Why Design Matters

Why Design Matters Plot Summary

Introduction

The sun was setting as I sat across from a renowned artist in her studio. Paint-splattered hands gestured wildly as she described her creative process, not as a series of calculated decisions, but as a continuous dialogue with her materials, her surroundings, and her inner voice. "The most important thing," she said, leaning forward, "is asking the right questions. Not to find immediate answers, but to open doors you didn't know existed." That conversation changed how I approached creativity forever. Creative minds don't simply produce work—they engage in transformative conversations with the world. Through intimate dialogues with visionaries across disciplines, we discover that creativity isn't merely about talent or technique, but about the courage to question, the willingness to listen, and the vulnerability to share. These conversations reveal how creative individuals navigate self-doubt, find their authentic voice, and transform personal struggles into meaningful expression. By witnessing their journeys, we learn that creativity isn't a mysterious gift bestowed upon a select few, but a practice of presence, persistence, and profound human connection that we all can cultivate.

Chapter 1: The Spark: Moments That Ignite Creative Paths

The morning sun filtered through the studio windows as Milton Glaser sketched the initial lines of what would become one of the most recognizable logos in history. With just a few strokes, "I ♥ NY" began to take shape—simple, direct, and destined to transcend mere marketing to become a cultural touchstone. When asked years later about this moment of creation, Glaser shrugged with characteristic humility. "I did the sketch in the back of a taxi," he said, downplaying the flash of genius that would help revitalize an entire city's image. This moment exemplifies what makes legendary creators different—not just their output, but their approach to the creative process itself. The true legends of design, art, and creative thinking understand that their work exists in service to something greater than themselves. As Glaser himself articulated in his "12 Steps on the Designer's Road to Hell," creators face moral choices with every project they undertake. From designing packages that appear larger on shelves (a minor deception) to creating advertisements for harmful products (a major ethical breach), creative professionals navigate a complex moral landscape where technical skill must be balanced with human responsibility. The path to legendary status rarely follows a straight line. Alison Bechdel, whose graphic memoirs have redefined autobiographical storytelling, spent years creating her underground comic strip "Dykes to Watch Out For" before achieving mainstream recognition. When her father died—a closeted gay man who had maintained a carefully constructed facade—Bechdel began the painstaking work of documenting her family's complex history through words and images. The resulting memoir, "Fun Home," took seven years to complete and became a critical sensation, eventually adapted into a Tony Award-winning musical. What distinguishes creative legends is their willingness to persist through periods of rejection and doubt. Paula Scher, whose typographic innovations have shaped contemporary visual culture, faced harsh criticism early in her career. Her Swatch Watch poster design was maligned as plagiarism despite having received permission from the original artist's estate. "It was an homage," Scher explained, noting that proper credit had been given. Yet the design community's reaction revealed how even established creators face scrutiny and misunderstanding. The stories of creative legends remind us that greatness emerges not just from talent but from resilience and ethical clarity. As Anne Lamott discovered when her first book failed commercially, success requires wholehearted commitment. "If I fail wholeheartedly, I can live with that," she reflected. "If I fail and I've been half-assed or half-hearted in my effort, that I cannot live with." This philosophy—embracing full commitment regardless of outcome—characterizes those who eventually shape their fields and inspire generations that follow.

