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Book Summary: Why Design Matters – Conversations with the World’s Most Creative People

Why Design Matters (2022) is a collection of some of the best interviews from Debbie Millman’s long-running podcast of the same name. It collects over 50 interviews from over 15 years’ worth of conversations. These talks not only explain why design matters, they also show how the principles of design extend to creativity in general and the ways in which we communicate and express ourselves.

Who is it for?

  • Anyone interested in the creative process
  • People fascinated by design and marketing
  • Artists looking for inspiration

Book Summary: Why Design Matters - Conversations with the World's Most Creative People

What’s in it for me? Get inspired by the words and wisdom of America’s creative giants.

Since 2005, Debbie Millman has been regularly sitting down with some of the brightest creative minds around to talk about their lives and their work. Some of these people have been major players in the world of graphic design, but these days Millman is just as likely to sit down with a writer or a Broadway director as she is an illustrator or graphic artist. As you’ll soon learn, design is everywhere. It’s on the page, it’s on the stage and the screen, it’s in the clothes you wear and on the packaging of the food you buy. Design is ultimately about communicating ideas. It’s the stuff of art, creativity, and life.

Book Summary: Why Design Matters - Conversations with the World's Most Creative People

In these summaries, you’ll learn

  • how limitations can spark creativity;
  • that drawing can be a universal language; and
  • why you should learn to dance with your fears.

Design matters because design is a powerful tool for communication.

If you know anything about the history of graphic design, you’re probably familiar with the name Milton Glaser.

Glaser is indeed one of the legends of the business, having cofounded New York magazine and designed some of the most iconic images of the sixties and seventies, including the “I Love New York” logo. His name is synonymous with design. Another part of what makes Glaser such a legendary figure is that he’s also spent a lot of time thinking about why design matters. In fact, he wrote an influential article titled “12 Steps on the Designer’s Road to Hell.”

In it, Glaser lists many of the tough decisions designers have to consider during the course of their careers. These are such important decisions that Glaser considers each one either a step toward or out of hell. Why? Well, it comes down to the simple fact that a designer is communicating with the public. Everything from a carton of milk to a presidential campaign contains elements of design that were thought out by someone. And, as we all know, some of these designs are made to intentionally misrepresent. Maybe they’re intended to make the product look bigger on the shelf or that they’re healthier than they actually are. Maybe the product promises results that you know are completely bogus. Or, maybe the product is created using child labor or harmful in other ways – or even potentially deadly when used wrong. So the question becomes, where is your line? What level of misrepresentation would you refuse to participate in? What lies won’t you tell to sell an idea or a product?

In short, design matters because designers know a great deal about the tools of communication. Design can manipulate minds and be persuasive in ways both good and bad. The work of a designer can make you want to exercise or smoke cigarettes.

Nowadays, this is perhaps more problematic than it has ever been. In the 1960s, Glaser made his career by being a counterculture troublemaker. But now, politics and corporations and media have become so intertwined that being a troublemaker will likely result in the kind of trouble that will simply hurt your career, not help it.

Nevertheless, designers have the knowledge and the tools to help. They know how to communicate in ways the average person doesn’t. And the conclusion Glaser comes to is that they should be good citizens and use those tools to publish, react to what’s happening, create manifestos, post their work on the streets, reach the public, and change hearts and minds for the better.

Interestingly enough, Glaser’s thoughts are echoed by another legend in the field of graphic design, Steven Heller, who spent 30 years as an art director for the New York Times. Millman has conducted 14 different interviews with Heller over the years. One of the key moments from those many interviews is when Heller explained his personal philosophy of design, and why he didn’t pursue a career in advertising or branding. For Heller, design should always serve a social purpose.

The legends of design talk about the importance of persistence and continuing to learn.

So, now that we’ve broadened our idea of design and got a sense of how important and influential it can be, let’s shift gears and look at what makes some of today’s brightest creative minds tick.

Milton Glaser is of course one of the people Millman considers a “Legend.” But so, too, are people like the designer Paula Scher, the graphic novelist Alison Bechdel, the writers Eileen Myles, Anne Lamott, and Seth Godin, and the photographer Albert Watson.

