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EXPECTATION VS. REALITY
Disappointment with Myself | Part 4
Senior Pastor Keith Stewart
January 25, 2026

Many of us carry regret over past decisions, failures, or missed opportunities—and we’re often harder on ourselves than anyone else. In “Disappointment With Myself” (Expectations vs Reality – Part 4), Pastor Keith Stewart explores why our past keeps intruding on our present and how the gospel frees us from shame, false guilt, and self-condemnation. You’ll discover why God is not disappointed in you and how real change begins by accepting God’s acceptance. If you’re ready to stop living under regret and start living from grace, this message is for you.

1. What part of the message felt most “for you” right now, why?

2. Which kind of backward-looking thinking do you struggle with most: woulda (decisions), coulda (failures), or shoulda (expectations)? What does it typically sound like in your head?

3. The message distinguishes examination from rumination. What’s a practical sign that you’ve crossed the line from learning to self-punishing?

4. Where do you most feel false guilt (expectations from others, old “shoulds,” perfectionism)? How can you tell the difference between conviction and condemnation in your own experience?

5. The message says, “God is never disappointed,” because disappointment includes surprise and frustration. How does that idea challenge or heal your view of God? What makes it hard to believe?

6. What does it look like, concretely, to “send your past packing” this week? (One habit, one conversation, one confession, one boundary, one step of repair.)

7. “Seek progress, not perfection.” Where do you need to apply that in your spiritual life, relationships, habits, or recovery?

8. “Before we can become who we will be in Christ, we must accept who we are in Christ.” What’s one identity statement from Scripture you need to rehearse daily right now?