A decade before the so-called golden age of podcasting and exactly a year after the word “podcast” itself was timidly coined by The Guardian’s Ben Hammersley, Debbie Millman launched the world’s first podcast about design, armed with nothing more than an idea, a telephone line, and ample doggedness. Design Matters premiered on February 4, 2005. Over the years that followed, it evolved beyond design into the broader world of creative culture, featuring wide-ranging and deep conversations with celebrated designers, artists, writers, musicians, and other luminaries, including Chris Ware, Seth Godin, Maira Kalman, Dave Eggers, Kurt Andersen, Paola Antonelli, Malcolm Gladwell, John Maeda, Milton Glaser, Massimo Vignelli, Jonathan Harris, Chip Kidd, Dani Shapiro, Terry Teachout, Wendy MacNaughton, Jason Kottke, Ze Frank, Steven Heller, Grace Bonney, Marian Bantjes, Christoph Niemann, Dominique Browning, John Hockenberry, Barbara Kruger, and hundreds more. In 2011, the show received the People’s Choice Cooper Hewitt National Design Award. One of the most downloaded podcasts in the world today, it has shaped the public discourse on design and has inspired such newer projects as 99% Invisible and The Great Discontent.

Propelled at once by Moore’s Law and the pioneer spirit of exploring any new territory, the show’s early days were marked by that distinct blend of endearing technical embarrassments and visionary creative bravery. There is the bad audio quality, the atrocious commercial breaks, and the fact that Millman had to pay the network to put her show on the air — a pause-giving reminder of how low the barriers of entry have fallen, and how much we’ve come to take for granted.

But there are also boundlessly emboldening moments reminding us that the best kind of genius is one backed by goodwill, generosity, and pure human goodness. In an admirable antidote to our cancellation culture, graphic artist Shepard Fairey keeps his interview date despite having just had emergency eye surgery; he actually takes the call from his hospital bed to discuss, among other things, how having a baby daughter opened his eyes to the patriarchy’s oppressive impact and profoundly changed the kind of art he wanted to put into the world. In an uncommonly heartening conversation marking the fourth season premiere, mother-son writer duo Malcolm and Joyce Gladwell share the airwaves; when asked whether she was surprised by her son’s success in looking at what everyone looks at but seeing what no one sees, Joyce’s answer emanates the deep and disarming warmth of motherly love:

I was not [occupied with] fame and fortune… I wasn’t looking ahead very far — I was just enjoying the delightful child that had come into our life. He provoked mirth just by being who he was — by the way he moved, by the way he was made, by his eyes and his hair… Am I surprised? Yes and no. I can see the strands that contribute to Malcolm’s success, and to the way he thinks, the way he expresses himself. But I also am surprised at what it is he says and how he says it, and at how he got there — because there is no precedent for that.

Collected below are ten of my favorite episodes from the past ten years, along with my favorite highlights from each. You can subscribe to Design Matters here and catch up on the archive here.

DANI SHAPIRO (2014)

Dani Shapiro — whose memoir Still Writing: The Pleasures and Perils of a Creative Life is one of the very finest books on writing and the creative experience ever published — discusses our chronic flight from presence, how she wrote her way out of an existential crisis, and why vulnerability is the wellspring of all meaningful creative work. Listen on iTunes or below:

Deep inside, we are all so much the same — our details might be different, but we are all kind of walking the same internal path. And when I allow myself to be vulnerable, I am allowing myself to connect. I’m allowing people to connect to me. […] How do we actually be right here, right now? Not leaning toward the future, not leaning backwards into the past… How do we find a way to inhabit the moment more often than not? […] It’s the feeling of something becoming heightened in just a moment where … I know that it’s going into a place where it’s like it’s storing itself somewhere inside of me… It is unmistakable when it happens. And then sometimes … it requires a lot of patience to make sense of it. It’s not like that shimmer happens and, Eureka!, you have a story — it’s like that shimmer happens and, sometimes, it can be years before it connects to something else that then makes the story clearer, or makes clear why it shimmered.

MILTON GLASER (2010)

Legendary graphic designer Milton Glaser, creator of the iconic I♥NY logo and cofounder of the equally iconic New York Magazine, builds on his conversation with Millman from the 2007 book How to Think Like a Great Graphic Designer and discusses idealism, community, aging, the moral duties of the imagination, and what it takes to sustain one’s creative vitality over a long life. Listen on iTunes or below:

No one has the ability to understand our path until it is over, and if you can sustain your interest in what you are doing in your later years, you are very lucky. Many people get tired, indifferent, and defensive, and lose their capacity for astonishment… Daily life astonishes me. I’m looking through the door here, at the little table-and-chairs that was painted a light green and yellow, and there’s a plant on the table — a little pussy willow — and the combination is totally astonishing… Shadows in the night astonish me. And when you’re working, and you’re putting forms out on paper, every once in a while you’ll be astonished by what happens… The great thing about the work, and particularly work later in your life, is that you can still maintain the sense of possibility that at the end of the day you’ll know something that you didn’t know at the beginning of the day. And I just find that an extraordinary gift.

