July 30, 2025

Rosanne Cash: Writing Masterclass from 4x Grammy Winner | How I Write

1 hour 7 minutes

I interviewed Rosanne Cash, a 4-time Grammy winner who's been writing songs for over 40 years. She's mastered something most writers struggle with: turning raw emotion into beautiful, lasting songs. She writes songs like a painter, starting with visual images, and brings the same rhythmic approach to both music and prose. We talked about how to turn pain into art, why anger and grief are powerful creative forces, how to deconstruct great songs to learn from masters like Bob Dylan, and how to develop your authentic voice through decades of deliberate practice. If you want to write with more emotional depth and turn life's difficulties into meaningful art, this conversation will show you how. Enjoy!

00:00:00 Why Great Writers Love Language Early

00:07:47 When to Ask for Feedback on Songs

00:14:46 How to Deconstruct Songs Like Bob Dylan

00:21:25 How to Study Different Songwriting Traditions

00:25:19 Why Truth Should Drive Your Creative Work

00:31:11 Why You Must Master Rhyme Schemes First

00:35:13 How to Use Anger as Creative Fuel

00:42:15 Why Emotions Are Invitations for Discovery

00:50:56 How Your Voice Changes Over Your Career

00:56:06 How Songs Start as Visual Images

01:01:25 Why Music Survives When Everything Else Dies

01:05:48 The Dream That Changed Everything About Art

Hey! I’m David Perell and I’m a writer, teacher, and podcaster. I believe writing online is one of the biggest opportunities in the world today. For the first time in human history, everybody can freely share their ideas with a global audience. I seek to help as many people publish their writing online as possible.

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