Everyone has their own story, a unique journey that led them to find a uniquely powerful and creative voice. Often, though, these journeys don’t follow a straight path. They’re not the traditional “go to college, get a job, become a success” stories. Instead, they involve chaotic upbringings, overcoming fear, taking big risky chances, and a bit of luck – the kind of luck that you create by being persistent and putting yourself in the right place at the right time.

Consider the writer Seth Godin. Today he’s a best-selling author and one of the most influential entrepreneurs in America. Like many of us, when he was in his twenties, he was going through periods of unemployment and uncertainty about where his next paycheck would come from. In Godin’s estimation, at one point early in his career he was two weeks away from bankruptcy and looking at a pile of 900 rejection letters.

What kept Godin going? As he puts it, after he left the house, he continued to raise himself “in a culture and an environment of generous persistence.” Think about that for a second. Generous persistence. What Godin is able to do is to separate his ideas from himself. If someone rejects his idea, he doesn’t feel like they’re personally rejecting him. He’s also able to look at whatever he’s trying to sell as something that’s worth more than what it costs. This way, he’s never asking someone for a favor and being rejected, he’s doing them a favor by making the offer.

Fear is the thing that often gets in the way of us doing the thing we love. As Godin sees it, we need to get a bit closer to our fear, ideally at a younger age. Learn to recognize it when it pops up, acknowledge it, realize that it isn’t something that’s going to disappear one day, and learn to dance with it rather than try to hide from it. That’s right: learn to dance with your fear. Sounds nice, doesn’t it?

Some of the Legends also mentioned time – the time it takes to find your voice and your craft, and how you never stop learning, as long as you still have time ahead of you. Photographer Albert Watson came to fame in the 1970s, when he was in his thirties, thanks to some iconic photos for magazines like GQ and Rolling Stone, and a particularly memorable shot of Alfred Hitchcock holding a dead goose by its neck for the Christmas edition of Harper’s Bazaar. Watson says it took him around 14 years of constant effort before he felt like he’d mastered his craft enough that he could have an idea and see it through in a way that felt right. Even now, as he approaches his 80th birthday, Watson is always eager to try new things and continue learning.

Some artists are hard at work trying to speak truth to power and make positive social change.

Let’s move on to the second group of interview subjects: the “Truth Tellers.” This group includes such luminaries as authors Carmen Maria Machado, Tim Ferriss, and Brené Brown, journalist Anand Giridharadas, illustrator Edel Rodriguez, and graphic novelists Chris Ware and Lynda Barry.

If we wanted to pick up that thread about design serving a social purpose, there’s perhaps no better example than illustrator Edel Rodriguez. Rodriguez came to America from Cuba as a nine-year-old boy in April 1980. He was one of 120,000 Cubans who fled Cuba around that time when the port of Mariel was briefly opened by Fidel Castro following a period of intense protests in Havana.

Rodriguez didn’t speak any English, but he could draw, and he kept drawing, even using his sketches to help communicate with other school kids in Florida. Eventually, Rodriquez left Florida to attend art school in New York, worked for MTV and Penguin Books, and became an art director for Time magazine.

Even if you don’t know his name, you’ve likely seen his illustrations. His art has graced the cover of many magazines, including an illustration for Newsweek, entitled “What Silicon Valley Thinks of Women,” which won him a National Magazine Award. But more recently his covers for Time and Der Spiegel magazine, featuring stylized depictions of Donald Trump, have sparked both accolades and controversy. In particular, there’s the infamous illustration of Trump having beheaded the Statue of Liberty.

For that image, Rodriguez was inspired by Trump’s efforts to ban Muslims from entering the US, even ones who were just trying to return to their families. Rodriguez wondered, what had happened to the country that had welcomed him and the thousands of other Cubans seeking refuge back in 1980?

Similarly, for the graphic novelist Chris Ware, empathy is everything. If you feel empathy for a group of people or a foreign country, you’re less likely to attack them. The more you try to understand what others are feeling, the less likely you are to be combative toward them. Ware sees empathy as central to humanity, but in his work, he extends his empathy toward everything. In his book Building Stories, even the apartment building where the story takes place is a character, and one that readers will come away feeling sympathy for.

