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

Hello Monday with Jessi Hempel

Careers, Business

4.8 • 1.1K Ratings

🗓️ 12 May 2025

⏱️ 33 minutes

🔗️ Recording | iTunes | RSS

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Summary

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.

Transcript

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0:00.0	LinkedIn News.
0:06.0	I've always pushed and pushed and pushed and pushed and failed and failed and then some success and then more pushing and more success and more failure.
0:16.0	And in the grand scheme of things, I have one notch more hope than I do shame.
0:25.5	A lot of times when you think about achievement, you know, people only see the end result.
0:31.4	They don't see the 20 years, the 30 years of toiling and obscurity or trying and failing and learning from the failure and then
0:40.1	trying something different.
0:44.5	From the news team at LinkedIn, I'm Jesse Hempel, and this is Hello Monday.
0:48.8	It's our show about work on our own terms.
0:53.9	I've got a real treat of an episode for you today. Today's show is about belonging.
1:00.1	It's about discipline and creativity, love, growth, but mostly it's about gardening. I have two
1:08.2	very special guests in the studio today, the power couple, Roxanne Gay,
1:13.1	and Debbie Milman. Now, both of these women have been in the studio before. In fact, they're responsible
1:17.9	for a couple of our most popular episodes. Debbie Milman brought us the vision exercise that we
1:24.4	return to almost every January 1st. She is a designer and a writer and a teacher.
1:31.0	She's host of Design Matters, which is a podcast that has been around since long before.
1:35.7	I really understood what the word podcast was.
1:38.5	She's the founder of the Masters in Branding Program at the School of Visual Arts.
1:43.8	Roxanne is also a writer and also a teacher, a professor, and she's a cultural critic.
1:50.1	She helps shape how we think in society about so many things like body image and race
1:55.4	and work to name just a few.
1:58.2	These two women have an incredible love story.
2:00.7	They met in 2018, moved in
	...

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