Book Club Questions for Cultivate

1.Casey opens by confessing that she spent years chasing a picture-perfect life — the right look, the right career, the right image — only to find herself empty. What is your version of that pursuit? What have you been striving after that has left you feeling more depleted than fulfilled?

2.She describes the moment she realized that 'making it happen' on her own terms was actually working against her. Have you had a similar moment of recognition — a point where your own striving clearly wasn't working? What did that feel like?

3.The gardening metaphor is introduced early as the book's central image. What is your instinctive reaction to that metaphor? Does it feel hopeful, frustrating, or something else — and why?

1.Casey describes her own life as cluttered — not just physically, but with commitments, expectations, and identities that were suffocating the things she actually valued. What forms of clutter are most present in your life right now? (Think beyond stuff — think time, relationships, mental noise.)

2.She talks about how we often clutter our lives with good things that crowd out the best things. Can you name a 'good thing' in your life that may actually be functioning as clutter right now — something that is preventing deeper growth?

3.Casey connects external clutter to internal clutter — the lies we believe, the fears we carry, the identities we have adopted that aren't truly ours. What internal 'clutter' do you most need to name and address?

1.Casey uses the image of breaking up hard, compacted soil as a metaphor for preparing our hearts and lives to receive growth. What does 'hard soil' look like in your life right now — areas that have become resistant, closed off, or difficult to work with?

2.She is honest that soil preparation is hard, slow, dirty work that yields no immediate visible reward. How do you typically respond to work that is necessary but invisible? Do you tend to skip it or embrace it?

3.Casey talks about the role of past pain, disappointment, and failure in compacting the soil of our lives. Is there a past experience — a loss, a betrayal, a failure — that has hardened a particular area of your heart, making it less receptive to growth?

1.Casey argues that most of us are planting things by default — by the habits, patterns, and yeses we drift into — rather than by intentional choice. What are you currently planting in your life by default that you haven't consciously chosen?

2.She uses her PowerSheets goal-setting tool as a framework for thinking intentionally about what we are planting. Even if you haven't used PowerSheets, what is your current process (if any) for choosing your goals and priorities? How intentional is it, really?

3.Casey asks readers to think about what they want their life to look like in ten years — not the perfect version, but the meaningful version. Take a moment to answer that question: What do you want to be true of your life, your relationships, and your character a decade from now?

1.Casey is candid about her own struggles with prayer — that it has felt dry, rote, or impossible to sustain. How would you honestly describe your current prayer life? Is it watering your life, or has it become more of an afterthought?

2.She talks about prayer as an act of dependence — an acknowledgment that we cannot grow anything of lasting value by ourselves. Why is dependence so hard for driven, goal-oriented people? Where does the resistance to dependence show up most in your life?

3.Casey shares how specific, written prayers helped her move from vague spiritual intentions to genuine, expectant conversation with God. Have you ever tried writing out your prayers? What might be gained by making prayer more concrete and recorded?

1.Casey describes how weeds in her garden were not obviously evil plants — they looked, at first glance, like they might belong there. What 'weeds' in your life currently look respectable or neutral but are actually stealing resources from what you are trying to grow?

2.She identifies comparison as one of the most insidious weeds — particularly in the age of social media. How does comparison function as a weed in your specific life? What does it steal from you when you allow it to grow unchecked?

3.Casey also names fear, people-pleasing, and perfectionism as common weeds. Which of these three has the deepest root system in your life? How long has it been growing there, and what has it cost you?

1.Casey describes the temptation to dig up a seed to check if it's growing — something every impatient gardener has done and every impatient person has done in their own life. What seeds have you dug up prematurely because you couldn't trust the process? What happened?

2.She makes the case that tending is active, not passive — it is the daily faithfulness of showing up, doing small things, and trusting that they matter. What small, unglamorous acts of tending are you being called to in this season of your life?

3.Casey writes about how our culture has conditioned us to expect instant results, and how that expectation damages everything from our relationships to our spiritual lives. Where do you feel the pull of 'instant results' most strongly? How has that expectation caused harm?

1.Casey's central phrase in this chapter is 'imperfect progress is still progress.' How does that simple reframe land on you? Does it feel like permission, like lowering standards, or like genuine wisdom?

2.She confesses that her pursuit of the perfect life was actually a form of control — a way of managing anxiety and maintaining the appearance of having it together. Can you relate to that dynamic? How has your own pursuit of perfect functioned as control or fear management?

3.Casey argues that perfectionism actually prevents growth because it causes us to abandon things that aren't going perfectly rather than tending them through the messy middle. Name a goal, project, or relationship that you have abandoned or neglected because it wasn't going perfectly.

1.Casey opens this chapter by acknowledging that true community is rare, and that many of us have settled for surface-level connection because vulnerability feels too risky. Where would you honestly place your current closest relationships on a spectrum from 'surface-level' to 'genuinely known'?

2.She talks about the way that isolation fuels comparison and perfectionism — without real community, we are left measuring ourselves against curated images rather than honest, messy human lives. How has isolation (even isolation in a crowd) fed perfectionism or comparison in your life?

3.Casey describes the difference between community that cheers you on in your goals and community that speaks truth into your life — that names your weeds, challenges your assumptions, and loves you enough to have hard conversations. Do you have both kinds of community? Which do you find easier to receive?

1.Casey shares her experience of pregnancy loss with striking vulnerability. How did her honesty in this chapter affect you? Did it open up something in your own experience of loss or grief?

2.She reflects that her hardest seasons — not her easiest — produced the deepest growth in her character and faith. Looking back at your own life, can you identify a hard season that, in retrospect, grew something significant in you that you couldn't have grown any other way?

3.Casey writes about the temptation, in hard seasons, to either rage at God or go completely numb to Him — and how she learned to keep tending even when tending felt pointless. Which of those two tendencies — rage or numbness — is more characteristic of how you respond to suffering?

1.Casey observes that many goal-oriented, driven people move directly from one harvest to the next planting without ever stopping to celebrate what has grown. Is this true of you? What is your relationship with celebration and gratitude for progress?

2.She frames celebration not as self-congratulation but as an act of worship — a way of acknowledging that God is the one who brings the harvest, and that gratitude is the right response. How does that reframe change the way celebration feels? Does it make it easier or harder to stop and celebrate?

3.Casey invites readers to look back over the whole of their lives and name specific harvests — things that have actually grown, relationships that have deepened, character that has been formed. Take a few minutes to do that exercise now: Name three specific 'harvests' in your life in the past few years.

1.Looking back across the entire book, which single chapter or concept was most personally significant to you? Why that one? What nerve did it touch that others didn't?

2.At the beginning of this study, you were invited to name one expectation and one fear you were bringing into the book. How has your thinking on those two things shifted — or not shifted — over the past eleven weeks?

3.Casey's central argument is that meaningful growth is cultivated — slow, intentional, and grace-filled — not manufactured by willpower or perfected by performance. How has your understanding of growth changed as a result of sitting with this argument across the whole book?