13-Week Study & Discussion Guide

The Life You've Always Wanted

by John Ortberg·97 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 The Life You've Always Wanted. Key passage: Matthew 11:28-30.

Discussion question your group will work through:

1.Ortberg opens with a vision of what it might look like to be genuinely transformed — not just to behave differently, but to actually become different. How would you describe, in your own words, the 'life you've always wanted'? What images or longings come to mind?

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About This Study Guide

At a glance: this is a 13-week study and discussion guide for The Life You've Always Wanted by John Ortberg, with 97 questions organized by reading assignment. Week 1 is free to read, with no card required.

John Ortberg's The Life You've Always Wanted is a warm, honest, and deeply practical guide to spiritual transformation through the classic Christian disciplines. But Ortberg is careful from the very first pages to reframe what spiritual disciplines are actually for: they are not a performance track for the spiritually elite, nor a checklist that earns God's approval. They are, as Ortberg puts it, a way of "training" rather than merely "trying" — the difference between a person who strains to run a marathon on willpower alone and one who has patiently built the capacity to run it with joy. The book's central argument is that the life we most deeply long for — a life of love, peace, meaning, and genuine Christlikeness — is not achieved by trying harder but by arranging our lives around the practices that open us to God's transforming grace. The compass of the whole journey is Jesus himself: what he was like, how he lived, and who we become as we are drawn closer to him.

This study guide is designed to help you move through the book one chapter at a time, whether on your own or with a small group. The recommended rhythm is simple: read the assigned chapter before your meeting, spend a few minutes journaling your honest reactions, and then work through the discussion questions together — or, if you're studying alone, use them as prompts for prayer and reflection. Don't rush. Ortberg writes with humor and vulnerability, and the best thing you can do is slow down enough to let his stories and challenges land in your own life.

By the end of this guide, you should expect more than new information about spiritual disciplines — you should expect a genuine shift in how you think about spiritual growth. You will have examined your own "soul's condition," confronted the gap between the life you are living and the life you were made for, and taken concrete steps toward practices that open you to change. Most importantly, you will have kept your eyes fixed on the person of Jesus Christ, whose life is the blueprint and whose grace is the power for everything this book describes.

Week 1: Introduction — Invitation to a Changed Life

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Read the Introduction of The Life You've Always Wanted. Key passage: Matthew 11:28-30.

Before diving into any discipline, Ortberg invites us to sit with a single question: what is the life we have always wanted, and do we actually believe it is available to us?

1.Ortberg opens with a vision of what it might look like to be genuinely transformed — not just to behave differently, but to actually become different. How would you describe, in your own words, the 'life you've always wanted'? What images or longings come to mind?

2.Ortberg distinguishes between 'trying' and 'training' as two very different approaches to spiritual growth. In your own life, which approach have you most often used? What has that looked like in practice?

3.He uses the illustration of a person trying to run a marathon without training — straining on race day but never building capacity beforehand. Where else in life do you see this same pattern of trying without training? Have you seen it in your spiritual life?

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Group handout: The Life You've Always Wanted

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13-Week Schedule

  1. Week 1Introduction — Invitation to a Changed Life7 questions
  2. Week 2Chapter 1 — Surprised by Change8 questions
  3. Week 3Chapter 2 — Training vs. Trying8 questions
  4. Week 4Chapter 3 — The Genius of Jesus7 questions
  5. Week 5Chapter 4 — A Slow and Certain Light (The Practice of Slowing)8 questions
  6. Week 6Chapter 5 — Interrupted (The Practice of Serving)7 questions
  7. Week 7Chapter 6 — An Unhurried Life (The Practice of Solitude)8 questions
  8. Week 8Chapter 7 — Appropriate Confidence (The Practice of Prayer)8 questions
  9. Week 9Chapter 8 — Receiving Grace (The Practice of Confession)7 questions
  10. Week 10Chapter 9 — Abundant Simplicity (The Practice of Simplicity and Secrecy)7 questions
  11. Week 11Chapter 10 — Dirty Fingernails (The Practice of Suffering and Perseverance)7 questions
  12. Week 12Chapter 11 — A Life of Reckless Love (The Practice of Community)7 questions
  13. Week 13Review & Reflection — The Life That Can Be Yours8 questions

Week 2: Chapter 1 — Surprised by Change

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Read Chapter 1 of The Life You've Always Wanted. Key passage: 2 Corinthians 3:18.

1.Ortberg points to the gap between the spiritual lives Christians often claim and the spiritual lives they actually live. When you look honestly at your own life, where do you notice that gap most painfully?

+ 7 more questions in the full guide

Week 3: Chapter 2 — Training vs. Trying

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Read Chapter 2 of The Life You've Always Wanted. Key passages: 1 Timothy 4:7-8; 1 Corinthians 9:24-27.

1.Ortberg's central metaphor is athletic training. Just as a runner doesn't run a marathon by trying hard on race day, a Christian doesn't become patient or loving merely by gritting her teeth in the moment. How does this image land for you — does it feel liberating, challenging, or both?