SETH GODIN (2014)

In this Design Matters Live conversation — occasional interviews recorded not in the studio but at various public events — the wise and wonderful Seth Godin discusses creative courage, the art of dancing with the Resistance, what defines great design, and his “children’s book for grownups” about vulnerability. See more transcribed excerpts and commentary here, then hear Millman’s 2007 studio interview with Godin here.

That is what [artists] do for a living — we dance with the Resistance, we don’t make it go away. You cannot make it go away — you cannot make the voice go away, you cannot make the fear go away, because it’s built in. What you can do is when it shows up, you say “Welcome! I’m glad you’re here. Let’s dance about this.” […] What we need to do is say, “What’s the smallest, tiniest thing that I can master and what’s the scariest thing I can do in front of the smallest number of people that can teach me how to dance with the fear?” Once we get good at that, we just realize that it’s not fatal. And it’s not intellectually realize — we’ve lived something that wasn’t fatal. And that idea is what’s so key — because then you can do it a little bit more. […] For the [creative person], what’s going on outside is trivial compared to what is going on inside… Don’t try to change the structure of the outside world [hoping that] then you’ll be fine, then you’ll be creative and then you’ll be brave. No. First, figure out how to be creative and brave and courageous, and the outside world will change on your behalf… It’s always the same case — it’s always the case of you’re a human, trying to connect to another human. And if you just pick one human that you can change for the better, with work that might not work — that’s what art is.

MALCOLM GLADWELL & JOYCE GLADWELL (2007)

Prolific author Malcolm Gladwell and his mother, Jamaican-born psychotherapist and writer Joyce Gladwell, discuss success, luck, racism, why we treat enduring ideas as disposable by letting timeless books go out of print (something I encounter regularly and find particularly unsettling), and more. Listen on iTunes or below:

When I think about my family, I think of us as being “serial outsiders”… I have a mother who moved from Jamaica to England — [and] the cultural distance between those two points is greater than the physical difference between those two points — then married an Englishman and moved to Canada (and not just to Canada — to a little rural corner of Ontario filled with Mennonites), and then I went from there and moved to the United States, to New York City. So when I say we’re “serial outsiders” I mean we’ve replicated the role of the outsider over and over again. And my writing is the writing of an outsider — it’s the writing of an observer… The outsider always has an enormous advantage in terms of seeing things in a different way… It doesn’t have to do, necessarily, with any particular gift of the outsider him- or herself — it’s the gift of the position of being on the outside. You literally see something differently when you look from outside the house than when you look from inside the house. So, in that sense, I’m the lucky recipient of that series of circumstances. […] What I like to do in my writing is combat the feeling one has of bafflement, which I think is a disconcerting feeling… I don’t think I can promise in my writing the answers to problems, but I can promise something which is probably more important in … combatting the sense of unease we have in the world… I can help people to understand how to think about things. That’s what we really want. We’re not unhappy with the fact that the world presents lots of different, difficult-to-answer problems — we’re unhappy about the fact that we don’t even know how to start to think about all these things, what kind of framework to use, what questions to ask, where the beginning point is and where the end point is to any kind of process of analysis. My writing is really intended to be that kind of a roadmap — and I find those kinds of roadmaps to be enormously comforting.

RACHEL SUSSMAN (2014)

Artist Rachel Sussman discusses her decade-long project The Oldest Living Things in the World — which produced one of the best books of 2014 — and its underlying questions about permanence, impermanence, deep time, and how we orient ourselves to the universe. Listen on iTunes or below:

It’s hard to answer [whether any of these ancient organisms have consciousness]. I mean, no, I don’t literally think that they have a consciousness. But at the same time I think there is a sort of “world spirit” — which I say to you as an atheist. Nature is a system, and these organisms are part of that — and I think there is a strong will to live. And [yet], these are all terms that we just impose upon these things.

PAOLA ANTONELLI (2006)

Curator extraordinaire Paola Antonelli offers a behind-the-scenes look at her uncommonly visionary MoMA shows exploring safety, the humble masterpieces of everyday life, and the intersection of design and technology, and discusses the glories of living in New York City, the tyranny of the corporate world on our inner lives, and what we can do to create degrees of freedom even within limiting systems. Listen on iTunes or below:

Designers’ humility will change the world… Designers just sit and think about how to make people’s lives better. And to do so, you have to strip yourself of your ego for a moment and put yourself in other people’s shoes — the first act of real humanity. And it takes humility.