Like Milton Glaser, Steven Heller, and Edel Rodriguez, Chris Ware’s work is, in his own way, tied to a social purpose. As Ware puts it, he simply tries to reflect the feeling of life as he’s experienced it. His empathy and love for his characters is part of a process of trying to understand how people turn out the way they do, and what happens when we try, in our own way, to be good people.

Creativity can benefit from structure and limitations.

In this chapter, we’ll drop in on some of the conversations in the “Culture Makers” section. This collection includes talks with the musicians Nico Muhly and Erin McKeown, the filmmaker Mike Mills, the designers Michael Bierut and Cey Adams, the authors Malcolm Gladwell and Alain de Botton, and the painter Amy Sherald.

Debbie Millman is kind of fascinated by music. For her, creating a musical work is a mysterious process, like making something out of nothing. This comes up in most of her talks with musicians. How do you do it? How do you sit down and pull a song out of the ether?

Nico Muhly makes all kinds of music – chamber pieces, orchestral works, as well as music for operas, ballets, and films. One of Muhly’s inspirations is church music. Church music doesn’t really draw attention to itself. It’s not self-referential. When a piece of music played in a church is over, the performer doesn’t take a bow, the audience doesn’t applaud. Both the composer and the performer essentially disappear. Muhly likes this idea. He wants his music to fit perfectly within and complement an environment, not stand out.

At the same time, he likes to work within a structure that allows him to be adventurous. As he puts it, when you hang your art on a familiar and solid structure, you then have more room to be “weird and stylized.” To help explain, he makes a food analogy. Some people like to follow a strict recipe. They chop and measure out 100 different ingredients ahead of time and follow each and every step to achieve an ambitiously impressive and delicious result. There’s nothing wrong with that approach, but Muhly also likes to buy six ingredients that look good, bring them home, and figure out what exciting new thing you can create with them.

In a way, designer Michael Bierut echoes some of these ideas. As a partner of the design firm Pentagram, Bierut’s been at the forefront of modern design, working for clients as diverse as Harley-Davidson and Atlantic magazine. From his perspective, one of the worst assignments you can get is “do whatever you want.” He needs parameters, limitations. In other words, he’d rather be forced to work with a few ingredients than a hundred. If there isn’t a fun challenge involved, he’ll turn the project down.

Bierut even offers a musical analogy to describe his philosophy. He really admires the Motown songwriting team of Lamont Dozier, Eddie Holland, and Brian Holland. On the nights and weekends, this trio would play freewheeling jazz music at nightclubs. During the day, they were salaried songwriters, cranking out tunes for Motown Records. They were doing what you might call “hack” work. Maybe it wasn’t as experimental and creative as they wanted to be – they had to work within the parameters of the Motown brand. But eventually, they created a remarkable string of top-ten hits, like “Dancing in the Streets,” “Stop In the Name of Love,” and “You Keep Me Hanging On.” These are all songs that continue to enchant listeners decades later and inspire people like Bierut.

Also like Nico Muhly, the designer Cey Adams doesn’t make work in order to stand under a spotlight and take a bow. He was the founding art director of Def Jam Recordings, creating iconic album covers for Public Enemy and the Beastie Boys, before continuing his career with companies like Nike and HBO. From the start, he’s defined a successful work as something that helps the musicians or the product shine bright. It’s not about him, it’s all about the job, and being able to happily move on to the next one.

You can overcome problems by doing the work and asking the right questions.

We’ve reached chapter number five, which means it’s time to dive into the category of “Trendsetters.” Yet again, this is an eclectic group of artists that includes the musician Amanda Palmer, the designers Chip Kidd and Emily Oberman, the photojournalist Brandon Stanton, the playwright Michael R. Jackson, and the chef Christina Tosi.

