Introduction
Draw inspiration from the words and insights of America’s leading creative minds.
Since 2005, Debbie Millman has been regularly interviewing some of the most brilliant figures in the creative world to discuss their lives and work. While many guests have been influential in graphic design, today Millman is just as likely to interview writers or Broadway directors as she is illustrators or graphic artists. As you’ll soon discover, design is everywhere – on the page, stage, screen, in the clothes you wear, and the packaging of your food. Ultimately, design is about communicating ideas; it’s the essence of art, creativity, and life.
If you’re a subscriber to Debbie Millman’s interview podcast *Design Matters*, you’ll know how enjoyable it is to hear the insights of designers, illustrators, directors, songwriters, photographers, and other creatives. While we’ll explore many of the insights shared by Millman’s guests here, this book is an adaptation of a book that originated from a podcast. So, while we can’t capture the experience of listening to the guests directly, we can highlight the key ideas that make these individuals such exceptional creatives. To do so, we focused on two core questions while creating this book: What common themes do creative minds share? And, of course, why does design matter?
In this book, you’ll discover:
– how constraints can fuel creativity,
– that drawing serves as a universal language, and
– why embracing your fears is essential for growth.
Key idea 1
Design is important because it serves as a powerful means of communication.
If you’re familiar with the history of graphic design, you’ve likely heard the name Milton Glaser.
Milton Glaser is truly a legend in the design world, known for cofounding New York magazine and creating some of the most iconic images of the 1960s and 1970s, such as the famous “I Love New York” logo. His name has become synonymous with design. What further solidifies his legendary status is the thoughtful reflection he’s devoted to why design is important. He even authored a well-known article titled “12 Steps on the Designer’s Road to Hell.”
In his article, Glaser outlines many difficult decisions that designers face throughout their careers, each representing a step either toward or away from “hell.” Why such strong language? It boils down to the fact that designers communicate with the public. From milk cartons to presidential campaigns, every design is the result of someone’s deliberate choices. And, as we know, some designs are meant to mislead—whether by making a product appear larger, healthier, or more effective than it really is. It could involve endorsing a product made with unethical practices like child labor, or one that’s harmful or even dangerous when misused. So the key question is: where do you draw the line? What level of misrepresentation would you refuse to engage in? What lies are you unwilling to tell to promote an idea or product?
In essence, design matters because designers are skilled in the art of communication. Design has the power to influence and persuade, for better or worse. A designer’s work can motivate you to exercise or encourage you to smoke.
Today, this influence is more complicated than ever. In the 1960s, Glaser built his career as a counterculture disruptor, but now, with politics, corporations, and media so deeply interconnected, being a rebel is more likely to harm your career than help it.
Despite these challenges, designers possess the expertise and tools to make a positive impact. They understand how to communicate in ways that go beyond the average person’s abilities. Glaser’s conclusion is that designers should act as responsible citizens, using their skills to publish, respond to current events, create manifestos, display their work publicly, engage with people, and influence hearts and minds for the better.
Interestingly, Glaser’s views are shared by another graphic design legend, Steven Heller, who worked as an art director at The New York Times for 30 years. Over the years, Millman has interviewed Heller 14 times. One of the standout moments from these conversations was when Heller shared his personal design philosophy, explaining why he chose not to pursue a career in advertising or branding. For Heller, design should always have a social purpose.
Key idea 2
The legends of design emphasize the value of persistence and lifelong learning.
Now that we’ve expanded our understanding of design and recognized its significant influence, let’s shift focus to what drives some of today’s most brilliant creative minds. In addition to Milton Glaser, who Millman considers a “Legend,” others in this category include designer Paula Scher, graphic novelist Alison Bechdel, writers Eileen Myles, Anne Lamott, and Seth Godin, as well as photographer Albert Watson.
Each person has their own story, a unique path that helped them discover their distinct and powerful creative voice. However, these journeys rarely follow a straight line. They aren’t the typical “go to college, land a job, and find success” narratives. Instead, they often include turbulent beginnings, conquering fears, taking bold risks, and relying on a bit of luck—the kind of luck that comes from persistence and being in the right place at the right time.
