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What if great communication isn’t about saying more, but saying what actually matters? Sarah Kissko Hersh has spent more than two decades inside agencies, brands, and leadership rooms where words carry weight. She grew up in Indiana, built her career in Chicago and New York, and learned early that clarity, not polish, is what moves people forward. Along the way, she worked across architecture, design, travel, luxury, and global firms, often stepping into messy moments where teams felt stuck and leaders felt unsure of what to say next. What started as a traditional PR career slowly evolved into something deeper. Sarah saw how often people were promoted into leadership without being taught how to manage. How communication broke down not because of bad intentions, but because of fear, burnout, and lack of direction. And how simple, honest language could reset entire teams. Today, Sarah is the founder of Type A, a communications and leadership consultancy based outside New York City. Her work focuses on helping people get unstuck, communicate directly without losing kindness, and lead with clarity in moments that matter. In this conversation, Sarah and Justin talk about what PR really is and what it is not. Why simple stories still win. How bad managers can teach you just as much as good ones. Why constraints often unlock better ideas. And how platforms like LinkedIn are less about self-promotion and more about learning to name what you already know. For leaders, creatives, and communicators, this episode is about making work feel lighter without making it shallow. About learning while you laugh. And about remembering that the most effective communication is deeply human. What You’ll Learn + Clarity beats complexity. Simple, honest language builds trust faster than polished noise. + PR is about truth, not spin. Good communication starts with what’s real. + Leadership is learned. Managing people requires skills most of us were never taught. + Fear keeps teams stuck. Naming it is often the first step forward. + Constraints spark creativity. Less can actually lead to better ideas. Why It Matters Sarah’s perspective reminds us that communication is not a soft skill. It is leadership in action. Whether you manage a team, tell stories for a living, or simply want to be understood at work, this episode shows how clarity, humor, and care can change the way people listen and respond. Listen Now If this conversation made you laugh, think, or see your work a little differently, share it with someone who leads, writes, or communicates for a living. Follow Design Of wherever you listen, and keep building work that helps people understand what truly matters.

What if the most powerful kind of creativity isn’t about making things beautiful, but making them clear? Gordon Kaye never planned to work in design. He studied law, built a career in New York, and handled media and trademark cases before joining NBC as counsel, reviewing everything from late-night jokes to broadcast standards. But when his father’s health declined, he stepped away from law to take over the family publication, Graphic Design USA (GDUSA), a magazine his father had launched in the 1960s to celebrate the people behind design, not just the work itself. What began as a rescue mission became a lifelong calling. Gordon brought his legal mind and curiosity for communication to a creative field that thrives on clarity. Over the decades, he’s evolved GDUSA into more than a design magazine, it’s a respected voice for how ideas move through business, marketing, and culture. In our conversation, Gordon and Justin talk about what design can teach every leader: how to communicate simply, lead with empathy, and build trust through the way we share information. They discuss how his outsider’s view helped him see design not as decoration, but as direction. And how clarity, when done well, can turn creative thinking into real influence. For business and marketing leaders, this episode is about more than design. It’s about the responsibility of communication. About how we help people see what matters. And how legacy, when guided by purpose, can evolve without losing its truth. What You’ll Learn + Clarity earns influence. The best ideas don’t need to shout—they need to be understood. + Every message is designed. The way you shape words, visuals, or decisions defines how people respond. + Legacy means evolution. True leadership honors the past while adapting to what’s next. + Trust is the real deliverable. In every field, communication rooted in honesty connects. + Purpose over polish. Simplicity, empathy, and meaning will always outperform noise. Why It Matters Gordon’s journey, from NBC’s legal floors to the heart of the design community, proves that communication is leadership. You don’t have to be a designer to think like one. You just have to care about how people understand you. Listen Now If this episode helps you think differently about how you lead, share it with someone who shapes communication where you work. Follow Design Of wherever you listen, and keep building teams, messages, and brands that people can trust.

What happens when you stop chasing views and start designing for belonging? When the world went online, most virtual events started to feel the same, flat, distant, and forgettable. But not for Rachel Elnar, Heather Lynn, and David Carr-Berry. Together, they built some of Adobe’s most loved digital experiences: Creative Jams and The Perfect Match, a 1970s-style design game show complete with music, lights, wigs, and real connection. These weren’t webinars. They were living, breathing events that made thousands of creatives feel seen. Each brought something vital: Rachel’s heart for community, David’s director’s eye for rhythm and flow, and Heather’s producer’s instinct for care and calm. Their shared secret? Treat every audience like a room full of humans. When layoffs hit, they took that shared language and built something new: Together By Design—a creative studio helping others build programs with purpose, host events with empathy, and grow communities that last. This is a conversation about saying yes to collaboration, honoring craft, and leading with care in a digital world that often forgets what connection really means. In This Episode + What makes a live event feel alive, and how to design for it + The small touches that make an audience feel seen + Why systems and empathy are equally important behind the scenes + The difference between an audience and a community (and why it matters) + A behind-the-scenes story of a live show gone wrong, and what it taught them + Why joy and structure are the true foundation of creative work Guests Rachel Elnar is a creative producer, designer, and founder of Together By Design. She previously led Adobe’s Creative Jam program, helping thousands of designers connect and grow. Heather Lynn is a digital events producer and educator who helps speakers and teams show up with confidence, presence, and calm. David Carr-Berry is a director who sees live production as choreography for people, story, and emotion, and loves when the unexpected brings beauty. Key Takeaways + Design events for belonging, not performance + The most powerful tool in live work is empathy + Systems create space for spontaneity and joy + Building community requires care before, during, and after the show + When you respect your audience, they’ll keep showing up The Heart of It At its heart, this episode is about something bigger than events. It’s about presence. About noticing the people on the other side of the screen. Because when we create with care, whether it’s a meeting, a mural, or a moment—we remind the world what it feels like to be together.