The word trendsetter implies doing something new, going out on a limb, taking a chance, being different. The opposite of playing it safe. So, yeah, following your muse and using your voice, sometimes it can be scary. Back in the second chapter, we talked a bit about that four-letter word “fear,” and teaching yourself how to dance with it rather than hide away from it. This is something that photojournalist Brandon Stanton had to learn how to do – and do it on the job, no less.

Stanton is the man behind the Humans of New York website and subsequent books. Basically, Stanton finds someone on the streets, talks to them, takes their picture, and tells their story to his audience. It started out in New York, but it’s since moved on to other cities and other countries, including Pakistan. Purposefully, Stanton has sought out neighborhoods with bad reputations to show that people no different from you and me live in these places. This guy? The guy with tattoos completely covering his face? He’s also got a rich inner life, a broken heart, and hopes and dreams for the future.

Walking up to strangers on the street isn’t something that came easily to Stanton. In fact, the thought terrified him. But like anything else, overcoming this fear – or learning to dance with it, if you will – proved to be a learned skill. Something that you can master simply by doing it, gaining positive experience, and eventually gaining a level of comfort.

Stanton taught himself photography in a similar way. At first, he simply approached it from a practical perspective. He’d take 20 photos of his subjects from 20 different angles. He figured, at least a couple of them would later prove to be useful. Over time, from looking at the results and picking his favorites, he started to recognize a personal aesthetic preference. So then it became 15 different angles. Then ten. Then five. It didn’t happen overnight, but he eventually mastered his fear and his craft, making striking portraits and sharing powerful stories.

But what is a story? How do you know a good one when you have it? Playwright Michael R. Jackson finds it helpful to boil it down to its essence. Jackson’s playwriting and screenwriting teacher taught him a helpful shorthand: A story is a character who wants something. They are given obstacles, and they either achieve, abandon, or fail to get what they want. So, when writer’s block begins to set in, Jackson steps back and asks, what do they want? How are they going about trying to get it? Will they win? Will they lose? Or will the character change and no longer have that initial desire? Not a bad tip, right?

Creativity can come from a mix of confidence, doubt, and staying true to your beliefs.

Here we are, at the sixth and final chapter – the one where we look at some of the big names – the “Visionaries.” People like musician David Byrne, artists Marina Ambramović and Shepard Fairey, illustrator Maira Kalman, radio and podcast producer Ira Glass, and internet cultural curator Maria Popova. All of these folks have, in one way or another, changed the game. Byrne, and his bandmates in Talking Heads, changed rock and roll. Ambramović changed modern art by pushing the boundaries of performance art.

Shepard Fairey is also testing boundaries, albeit in a different way. In the 1980s, Fairey was into skateboarding and punk rock. But he always had an interest in art and when he began taking classes in graphic design and screen printing, it was like he’d found his true calling. This led to Fairey making the streets his gallery of choice, putting up handmade stickers and posters.

For Fairey, street art appealed to his punk rock DIY ethics. But he also admits that he wasn’t exactly confident enough to send out samples of his work or take meetings, nor did he want to pander to the elitist folks within the fine art world. In fact, even though he’s now one of the most high-profile names in the art world, that’s something that he’s still not comfortable doing. This has caused some controversy since Fairey insists on keeping his work affordable for those he still cares about: skateboarders, punk rockers, college kids. So, on top of doing work for brands like Coca-Cola and Dewar’s Scotch, he still makes money selling T-shirts and $35 screen prints. Some might call him a sellout, others might call him a rebel who continues to play by his own rules.

Fairey sees it as a delicate balance – deciding on whether to take a project based on its own merits. It’s not unlike consulting with Mitch Glaser’s 12 steps. He’s taken some Coca-Cola gigs and rejected others. It depends. What matters is that he has to be able to stand behind the idea, 100 percent.

That doesn’t mean you can’t have doubts. Designer Maira Kalman has written and illustrated dozens of wildly celebrated books, including The Pursuit of Happiness and The Principles of Uncertainty. But she still considers doubting and fretting as part of the everyday process. As she puts it, “I think what I do is terrible. I’m constantly tormented.” But for Kalman, it’s the duality of the artist – being both incredibly insecure and fiercely driven. This is where her creativity comes from: it generates a sort of frantic excitement that produces great work.