Take the writer Seth Godin, for example. He’s now a best-selling author and one of America’s most influential entrepreneurs. However, like many of us, he faced periods of unemployment and uncertainty in his twenties, unsure where his next paycheck would come from. By Godin’s account, early in his career, he was just two weeks away from bankruptcy and had accumulated a stack of 900 rejection letters.
What motivated Godin to keep going? He explains that after leaving his house, he immersed himself “in a culture and an environment of generous persistence.” Take a moment to reflect on that phrase: generous persistence. Godin manages to distinguish his ideas from his personal identity; when someone rejects his idea, he doesn’t take it as a personal rejection. Additionally, he views whatever he is trying to sell as having greater value than its cost. As a result, he doesn’t see himself as asking for a favor and facing rejection; instead, he feels he is doing others a favor by presenting them with an offer.
Fear is often what prevents us from pursuing the things we love. According to Godin, we should confront our fears earlier in life. We need to learn to recognize fear when it arises, acknowledge it, understand that it won’t just go away someday, and find a way to coexist with it rather than avoid it. In other words, we should learn to dance with our fear. It sounds appealing, doesn’t it?
Several of the Legends also emphasized the importance of time—the time it takes to discover your voice and hone your craft, and the idea that learning never truly ends as long as you have time ahead of you. Photographer Albert Watson gained recognition in the 1970s, during his thirties, through iconic images for magazines like GQ and Rolling Stone, including a memorable photo of Alfred Hitchcock holding a dead goose by the neck for the Christmas issue of Harper’s Bazaar. Watson explains that it took him about 14 years of relentless effort before he felt he had mastered his craft to the point where he could generate an idea and execute it in a way that felt authentic. Even now, as he nears his 80th birthday, Watson remains enthusiastic about trying new things and continuing his learning journey.
Key idea 3
Some artists are dedicated to speaking truth to power and driving positive social change.
Now, let’s turn our attention to the second group of interview subjects: the “Truth Tellers.” This group features prominent figures such as authors Carmen Maria Machado, Tim Ferriss, and Brené Brown; journalist Anand Giridharadas; illustrator Edel Rodriguez; and graphic novelists Chris Ware and Lynda Barry.
To continue the discussion about design’s role in serving a social purpose, illustrator Edel Rodriguez is a particularly notable example. Rodriguez immigrated to the United States from Cuba at the age of nine in April 1980. He was among 120,000 Cubans who left Cuba during that period when Fidel Castro temporarily opened the port of Mariel in response to significant protests in Havana.
Rodriguez didn’t know any English, but he could draw, and he continued to sketch, even using his drawings to communicate with other kids at school in Florida. Eventually, he left Florida to attend art school in New York, where he worked for MTV and Penguin Books before becoming an art director for Time magazine.
Even if you aren’t familiar with his name, you’ve probably encountered his illustrations. His artwork has appeared on the covers of numerous magazines, including a piece for Newsweek titled “What Silicon Valley Thinks of Women,” which earned him a National Magazine Award. More recently, his covers for *Time* and Der Spiegel, which feature stylized portrayals of Donald Trump, have generated both praise and controversy. Notably, there is the infamous illustration depicting Trump beheading the Statue of Liberty.
For that illustration, Rodriguez drew inspiration from Trump’s attempts to prevent Muslims from entering the U.S., including those simply trying to reunite with their families. He reflected on what had happened to the nation that had welcomed him and thousands of other Cubans seeking refuge in 1980.
Likewise, for graphic novelist Chris Ware, empathy is essential. When you empathize with a group of people or a foreign country, you are less inclined to attack them. The more you strive to understand others’ feelings, the less likely you are to respond with hostility. Ware believes that empathy is fundamental to being human, and in his work, he broadens his empathy to encompass everything. In his book *Building Stories*, even the apartment building where the narrative unfolds is portrayed as a character, one that readers will feel sympathy for.
Similar to Milton Glaser, Steven Heller, and Edel Rodriguez, Chris Ware’s work is connected to a social purpose in his own unique way. According to Ware, he aims to reflect the experience of life as he has lived it. His empathy and affection for his characters are part of his effort to understand how people become who they are and what occurs when we strive, in our own ways, to be good individuals.
Key idea 4
Creativity can thrive within the framework of structure and limitations.
