"Deeper"
Real Change for Real Sinners
by Dane Ortlund

Preparing Your Heart: Despair
The word "despair" typically has negative connotations. We're taught to avoid despair, to stay positive, to keep our chins up. But in this counter-intuitive chapter, you'll be invited to consider despair - specifically self-despair - as a necessary passage on the path to spiritual growth.
This isn't about wallowing in self-pity or unhealthy self-hatred. Rather, it's about the biblical pattern where emptiness precedes fullness, where death comes before resurrection. Throughout Scripture, we see this pattern: those who mourn are comforted, the poor in spirit receive the kingdom, those who humble themselves are exalted.
As you prepare to read this chapter, consider how naturally resistant we are to this downward journey. We want to skip past the valley of honest self-assessment and jump straight to victory and triumph. Yet time and again, Scripture tells us that the way up begins by going down. Growth comes through collapse - through the honest acknowledgment of our desperate need for grace.
This chapter may challenge your natural instincts, but it offers a deeply liberating truth: you don't need to pretend to be better than you are. The pathway to joy comes through the doorway of despair.
Before You Read
- What defenses or mechanisms do you tend to use to avoid facing the full reality of your sinfulness and weakness?
- How comfortable are you with the biblical pattern of "death before resurrection" in your own spiritual journey? Where might you be resisting this pattern?
Despair: The Strange Path Forward
This chapter explores a counterintuitive truth: the path to Christian growth often feels like going backward. Genuine spiritual progress requires us to pass through the door of self-despair.
The Necessity of Self-Despair
Throughout Scripture, we see a consistent pattern: those whose hearts are breaking are closest to God (Psalm 34:18). The low and destitute receive God's favor (Proverbs 3:34). Jesus teaches that death precedes life - "unless a grain of wheat falls into the earth and dies, it remains alone" (John 12:24).
This isn't because God wants us to feel bad about ourselves. Rather, it's because He desires our joy. He sends us down into honesty and sanity so we can see our sickness and run to the doctor.
The Sinfulness of Sin
To experience true growth, we must come face-to-face with who we really are apart from Christ. We tend to underplay our sinfulness, thinking "nobody's perfect" or "we all make mistakes." But our problem is deeper - we're running in the wrong direction.
We feel our need for growth only when we stack our condition next to God's infinite beauty and holiness.
Collapse and Resurrection
The pattern of Christian life is not a straight line upward but a curve down into death and thereby up into resurrection. We grow through collapse - through repentance and faith.
Discussion Questions
- Think about a time when something had to "die" or be let go of in your life before something better could emerge. What was that experience like? (This could be a relationship, a career path, a dream, or anything you had to surrender.)
- How comfortable are you with acknowledging the depth of your sinfulness?
- Have you experienced how "going down" into honest recognition of your sin has led to growth?
- What defensive mechanisms do you use to avoid fully facing your sin?
- Why is it so hard to "collapse" into Christ's arms when we fail?
- How might embracing this pattern of "death before resurrection" change your approach to spiritual growth?
Application
Set aside time this week for honest self-examination. Rather than generally acknowledging your sinfulness, identify specific patterns, attitudes, or behaviors that reveal your need for Christ. Confess these specifically, then meditate on how Christ's work directly addresses each one. Let your specific awareness of sin lead to specific appreciation of grace.