SHEPARD FAIREY (2007)

Graphic artist Shepard Fairey — who has used the raw materials of capitalism and freedom to continually challenge our social, political, and personal assumptions about how the world works and to offer sometimes subtle, sometimes provocative ideas on how it can work better — discusses how he went from covering his neighborhood in stickers to being one of the world’s most prominent street artists, how the notion of “selling out” impoverishes our understanding of creative culture, and what his daughter’s birth taught him about our world. Listen on iTunes or below:

Here’s how having a child has affected my art: I think that in society, much of the time, the male, dominant, aggressive, I’m-gonna-make-my-way-and-rule-things mentality is rewarded, and the maternal side of things is definitely not valued as much… It’s a patriarchal society. But seeing how my wife is with our daughter and realizing how much work it is … and that it’s our yin and yang that allows the family unit to function in a really amazingly positive way, I really tapped into more of my feminine side, appreciating more the maternal side of things… A lot of the work that I’ve been doing is dealing with peace and using a lot of female figures. One of the things I’ve thought about was [that] it’s usually men that perpetuate injustice, and they take up arms to do so. And when women take up arms, I think they do it to correct an injustice. (This is a generalization, of course… There are people like Margaret Thatcher out there.) … A lot of the work that I was doing [was] as agitational and provocative as possible. Now, I still try to make the work really engaging and provocative, but also allow beauty, the merit of beauty and the maternal side of things to show through in some of the elements in my work.

SOPHIE BLACKALL (2012)

Artist, author, and children’s book illustrator Sophie Blackall — creator of such wondrous treasures as The Mighty Lalouche and The Baby Tree — discusses the necessary balance of optimism and subversiveness in children’s books, her immeasurably charming Missed Connections project, and the challenges and rewards of illustrating Aldous Huxley’s only children’s book. See more highlights here and listen on iTunes or below:

SB: I think children are pretty subversive creatures. DM: It’s interesting: It’s subversive in the way that The Wizard of Oz is subversive — there’s a subtext. And that subtext has to do with love, and longing, and loss, and pain. But I guess, for me, there seems to be an innate optimism that doesn’t feel dark — yes, there’s darkness in the work, but I always get the sense that the light overcomes that darkness. … You can create a brush stroke that somehow defines wistfulness. But in that ability to see that wistfulness, I can’t help but feel understood — which … then gives me a great sense of joy.

CHRIS WARE (2012)

Chris Ware — one of the finest cartoonists of our time and a frequent New Yorker cover artist — discusses his intricate and immensely brilliant book-in-a-box Building Stories, why it’s necessary to make room for sadness in the fabric of life, and how storytelling gives shape to the human experience. Find more highlights here and listen on iTunes or below:

When I was in school, some of my teachers told me, “Oh, you can’t write about this or that, you can’t write about women, because then you’re colonizing them with your eyes”… And that seems ridiculous to me… That’s what writing is about — it’s about trying to understand other people. […] It really all comes down to empathy… If you feel empathy for a group of people or a nation, you’re less likely to attack them. And I just feel like it’s what being human is — that’s the most important thing you can learn, it’s the most important thing you can impart to a child.

MAIRA KALMAN (2007)

The ceaselessly prolific and imaginative artist and author Maira Kalman — whose spectacular recent memoir of sorts, My Favorite Things, was among last year’s best books — discusses the essential role of boredom in creativity (something eloquently expounded by Søren Kierkegaard, Bertrand Russell, and Adam Phillips) and why storytelling for children shouldn’t be approached as a special species of storytelling different from that for adults (something memorably asserted by J.R.R. Tolkien, C.S. Lewis, Maurice Sendak, and Neil Gaiman). Listen on iTunes or below:

Boredom and impatience are real motivators. I don’t want to do one thing all the time — I’m “multi-curious.” And, really, not knowing how to do something and then not being afraid to do it is a nice combination — because you just try new things. If you’re open to whatever serendipity of inspiration is around, sometimes you find yourself sewing and sometimes you find yourself playing imaginary viola. But I don’t like having a different mindset for children than I do for adults. I just would like to tell the story that’s around me, and just kind of chronicle what I see — and it shouldn’t matter if it’s an adult or a child… What’s the worst that can happen is you can fail — or it can be bad. (Which has happened.) And yet, somehow, the world doesn’t come to an end. So I’m ultimately very brave and terrified… It’s the human condition.

WENDY MACNAUGHTON & CAROLINE PAUL (2013)

Artist Wendy MacNaughton — a Brain Pickings regular — and writer Caroline Paul discuss their endlessly wonderful and layered book Lost Cat, how they balance their romantic relationship with their creative collaboration, our chronic compulsion for control, and what true love really means. See more highlights here and on iTunes or below:

You cannot know everything about the creature that you love, and you also can’t control that relationship. And maybe that’s okay — because we can’t control relationships. In fact, if we did control them to the degree that we want, it would probably provide us with nothing. Relationships are probably our greatest learning experiences.

To see what the next decade of stimulating and ennobling conversations brings, subscribe to Design Matters here, then explore the archive here.