6. Why We Don’t Know How to Lament

What if the pain you’re avoiding is actually the path to healing?
And what if God already gave you the words for it?

In Part 2 of this conversation, John Ortberg and Rankin Wilbourne explore one of the most overlooked practices in the Christian life: lament.

If the Psalms are the prayer book of God’s people, why are so many of them… sad? And why do we avoid praying that way?

You’ll discover:
- Why lament is essential (not optional) in spiritual life
- How lament becomes a bridge between pain and trust
- Why avoiding pain actually deepens it
- A practical way to pray honestly without getting stuck in despair

This is Part 2 of a 3-part conversation on learning to pray your emotions.

📚 Today's Resources:

A Grief Observed — C. S. Lewis (indirect thematic reference)
Naming the Silences — Stanley Hauerwas

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00:00 – Picking Up the Conversation (Part 2)
00:21 – Why the Psalms Are Full of Sad Songs
01:17 – 30–70% of Psalms Are Laments
01:44 – “How Long, O Lord?” (Psalm 13)
02:14 – What Lament Reveals About Life
02:40 – Why We Resist Lament
03:06 – What Lament Actually Is
03:36 – Permission to Bring Everything to God
04:08 – Do You Pray Like This?
04:31 – Image 1: Running Toward the Storm (Buffalo)
05:31 – Why Avoiding Pain Makes It Worse
06:04 – The Paradox of Grief
06:34 – Image 2: Lament as a Bridge
06:59 – From Pain → Trust (Psalm 13 Turn)
07:38 – How Psalms Train Us to Trust
08:04 – When Prayer Turns Into Rumination
08:52 – Using Psalms as Scaffolding
09:43 – Why Lament Doesn’t Leave You Stuck
10:11 – Learning the “Turn” to Trust
10:46 – Rehearsing Trust Like a Song
11:13 – Naming the Silences
11:48 – Training Your Heart Through Prayer
12:13 – Guided Prayer (Psalm 5)
12:58 – Key Takeaways + Preview Part 3