Chapter 2: Navigating Uncertainty: Finding Direction in Chaos

The university auditorium fell silent as Brené Brown paused, considering how to answer the student's question about fear. "I'm afraid if I do this and I fail, I will die of a broken heart," the young man had admitted. Brown nodded, recognizing the universal fear behind his specific words. "The only people who don't have heartbreak in their careers are people who have no love or passion for their career," she replied. "Heartbreak is, while miserable when you're in it, a small price to pay for doing work that you're profoundly in love with. I find hearts that are stretch-marked and scarred to be far more profound than clean shiny new hearts." This exchange captures the essence of truth-telling: the willingness to acknowledge vulnerability as the gateway to authentic connection. Brown, whose research on shame and vulnerability has transformed our understanding of human relationships, discovered this truth through her own painful journey. After collecting thousands of interviews about connection, she realized that the qualities she identified in "wholehearted" people were precisely the qualities she herself lacked. "I looked at the 'don't' list, and that described me to a T," she admitted. "Don't try to be cool, try to be perfect, try to derive your status from how exhausted you are and how hard you work." The paradox Brown identified lies at the heart of human connection: "When I meet you, the very first thing I look for in you is vulnerability, and the very last thing I want to show you is my vulnerability. I'm desperately seeking yours while hiding mine." This insight helps explain why truth-telling feels simultaneously terrifying and liberating—we fear rejection for our authentic selves yet crave the connection that only authenticity can provide. For writer Cheryl Strayed, truth-telling became both personal salvation and professional calling. After her mother's death sent her spiraling into self-destruction, including heroin use and the dissolution of her marriage, Strayed embarked on a 1,100-mile solo hike along the Pacific Crest Trail. This journey, later chronicled in her memoir, forced her to confront the raw truth of her grief and resilience. Years later, as the anonymous advice columnist "Dear Sugar," Strayed answered readers' questions with unflinching honesty about her own mistakes and vulnerabilities, creating a new template for how truth can heal both the teller and the listener. The power of truth-telling extends beyond personal relationships to societal structures, as demonstrated by Anand Giridharadas's critique of elite philanthropy. After years embedded in wealthy circles, Giridharadas exposed how billionaire "change-makers" often preserve the very systems that create inequality while claiming to solve social problems. "These billionaire saviors often insist on changing the world in ways that protect their own privileges," he observed. By speaking this uncomfortable truth, Giridharadas challenged powerful interests and sparked essential conversations about genuine social change.

Chapter 3: The Power of Connection: Collaboration and Growth

The small apartment in East Village hummed with creative energy as a young artist hunched over her drawing table, carefully inking panels for an underground comic strip. It was 1983, and Alison Bechdel was creating the first installment of what would become "Dykes to Watch Out For," a groundbreaking comic that would run for twenty-five years. "I wanted to see images of people like me which I didn't see anywhere in the culture at that point," Bechdel explained years later. In that moment, working in obscurity with no guarantee of success, she was doing something revolutionary: making culture that reflected lives rendered invisible by mainstream media. Culture makers like Bechdel don't merely create art—they expand our collective imagination about what's possible. By depicting lesbian characters living ordinary lives with humor and complexity, Bechdel created what she called "a parallel world where gay people were making their own art and newspapers and had their own bookstores and bars." This parallel cultural universe provided both representation for those within the community and a window for those outside it, gradually transforming the broader cultural landscape. The power to shape culture often emerges from personal necessity rather than calculated ambition. For musician David Byrne, creating the Talking Heads' distinctive sound came from embracing his limitations rather than trying to overcome them. "I couldn't do the kind of singing that was popular at the time," Byrne admitted. Instead of mimicking rock conventions, he developed his own nervous, intellectual performance style that helped define an entire musical movement. By turning perceived weaknesses into signature strengths, Byrne demonstrated how authentic expression can reshape cultural expectations rather than conforming to them. Culture makers frequently operate at the intersection of multiple traditions, creating new forms by combining elements previously kept separate. Artist Amy Sherald, whose portrait of Michelle Obama brought her international recognition, developed her distinctive style by merging classical portraiture techniques with a palette that deliberately subverts racial expectations. By painting Black subjects with gray-toned skin against vibrant backgrounds, Sherald created a visual language that comments on race while simultaneously transcending simplistic categorizations. "I paint American people, and I paint Americans who happen to be Black," she explained, refusing to be limited by others' expectations of what Black art should be. The most influential culture makers transform not just what we see but how we see. Philosopher and writer Alain de Botton founded The School of Life to address what he saw as a critical gap in modern education: guidance on how to live well. Rejecting the academic tendency to treat philosophy as an abstract intellectual exercise, de Botton created accessible content addressing everyday concerns like career frustration, relationship difficulties, and the search for meaning. By treating these universal human struggles with intellectual seriousness, he helped legitimize emotional intelligence as a cultural value worth cultivating.