In this important discussion, we’ll explore some of the conversations from the “Culture Makers” section. This collection features discussions with musicians Nico Muhly and Erin McKeown, filmmaker Mike Mills, designers Michael Bierut and Cey Adams, authors Malcolm Gladwell and Alain de Botton, and painter Amy Sherald.
Debbie Millman has a deep fascination with music. She views the process of creating a musical piece as a mysterious endeavor, akin to conjuring something from nothing. This topic often arises in her discussions with musicians. How is it done? How do you sit down and extract a song from thin air?
Nico Muhly composes a diverse range of music, including chamber works, orchestral pieces, and compositions for operas, ballets, and films. One significant influence on Muhly is church music, which tends to be understated and does not seek the spotlight. In a church setting, there are no bows or applause at the end of a performance; both the composer and the performer fade into the background. Muhly appreciates this concept and aims for his music to seamlessly integrate with its surroundings rather than draw attention to itself.
Muhly enjoys working within a framework that gives him the freedom to be experimental. He believes that when you base your art on a familiar and sturdy structure, it allows for more “weird and stylized” creativity. To illustrate this point, he uses a food analogy: some people prefer to adhere strictly to a recipe, meticulously preparing and measuring out numerous ingredients to create an impressive dish. While he acknowledges the validity of this method, Muhly also appreciates the spontaneity of choosing just six appealing ingredients, taking them home, and discovering what exciting new dish he can make with them.
Designer Michael Bierut reflects similar sentiments. As a partner at the design firm Pentagram, he has been a leading figure in modern design, collaborating with a wide range of clients, including Harley-Davidson and Atlantic magazine. From his viewpoint, one of the least desirable tasks is to simply “do whatever you want.” He prefers to have clear parameters and limitations; in other words, he’d rather work with a handful of elements than an overwhelming number. If a project doesn’t present an enjoyable challenge, he is likely to decline it.
Bierut uses a musical analogy to illustrate his philosophy, expressing admiration for the Motown songwriting team of Lamont Dozier, Eddie Holland, and Brian Holland. In their free time, this trio would perform improvisational jazz at nightclubs, while during the day, they worked as salaried songwriters producing songs for Motown Records. Although this could be seen as “hack” work and may not have been as experimental or creative as they wished, as they had to operate within the constraints of the Motown brand, they ultimately crafted an impressive series of top-ten hits, including “Dancing in the Streets,” “Stop In the Name of Love,” and “You Keep Me Hanging On.” These songs continue to captivate audiences even decades later and inspire figures like Bierut.
Similar to Nico Muhly, designer Cey Adams doesn’t create art to seek attention or take a bow. As the founding art director of Def Jam Recordings, he designed memorable album covers for artists like Public Enemy and the Beastie Boys, and he later worked with companies such as Nike and HBO. From the beginning, he has viewed successful work as that which allows the musicians or products to take center stage. For him, it’s not about personal recognition; it’s about the work itself and the satisfaction of moving on to the next project.
Key idea 5
You can solve challenges by putting in the effort and posing the right questions.
We’ve arrived at key point number five, signaling the start of the “Trendsetters” category. This diverse group of artists features musician Amanda Palmer, designers Chip Kidd and Emily Oberman, photojournalist Brandon Stanton, playwright Michael R. Jackson, and chef Christina Tosi.
The term “trendsetter” suggests embracing the new, taking risks, and standing out—essentially, it’s about avoiding the safe route. Following your muse and expressing your voice can indeed be intimidating. In the second key idea, we discussed the four-letter word “fear” and the importance of learning to navigate it rather than retreating from it. This is a lesson that photojournalist Brandon Stanton had to learn, and he did so while actively working in the field.
Brandon Stanton is the creator of the Humans of New York website and its subsequent books. He approaches people on the streets, engages them in conversation, takes their photographs, and shares their stories with his audience. While it began in New York, the project has expanded to other cities and countries, including Pakistan. Stanton intentionally explores neighborhoods with negative reputations to highlight that ordinary people, just like you and me, reside in these areas. For example, the man with tattoos covering his entire face also has a deep inner life, a broken heart, and aspirations for the future.
