The Average Pursuit

I've Failed Too Many Times—What Now?


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Host: Jonathan Sheppard
Special Guest: Callie Sheppard

In this deeply vulnerable episode of The Average Pursuit, my wife Callie joins me to talk about a season in our life when we felt like we had failed as parents. She opens up about the shame she carried and the moment she thought it was too late for restoration.

Together, we walk through how God met us in the middle of that brokenness and brought hope, healing, and a fresh start. If you’ve ever felt like your mistakes define you or that you’ve failed one too many times, this conversation is for you.

You’ll hear:

  • What shame can do to your heart when you feel you’ve failed

  • How God’s grace restores and recommissions us, even in our lowest moments

  • Practical ways to take your next step toward healing and restoration

  • Encouragement straight from Scripture (John 21, Romans 8:1, Psalm 34:18)

Key takeaway: Your failure is not the final word. Jesus is.

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  • "Shame doesn’t just make you feel like you did something wrong—it makes you believe you are the mistake. But God’s truth says otherwise."

  • "Your failure doesn’t disqualify you. God doesn’t waste your pain; He redeems it."

  • "Peter thought his story was over when the rooster crowed, but Jesus was just getting started."

Share this episode with someone who needs hope today!

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The Average PursuitBy Jonathan Sheppard