Kalman, like other artists we’ve covered, also likes a good assignment. She doesn’t have the sort of creative mind that can just walk into the studio and, again, pull a fantastic idea out of the ether. This is why Kalman enjoyed working for publications like the New Yorker and the New York Times. She could look at her work as journalism – looking at the world, observing, and sending an illustrated report back to the office.

In a way, it’s just like composer Nico Muhly said – having a recognizable structure on which to hang your ambitious and stylized art. Perhaps it makes sense, then, that Kalman and Muhly collaborated on an opera entitled The Elements of Style.

Hopefully, these snippets from Millman’s conversations will give you some ideas about how to develop your own style, your own sense of design and creativity. Maybe the ideas here will help you find your voice and dance with your fear.

About the author

Debbie Millman is a designer, curator, artist, and writer. She was the art director of Print magazine, and a partner and president of the Design Division at Sterling Brands, where she worked on a number of high-profile campaigns for such clients as Pepsi and Nestlé. Since 2005, she’s been hosting and interviewing creative people for her Design Matters podcast.

Named “one of the most influential designers working today” by Graphic Design USA, Debbie Millman is also an author, educator, brand strategist and host of the podcast Design Matters. Debbie is Chief Marketing Officer at Sterling Brands, where she has worked with over 200 of the world’s largest brands. As the founder and host of Design Matters, the first and longest running podcast about design, Millman has interviewed more than 250 design luminaries and cultural commentators, including Massimo Vignelli, Milton Glaser, Malcolm Gladwell, Dan Pink, Barbara Kruger, Seth Godin and more. In the ten years since its inception, the show has garnered millions of downloads and a Cooper Hewitt National Design Award.

Debbie is the author of six books, including two collections of interviews that have extended the ethos and editorial vision of Design Matters to the printed page: How to Think Like a Great Graphic Designer and Brand Thinking and Other Noble Pursuits. Both books have been published in over 10 languages. In 2009 Debbie co-founded with Steven Heller the world’s first graduate program in branding at the School of Visual Arts in New York City. Now in its sixth year, the program has achieved international acclaim. The inaugural class wrote and designed the Rockport book Brand Bible: The Complete Guide to Building, Designing and Sustaining Brands, in 2013 the students created branding for the Museum of Modern Art’s retail program, Destination: New York and the class of 2015 worked to reposition a Kappa Middle School in Harlem.

Debbie’s written and visual essays have appeared in publications such as The New York Times, New York Magazine, Print Magazine, Design Observer and Fast Company. She is the author of two books of illustrated essays: Look Both Ways and Self-Portrait As Your Traitor; the later of which has been awarded a Gold Mobius, a Print Typography Award, and a Bronze Medal from the Art Directors Club. Her artwork has been exhibited at the Chicago Design Museum, Anderson University, School of Visual Arts, Long Island University and The Wolfsonion Museum. She has been artist-in-residence at Cranbrook University, Old Dominion University and Notre Dame University, and has conducted visual storytelling workshops at Academy of Art University in San Francisco, the University of Utah, Hartford University and the High School of Art and Design in New York. She has designed wrapping paper and beach towels for One Kings Lane, greeting cards for Mohawk, MOO and Card-To-Art, playing cards for DeckStarter and sketchbooks for Shutterstock.

Debbie is President Emeritus of AIGA, one of five women to hold the position in the organization’s 100-year history. She is also a past board member and treasurer of the New York Chapter. She is a frequent speaker on design and branding and has moderated Design Yatra in India, presented keynote lectures at Rotman School of Management, Princeton University, Michigan Modern, the Melbourne Writers Festival in Australia, Design Thinkers in Toronto, the American Package Design Summit, the Festival of Art and Design in Barcelona, and many more. She has been a juror for competitions including Cannes Lions, The Art Directors Club, The Type Directors Club, Fast Company, HOW Magazine, Print Magazine, ID Magazine, AIGA, The Dieline, and more.