Chapter 4: Breaking Through: Overcoming Creative Barriers

The conference room buzzed with tension as Brandon Stanton pitched his unusual idea to potential investors. After being fired from his job as a bond trader, Stanton had spent months photographing strangers on New York City streets, collecting their images and stories. "I want to create a photographic census of New York City," he explained, describing what would become Humans of New York. The investors were skeptical—this wasn't a typical business model with clear monetization strategies. But Stanton wasn't seeking conventional success; he was following an intuition that human stories, simply told, could create something valuable in ways that transcended traditional metrics. Trendsetters like Stanton don't just spot emerging patterns—they create new possibilities by questioning fundamental assumptions. When Humans of New York launched in 2010, social media was increasingly dominated by carefully curated personal branding. By contrast, Stanton's project celebrated ordinary people's unfiltered stories, creating intimate connections between strangers at a time when digital culture was often criticized for promoting superficiality. The project's explosive growth—now followed by over 20 million people—demonstrated the hunger for authentic human connection that more calculated content strategies had failed to satisfy. Innovation often emerges from the margins, where people excluded from existing systems create alternatives out of necessity. Cindy Gallop, frustrated by both the advertising industry's sexism and the harmful effects of mainstream pornography, created MakeLoveNotPorn to provide realistic depictions of human sexuality. "We are socializing sex to make it socially acceptable and socially shareable," Gallop explained, describing her platform as "pro-sex, pro-porn, pro-knowing the difference." By addressing a topic most entrepreneurs avoided, Gallop identified an unmet need for honest conversation about intimate relationships—creating both a business opportunity and a vehicle for social change. Trendsetters frequently face resistance precisely because their innovations challenge established interests. When Amanda Palmer left her record label to fund her album directly through Kickstarter, industry insiders predicted failure. Instead, she raised $1.2 million from fans, demonstrating a new model of artist-audience relationship. "The music industry sees fans as consumers, not as partners," Palmer observed. Her success revealed not just a new funding mechanism but a fundamental shift in how creators could relate to their audiences—treating them as collaborators rather than customers. The most influential trendsetters combine technical innovation with emotional intelligence. Chip Kidd revolutionized book cover design not through new technology but through conceptual sophistication, creating covers that functioned as visual metaphors for each book's content. His cover for Michael Crichton's "Jurassic Park," featuring the iconic dinosaur skeleton silhouette, didn't just market the book—it became a cultural symbol in its own right. Kidd's approach demonstrated that lasting innovation isn't always about novelty but about finding the perfect form to express essential meaning.

Chapter 5: Finding Voice: Authentic Expression in Design

The art gallery fell silent as Marina Abramović sat motionless, her eyes fixed on the stranger seated across from her. For hours each day, month after month, the performance artist engaged in this wordless exchange with museum visitors—some staying for minutes, others for hours, many moved to tears by the simple act of being truly seen. "The Artist Is Present," performed at New York's Museum of Modern Art in 2010, demonstrated Abramović's extraordinary ability to transform an empty space and two chairs into a profound exploration of human connection, vulnerability, and presence. Visionaries like Abramović possess the rare ability to perceive possibilities invisible to others. While most people saw an empty atrium, she envisioned a sacred space where strangers could experience unprecedented intimacy through sustained eye contact. This capacity to see beyond current reality into potential futures distinguishes true visionaries from mere dreamers. They don't just imagine alternative worlds—they create concrete pathways to bring those worlds into being, often through work that initially appears strange, impractical, or even nonsensical to contemporaries. The visionary perspective frequently emerges from experiences of displacement or marginality. Artist Shepard Fairey, creator of the iconic Obama "Hope" poster and founder of the OBEY clothing brand, began his career with guerrilla street art that questioned advertising's dominance of public space. "When you grow up bombarded with advertising, you realize that public space has been corporatized," Fairey explained. His early "Andre the Giant Has a Posse" sticker campaign—seemingly meaningless images plastered throughout urban environments—forced viewers to question why some images in public spaces were legitimate while others were considered vandalism. Visionaries often synthesize disparate elements that others perceive as unrelated. Maria Popova's blog Brain Pickings (now The Marginalian) connects insights from literature, science, philosophy, and art to explore timeless questions about how to live well. What began as Popova's personal reading notes evolved into a beloved intellectual resource followed by millions. "I'm interested in how we can live with more presence, more meaning, and more aliveness," Popova explained, describing her work as "a record of my own becoming." By treating seemingly separate domains of knowledge as interconnected parts of a larger human conversation, Popova created a new model of cultural curation that transcends traditional academic and journalistic boundaries. The most influential visionaries transform not just what we see but how we see. Designer Tea Uglow, creative director at Google's Creative Lab, explores how technology can create more inclusive experiences for people across the gender spectrum. "Technology isn't neutral—it embodies the values and assumptions of its creators," Uglow observed. Her projects, which include virtual reality experiences that challenge binary gender perceptions, demonstrate how technological innovation can expand human empathy rather than merely optimizing existing processes. By questioning the invisible biases embedded in digital tools, Uglow helps create technology that serves diverse human needs rather than forcing humans to adapt to technological limitations.

