Fear It Will Never Be Good Enough: Finding Freedom from Discontent

Do you ever feel like nothing in your life will ever be good enough? In today’s honest and insightful episode, Heather Creekmore opens up about her struggles with CDD or “Chronic Disappointment Disorder”—a feeling that no achievement or special day is ever truly satisfying. She explores the root of this persistent discontent and uncovers how fear, envy, and comparison play into our longing for "enough."

Heather dives deep into the heart-level issues fueling our dissatisfaction and shares practical wisdom on searching for true contentment in Christ. Drawing lessons from Tim Keller’s teachings on envy, Heather reveals how comparison, restlessness, and selfish ambition point us toward deeper spiritual problems, including idolatry. The episode is packed with personal stories, scriptural references, and actionable advice for anyone weighed down by the fear of never measuring up.

If you struggle with body image, success, or just feeling like you’re perpetually missing out, Heather walks you through how to identify envy, repent, and redirect your heart toward worship and gratitude. Ultimately, this episode is filled with hope—reminding us that our deepest satisfaction can only be found in Jesus and in the coming kingdom.

Episode Highlights:

• Personal stories of disappointment, from vacations to Mother's Day

• Discontent, envy, and their spiritual dangers

• How reslessness and comparison are more than just “bad habits”—they're rooted in envy

• The connection between body image, identity, and idolatry

• Scripture references: James 3:16, Galatians 5:19-21, 1 Corinthians 13:4, Proverbs 14:30

• Tim Keller’s two directions for overcoming envy: upward (fear of the Lord) and forward (hope in Christ for the future)

• The crucial role of repentance and confession—not just positive thinking

• Surrendering goals and desires to God for genuine change

• Turning discontent into worship and gratitude

Resources & Links:

• The Comparison Free Life by Heather Creekmore*

• 40 Day Body Image Workbook*

• Tim Keller’s Sermons on Envy (Listen here)

Connect with Heather:

• Compared to Who? Website

• Instagram

• Facebook

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