Arts, Photography, Graphic Design, Business of Art Reference, Commercial Graphic Design, Creativity, Art Finance, Graphic Design, Management, Leadership, Motivation, Personal Development, Advice On Careers & Achieving Success, Popular Psychology, Assertiveness, Motivation & Self-esteem, Memory Improvement & Thinking Techniques


Foreword by Roxane Gay

“Debbie Millman brings her Design Matters podcast, ‘about how the most creative people in the world create their lives,’ to the page with this excellent interview anthology. Sharpened by Millman’s penetrating commentary, the candid musings teem with insight and empathy. This sparkling collection is one to be savored slowly.”—Publisher’s Weekly

The author, educator, brand consultant, and host of the widely successful and award-winning podcast Design Matters showcases dozens of her most exciting interviews, bringing together insights and reflections from today’s leading creative minds from across diverse fields.

“Debbie Millman has become a singular voice in the world of intimate, enlightening conversations. She has demonstrated time, and again, why design matters.”—Roxane Gay, from the foreword

Over the course of her popular podcast’s fifteen-year reign, Debbie Millman has interviewed more than 400 creative minds. In those conversations, she has not only explored what it means to design a creative life, but has, as Millman’s wife, Roxane Gay, assesses in her foreword, “created a gloriously interesting and ongoing conversation about what it means to live well, overcome trauma, face rejection, learn to love and be loved, and thrive both personally and professional.”

In this illustrated, curated anthology, Millman includes approximately 80 of her best interviews with visionaries from across diverse fields. Grouped by category—Legends, Truth Tellers, Culture Makers, Trendsetters, and Visionaries—these eye-opening, entertaining, and enlightening conversations—offer insights into new ways of being and living.

Accompanying each entry is a brief biography, a portrait photographed by Millman, and a pull quote written in Millman’s artistic hand. Why Design Matters features 100 images and includes interviews with:

Marina Abramovic, Cey Adams, Elizabeth Alexander, Laurie Anderson, Lynda Barry, Allison Bechdel, Michael Bierut, Brené Brown, Alain de Botton, Eve Ensler, Shepard Fairey, Tim Ferriss, Louise Fili, Kenny Fries, Anand Girhidardas, Cindy Gallop, Malcolm Gladwell, Milton Glaser, Ira Glass, Seth Godin, Thelma Golden, Gabrielle Hamilton, Steven Heller, Jessica Hische, Michael R. Jackson, Oliver Jeffers, Saeed Jones, Thomas Kail, Maira Kalman, Chip Kidd, Anne Lamott, Elle Luna, Carmen Maria Machado, Thomas Page McBee, Erin McKeown, Chanel Miller, Mike Mills, Marilyn Minter, Isaac Mizrahi, Nico Muhly, Eileen Myles, Emily Oberman, Amanda Palmer, Priya Parker, Esther Perel, Maria Popova, Edel Rodriguez, Paula Scher, Amy Sherald, Simon Sinek, Pete Souza, Aminatou Sow, Brandon Stanton, Cheryl Strayed, Amber Tamblyn, Christina Tosi, Tea Uglow, Chris Ware, and Albert Watson.


Debbie Millman brings her Design Matters podcast, ‘about how the most creative people in the world create their lives,’ to the page with this excellent interview anthology. Sharpened by Millman’s penetrating commentary, the candid musings teem with insight and empathy. This sparkling collection is one to be savored slowly. – Publishers Weekly

Why Design Matters: Conversations With the World’s Most Creative People by Debbie Millman is a curated anthology by the Design Matters award-winning podcast host and branding visionary. This salon in book form features text from Millman’s conversations with the world’s most creative minds, thought leaders, and intellectuals, each with an introduction from Millman. It’s a visually stunning, often revealing, and always enlightening work that readers will turn to repeatedly for inspiration.

Design Matters With Debbie Millman is one of the world’s very first podcasts and the first ever about design and an inquiry into the broader world of creative culture. Broadcasting independently for 17 years, the show is about how incredibly creative people design the arc of their lives.

“Love, Life, and the Pursuit of Creative Space” Unlocking Us podcast episode, with Roxane Gay and Debbie Millman

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