Chapter 6: Resilience: Transforming Failure into Opportunity

The rejection letters piled up on Steven Heller's desk—nine hundred of them, to be exact—before he received his first acceptance. As an aspiring writer and designer in 1970s New York, Heller faced constant dismissal from publishers who couldn't see the value in his ideas. Rather than interpreting these rejections as evidence of his inadequacy, Heller developed what he called "generous persistence," continuing to submit work while refining his craft. This resilience eventually led to an extraordinary career spanning over 200 books on design and a 30-year tenure as art director at the New York Times. Heller's story illustrates how resilience—the capacity to persist through failure and setback—often distinguishes those who ultimately succeed from those equally talented who abandon their pursuits. While natural ability creates potential, resilience transforms that potential into actual achievement through sustained effort despite discouragement. As Heller explained, "If I have an idea, I'll wake up, I'll go to the computer, I'll write somebody with the idea, and then bug them until they tell me 'yes.'" This combination of creative vision and dogged persistence enabled him to become one of design's most prolific and influential voices. Resilience frequently requires reframing failure as valuable information rather than final judgment. When Chris Ware's early comics were met with confusion and criticism from classmates, his teacher offered perspective-shifting advice: "It's none of your business." This cryptic response helped Ware realize that his own judgment of whether his work was "good" or "bad" was less important than allowing the work to exist on its own terms. "That was the fulcrum. That's the crucial moment of my entire career as an artist," Ware reflected. By separating his creative output from his self-judgment, Ware developed the resilience to continue producing work that eventually redefined what comics could accomplish as an art form. The capacity for resilience often emerges from early experiences of adversity. Marilyn Minter, whose provocative art explores beauty and sexuality, grew up with a drug-addicted mother and alcoholic father in a chaotic household. "I was appalled by the racism and injustice I saw around me," Minter recalled of her Florida childhood. This early exposure to difficult realities developed her ability to withstand criticism when her sexually explicit artwork was initially rejected by the art world as anti-feminist. Decades later, these same works are celebrated in major museums. "If you listen to your inner vision, you make art from that place, then sooner or later the zeitgeist hits you," Minter observed. Resilience requires not just persisting through failure but learning from it to improve future efforts. When Brené Brown's first TED Talk on vulnerability went viral, she initially struggled with the sudden exposure and criticism. Rather than retreating, she studied what made her uncomfortable and developed what she calls "the arena metaphor" based on Theodore Roosevelt's "Man in the Arena" speech. "If you're going to show up and be seen, there is only one guarantee: You will get your ass kicked," Brown explained. "That is the price of admission to the arena." By accepting criticism as an inevitable part of meaningful work rather than a sign of failure, Brown developed the resilience to continue sharing vulnerable ideas despite knowing they would provoke both praise and attack.

