Debbie Millman & Roxane Gay on Love, Creativity, and the Discipline to Grow

Hello Monday with Jessi Hempel

Debbie Millman and Roxane Gay know a thing or two about building creative lives. Debbie is a legendary designer, writer, and podcast host. Roxane is a bestselling author and cultural critic. Together, they’ve built a partnership rooted in discipline, love, and slow growth. On this week’s episode of Hello Monday, Jessi Hempel welcomes the couple back to the studio to talk about their new book, and what it really takes to live a meaningful creative life.

Their book, Love Letter to a Garden, is both literal and metaphorical. It’s about vegetables, sure. But it’s also about how we learn, how we fail, and how we grow. Debbie shares stories of her journey from struggling gardener to seasoned grower, an arc that mirrors her creative life. Roxane contributes recipes she’s crafted using the produce Debbie grows.

Jessi, Debbie, and Roxane dig into the kind of growth that takes time, and the work required to nurture it.

They discuss:

• The invisible years behind every “overnight” success

• How to keep going when you fail again and again

• Why your hope must be slightly bigger than your shame

• What it means to save your best energy for what matters most

• The difference between meaningful work and making work your meaning

Continue the conversation with us at Hello Monday Office Hours! Join us here, on the LinkedIn News page, this Wednesday at 3 PM EST.