+ 7 more questions in the full guide

Week 4: Chapter 3 — The Genius of Jesus

All 7 questions →

Read Chapter 3 of The Life You've Always Wanted. Key passages: Matthew 5-7 (Sermon on the Mount); John 1:14.

1.Ortberg argues that Jesus was not only morally perfect but also extraordinarily brilliant, joyful, and fully alive. How does this portrait of Jesus differ from the images of Jesus you grew up with or most commonly encounter?

+ 6 more questions in the full guide

Week 5: Chapter 4 — A Slow and Certain Light (The Practice of Slowing)

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Read Chapter 4 of The Life You've Always Wanted. Key passages: Psalm 46:10; Luke 10:38-42.

1.Ortberg quotes an older mentor who told him, 'You must ruthlessly eliminate hurry from your life.' What is your honest reaction to that statement? Does it feel freeing, impossible, or somewhere in between?

+ 7 more questions in the full guide

Week 6: Chapter 5 — Interrupted (The Practice of Serving)

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Read Chapter 5 of The Life You've Always Wanted. Key passages: Mark 10:42-45; John 13:1-17.

1.Ortberg describes how Jesus redefined greatness — not as authority over others but as service to others. How does this redefinition challenge the values of the culture you live and work in? How does it challenge your own instincts?

+ 6 more questions in the full guide

Week 7: Chapter 6 — An Unhurried Life (The Practice of Solitude)

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Read Chapter 6 of The Life You've Always Wanted. Key passages: Mark 1:35; Luke 5:16; Matthew 14:23.

1.Ortberg notes that Jesus consistently withdrew to solitary places to pray — even in the busiest seasons of his ministry. What does it tell us about Jesus' relationship with the Father that he needed these times of withdrawal? What does it tell us about our own need for solitude?

+ 7 more questions in the full guide

Week 8: Chapter 7 — Appropriate Confidence (The Practice of Prayer)

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Read Chapter 7 of The Life You've Always Wanted. Key passages: Matthew 6:5-13; Luke 11:1-4; Romans 8:26.

1.Ortberg is honest that many Christians are disappointed with their prayer lives — prayer feels dutiful, rote, or one-sided. Does this resonate with your experience? What has your relationship with prayer actually been like, honestly?

+ 7 more questions in the full guide

Week 9: Chapter 8 — Receiving Grace (The Practice of Confession)

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Read Chapter 8 of The Life You've Always Wanted. Key passages: James 5:16; Psalm 32:1-5; 1 John 1:9.

1.Ortberg argues that we live in a culture of image management — we constantly curate how we appear to others, and often to ourselves. How does this culture make the practice of honest confession feel threatening or strange?

+ 6 more questions in the full guide

Week 10: Chapter 9 — Abundant Simplicity (The Practice of Simplicity and Secrecy)

All 7 questions →

Read Chapter 9 of The Life You've Always Wanted. Key passages: Matthew 6:19-24; Luke 12:15-21.

1.Ortberg describes how our possessions can quietly begin to possess us — how accumulation creates anxiety rather than security. Does this ring true in your own experience? What possessions, roles, or achievements do you find yourself most anxious about losing?

+ 6 more questions in the full guide

Week 11: Chapter 10 — Dirty Fingernails (The Practice of Suffering and Perseverance)

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Read Chapter 10 of The Life You've Always Wanted. Key passages: Romans 5:3-5; James 1:2-4; 2 Corinthians 4:17.

1.Ortberg is frank that suffering is not one of the disciplines we get to schedule. It arrives uninvited. What is your honest, gut-level response to the idea that God might use pain and hardship as instruments of transformation in your life?

+ 6 more questions in the full guide

Week 12: Chapter 11 — A Life of Reckless Love (The Practice of Community)

All 7 questions →

Read Chapter 11 of The Life You've Always Wanted. Key passages: John 13:34-35; 1 Corinthians 13; 1 John 4:7-12.

1.Ortberg calls love a discipline — not just a feeling or a spiritual gift we either have or don't. What does it mean to practice love as a discipline? What does that practice look like on a Tuesday morning with difficult people in your life?

+ 6 more questions in the full guide

Week 13: Review & Reflection — The Life That Can Be Yours

All 8 questions →

Review your notes and journal from the entire study. Re-read any passages that were particularly meaningful to you.

1.As you look back across the entire book, which chapter or discipline had the greatest personal impact on you? What made it land so powerfully?

+ 7 more questions in the full guide
Book Club QuestionsMore by John OrtbergSpiritual Growth & DisciplinesChristian LivingFor Small GroupsFor Individual StudyFor ChurchesFree Question GeneratorMake a reading schedule for this book

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About the The Life You've Always Wanted guide

How many weeks is the The Life You've Always Wanted study guide?

This study guide covers The Life You've Always Wanted in 13 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 97 discussion questions across 13 weeks — an average of 7 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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