Chapter 7: Legacy: How Creative Work Shapes Our World

The young woman sat alone in her apartment, surrounded by the debris of her former life—divorce papers, unpaid bills, and the remnants of a heroin habit she was struggling to break. At thirty-two, Cheryl Strayed had lost her mother to cancer, destroyed her marriage through infidelity, and found herself adrift without direction or purpose. In this moment of rock bottom clarity, she made an impulsive decision that would transform her life: she would hike 1,100 miles of the Pacific Crest Trail alone, despite having no backpacking experience. "I knew that if I allowed fear to overtake me, my journey was doomed," she later wrote. "Fear begets fear. Power begets power." Strayed's story illustrates how purpose often emerges not from careful planning but from moments of crisis that force fundamental reconsideration of one's path. The journey she undertook—both physical and spiritual—became not just her salvation but eventually the foundation of her career as a writer. Her memoir about the experience resonated with millions not because hiking is universally appealing, but because the underlying journey of finding oneself through difficult challenges speaks to a universal human quest for meaning and direction. Purpose frequently reveals itself through unexpected detours rather than direct pursuit. Tim Ferriss, author and podcast host, discovered his calling through a series of apparent failures. After being rejected from his dream job at a prestigious consulting firm, Ferriss started a nutritional supplements company as a stopgap measure. This "temporary" business became the laboratory where he developed the time management and delegation strategies that would later form the basis of his bestselling books. "What appears to be a setback or failure is often the universe redirecting you toward something better aligned with your true purpose," Ferriss observed. The search for purpose often requires reconciling contradictory aspects of oneself. Elizabeth Alexander, poet and academic, struggled to integrate her scholarly identity with her creative voice until a transformative encounter with mentor Derek Walcott. Looking through Alexander's diary, Walcott recognized poetry in what she had dismissed as mere "word clouds." Taking one passage, he wrote it out with line breaks, saying, "See, you're writing poems, but you don't know how to break lines, and that's what makes it a poem." This moment of recognition—seeing artistic purpose in what had seemed like private musings—launched Alexander's career as a poet, eventually leading to her reading at President Obama's inauguration. Finding purpose often requires letting go of external validation to pursue what feels internally meaningful. Seth Godin abandoned a successful career in traditional publishing to become one of the internet's earliest content creators, writing daily blog posts since 2002. "I thought I had something to say, but I also believed that by frequently and generously showing up in front of people who wanted to hear from me, I would earn their trust," Godin explained. Rather than measuring success through conventional metrics like book sales or academic citations, Godin focused on consistently providing value to his audience—a purpose-driven approach that eventually made him one of the most influential business thinkers of his generation.

Summary

Throughout these stories of creation and transformation, we witness the extraordinary power of persistence through uncertainty. Milton Glaser's ethical framework for design, Brené Brown's research on vulnerability, Cheryl Strayed's wilderness journey—each reveals how creative breakthroughs often emerge from periods of profound discomfort. The legends, truth-tellers, culture makers, trendsetters, and visionaries profiled here share a common willingness to remain open and engaged even when the path forward seems unclear. As Lynda Barry discovered when her drawing teacher told her "It's none of your business" whether she liked her own work, creative transformation often requires suspending judgment long enough to allow something new to emerge. The most valuable insight these stories collectively offer is that meaningful lives are designed through continuous acts of creation rather than discovered fully formed. Whether through Alison Bechdel's painstaking documentation of family dynamics, Brandon Stanton's street photography, or Maria Popova's intellectual curation, we see how purpose emerges through action rather than preceding it. The courage to begin without guarantees—to make the first sketch, write the first sentence, or take the first photograph—initiates a process that gradually reveals our unique contribution. As Seth Godin observed, "We're bad at experiencing the future and we're excellent at experiencing the present." By focusing on creating value in the present moment rather than predicting outcomes, we design lives that remain adaptable to unexpected opportunities and resilient through inevitable setbacks.

About Author

Loading...

Debbie Millman

Debbie Millman is an American writer, educator, artist, and designer who is perhaps best known as the host of the Design Observer podcast 'Design Matters'. She is 'President of Design' at Sterling Brands, based in New York City, working with brands such as Pepsi, Gillette, Colgate, Kimberly-Clark, Nestlé, and Campbells. She chairs the 'Masters in Branding' program at the School of Visual Arts, is a contributing editor to Print, a blogger for Fast Company, and the 'President Emeritus' of AIGA.

Read more