Approaching strangers on the street was not an easy task for Stanton; in fact, it terrified him. However, much like any other challenge, conquering this fear—or learning to navigate it—became a skill he developed over time. It’s something that can be mastered through practice, accumulating positive experiences, and gradually building a sense of comfort.
Stanton learned photography in a similar manner. Initially, he approached it practically by taking 20 photos of his subjects from various angles, believing that a few of those would be useful later on. As he reviewed the results and selected his favorites, he began to develop a personal aesthetic. Gradually, he reduced the number of angles he shot from—first to 15, then to 10, and finally to five. This didn’t happen instantly, but he ultimately overcame his fear and honed his craft, creating striking portraits and sharing impactful stories.
But what exactly is a story, and how can you identify a good one? Playwright Michael R. Jackson finds it useful to distill it to its core elements. A teacher of his in playwriting and screenwriting provided a helpful framework: a story consists of a character with a desire who faces obstacles and either achieves, abandons, or fails to attain their goal. When writer’s block strikes, Jackson takes a step back to consider what the character wants, how they’re trying to achieve it, and whether they will succeed, fail, or undergo a change that alters their initial desire. That’s a valuable tip, isn’t it?
Key idea 6
Creativity often stems from a blend of confidence, doubt, and staying true to one’s principles.
Now, we arrive at the sixth and final key idea, where we examine some prominent figures known as the “Visionaries.” This group includes musician David Byrne, artists Marina Abramović and Shepard Fairey, illustrator Maira Kalman, radio and podcast producer Ira Glass, and internet cultural curator Maria Popova. Each of these individuals has made a significant impact in their respective fields. For instance, Byrne and his fellow band members in Talking Heads transformed rock and roll, while Abramović reshaped modern art by challenging the limits of performance art.
Shepard Fairey is also pushing boundaries, though in a different manner. In the 1980s, he was involved in skateboarding and punk rock, but he always had a passion for art. When he started taking classes in graphic design and screen printing, he discovered his true calling. This revelation inspired Fairey to turn the streets into his preferred gallery, where he showcased his work by putting up handmade stickers and posters.
For Fairey, street art resonated with his punk rock DIY values. However, he acknowledges that he lacked the confidence to send out samples of his work or attend meetings, and he didn’t want to cater to the elitist circles of the fine art world. Even though he is now a prominent figure in the art community, he still feels uncomfortable with that aspect of the industry. This has led to some controversy, as Fairey insists on keeping his work affordable for those he cares about, such as skateboarders, punk rockers, and college students. As a result, in addition to his projects for brands like Coca-Cola and Dewar’s Scotch, he continues to earn income by selling T-shirts and $35 screen prints. While some might label him a sellout, others view him as a rebel who adheres to his own principles.
Fairey views it as a careful balancing act when deciding whether to accept a project based on its individual merits. This approach is somewhat similar to Mitch Glaser’s 12 steps. He has accepted some projects for Coca-Cola while turning down others, depending on the circumstances. Ultimately, what’s crucial for him is that he can fully support the idea, 100 percent.
Having doubts doesn’t mean you can’t succeed. Designer Maira Kalman has authored and illustrated numerous highly acclaimed books, such as The Pursuit of Happiness and The Principles of Uncertainty. Despite her success, she views doubt and anxiety as an integral part of her daily routine. As she expresses, “I think what I do is terrible. I’m constantly tormented.” For Kalman, this reflects the dual nature of being an artist—feeling both deeply insecure and passionately driven. This inner conflict fuels her creativity, creating a sense of frantic excitement that leads to outstanding work.
Like the other artists we’ve discussed, Kalman appreciates a solid assignment. She doesn’t possess the type of creative mindset that allows her to simply walk into the studio and conjure up a brilliant idea out of thin air. This is why she found working for publications such as The New Yorker and The New York Times enjoyable. She viewed her work as a form of journalism—observing the world around her and sending back illustrated reports to her editors.
In a sense, it aligns with what composer Nico Muhly mentioned about having a familiar structure to support your ambitious and stylized art. It’s fitting, then, that Kalman and Muhly teamed up to create an opera titled The Elements of Style.
Hopefully, these excerpts from Millman’s discussions will inspire you to cultivate your own style and enhance your sense of design and creativity. Perhaps the concepts presented here will assist you in discovering your voice and embracing your fears.
