer life? You don't have to share all the details, but name the category — healing, relationships, provision, direction. How long have you been carrying it?

+ 7 more questions in the full guide

Week 5: Chapter 4 — Lament

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Read Chapter 4 of Praying Like Monks, Living Like Fools. Primary passages: Psalm 22; Lamentations 3:1–26.

1.Staton notes that roughly one-third of the Psalms are laments — the largest single category in Israel's hymnbook. Does that proportion surprise you? What does it say about what God considers acceptable prayer?

+ 7 more questions in the full guide

Week 6: Chapter 5 — Confession

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Read Chapter 5 of Praying Like Monks, Living Like Fools. Primary passages: Psalm 51; James 5:16; Luke 15:11–24.

1.How have you typically thought about confession — as punishment, as obligation, as relief, or as something else? Where did that understanding come from? How does it compare to the way Staton frames it?

+ 7 more questions in the full guide

Week 7: Chapter 6 — Intercession

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Read Chapter 6 of Praying Like Monks, Living Like Fools. Primary passages: Romans 8:26–27, 34; John 17:6–26.

1.Who are the people currently on your regular prayer list — if you have one? When you think about praying for others, what emotions come up? Obligation? Love? Uncertainty about whether it actually makes a difference?

+ 7 more questions in the full guide

Week 8: Chapter 7 — Persistence

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Read Chapter 7 of Praying Like Monks, Living Like Fools. Primary passages: Luke 18:1–8; Genesis 32:22–32.

1.Think of a prayer you have been praying for a long time — months, years, perhaps decades. What has that long waiting done to your faith? Has it deepened your trust, eroded it, or something more complicated than either?

+ 7 more questions in the full guide

Week 9: Chapter 8 — Wonder

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Read Chapter 8 of Praying Like Monks, Living Like Fools. Primary passages: Psalm 8; Romans 1:20; Matthew 6:28–30.

1.Staton opens the chapter with an observation about how familiarity kills wonder — we stop seeing what we see every day. Think about something in your life right now — a relationship, a place, a physical sensation — that you have stopped seeing with fresh eyes. What would it take to see it again?

+ 7 more questions in the full guide

Week 10: Chapter 9 — The Prayer of Examen

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Read Chapter 9 of Praying Like Monks, Living Like Fools. Primary passages: Psalm 139:23–24; Luke 24:13–35.

1.Before reading about the Examen, how did you typically end your days in terms of reflection or prayer? Did you review your day with God, or did the day simply end and the next one begin?

+ 7 more questions in the full guide

Week 11: Chapter 10 — A Life of Prayer

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Read Chapter 10 (and any Conclusion) of Praying Like Monks, Living Like Fools. Primary passages: Colossians 4:2; Acts 2:42–47; Revelation 5:8.

1.Staton's closing chapters move from individual prayer practices to the vision of a community shaped by prayer — like the early church in Acts 2, which devoted itself to prayer as a communal, corporate act. How does your current community reflect that vision? Where does it fall short, and what would need to change?

+ 7 more questions in the full guide

Week 12: Review & Reflection — The Whole Journey

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No new reading this week. Review your notes, journal entries, and any highlighted passages from Praying Like Monks, Living Like Fools.

1.Go back to the sentence you wrote in Week 1 about what you hoped to find or experience by the end of this study. Read it now. How would you answer that hope? What did you find that you were looking for? What did you find that surprised you?

+ 7 more questions in the full guide

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About the Praying Like Monks, Living Like Fools guide

How many weeks is the Praying Like Monks, Living Like Fools study guide?

This study guide covers Praying Like Monks, Living Like Fools in 12 weeks, with week-by-week discussion questions, reading references, and closing prayers for each session.

How many discussion questions are included?

The complete guide includes 96 discussion questions across 12 weeks — an average of 8 questions per week, designed for group conversation.

Can I use this guide for a book club?

Yes — the questions are written for group discussion and work well for small groups, book clubs, church studies, and couples reading together.

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