What if the most honest way to change minds isn’t a new campaign, but a new way to see familiar things? Brian Singer, known as “Someguy,” makes work that lures us with beauty and play, then nudges us to sit with what’s uncomfortable. Brian’s projects cross gallery walls and public space. The 1000 Journals Project sent blank books into the world for strangers to fill. TWIT Spotting put photos of distracted drivers on billboards to make a daily danger impossible to ignore. His recent pieces deconstruct books, flags, and everyday objects to examine censorship, identity, and what we choose to remember. In this conversation, we talk about how design craft and social commentary can live together. We also talk about heritage, silence, and what it means to make work that is both kind and clear. For the Rule29 community, this is a practical lens for client work and culture. Brian shows how to use material, language, and context to create meaning. He shows why public engagement matters. And he reminds us that strong ideas don’t need to shout. They need to connect. Brian Singer is a San Francisco artist and designer. His work has been exhibited at SFMOMA, the Skirball Cultural Center, and the Torrance Art Museum. The 1000 Journals Project became a book and a feature documentary. He has led design for brands like Apple, Adidas, and Chronicle Books, and served as AIGA SF president. What you’ll learn: + Make the familiar new. Reframe common symbols. Use deconstruction and reconstruction to reveal hidden meaning. + Design for public impact. Borrow trusted forms. Invite participation. Meet people where they are. + Beauty is a strategy. A clean, striking form opens the door. The message keeps people in the room. + Hold tension with care. Pair empathy with truth. It is possible to be humane and direct. + Build time into ideas. Let projects evolve. Some work needs years, not weeks. + Lead with context. Materials matter. Where a piece lives changes what it says. If you want work that moves people, don’t add more noise. Create encounters. Give your audience a role. Use your craft to lower defenses, then be honest about the issue. This approach works in public art, brand systems, and campaigns. It also builds trust. If this episode gives you one nudge, let it be this: pick one symbol you use every day and ask what it really says. Then design a way for someone to see it fresh. That’s how change starts. Thanks for listening to Design Of. If this conversation helped you think differently, share it with one person who leads creative work. Leave a rating where you listen. And keep making work that tells the truth with care. Links and references for episode: https://someguy.is/

What happens when you say yes to what brings you joy, even if it starts on the side? For Chicago-based artist and designer Alyssa Low, it began with a quiet sketch. A visual diary during the early days of the pandemic. “I was just trying to express what I was feeling, when words didn’t quite work,” she says. That simple practice of showing up for herself turned into something bigger. One mural became two. Then came the collaborations: Wayfair. The Chicago Bulls. Soho House. Public art that now lives across city walls, basketball courts, patios, and even 10,000 hats handed out at a Bulls game. Alyssa is a multidisciplinary artist and muralist whose work is rooted in bold color, community connection, and movement. But she still holds a full-time design job. And she still approaches every project with the same focus and curiosity that shaped her as a kid, watching her mom run a design studio out of their home, playing competitive soccer, and practicing Tae Kwon Do forms that taught her how to focus, adapt, and flow. I n her words: “If it brings me joy, I keep going. That’s when the best work shows up.” I n this episode, Alyssa shares: + How to build something meaningful, while still working full-time + The moment murals “clicked” and what made her say yes before she felt ready + What it felt like to see thousands of people wearing her design at a Bulls game vHow sports and martial arts helped her find her rhythm as an artist and entrepreneur vWhy staying connected to identity, culture, and community gives her work purpose Whether you’re a creative, a leader, a builder, or simply someone figuring out what’s next—this story is a reminder to pay attention to what lights you up. Because sometimes, the most important step is simply starting. 🎧 Listen to The Design Of Bold Joy wherever you get your podcasts. #DesignOfPodcast #AlyssaLow #CreativeJourney #SideHustle #PublicArt #Murals #ChicagoCreatives #Identity #Leadership #JoyAtWork #BoldJoy

What happens when a designer at the top of his field walks away to chase something simpler, sharper, and harder? Illustrator Craig Frazier did exactly that, leaving a thriving design practice for a life defined by clarity and metaphor. Craig shares how he built a signature style that makes the complex instantly understandable. From Time magazine covers to U.S. postage stamps, his work proves how powerful reduction can be, and why the best ideas often live just shy of obvious. We talk about the moves that changed his career: a humble self-promo that landed Time magazine, a decade-long brand system made of pictures not paragraphs, the discipline of offering three strong options, and why clarity comes from pulling back just before obvious. Craig Frazier is an illustrator, designer, and author whose clients include The New York Times, The Wall Street Journal, Adobe, and the U.S. Postal Service. His work is known for clarity, wit, and staying power. In this episode, you’ll hear: + Why Craig left a successful design firm to pursue illustration full time + How clarity, reduction, and metaphor became the foundation of his style + Lessons from projects ranging from national publications to U.S. postage stamps + The role of trust, discipline, and play in creative problem-solving + Why leaping into uncertainty may be the only way to grow as a creative and leader “There’s not just one solution to everything. The rightness of a solution has to do with its measurement against an objective, not personal taste.” – Craig Frazier Clarity, metaphor, and discipline aren’t just tools for illustrators, they’re lessons for anyone leading, communicating, or building something that lasts.

What if the most powerful brand you could build didn’t shout, it whispered, “You’re enough”? That’s the quiet revolution Miss Katie Sings is leading. In this episode of Design Of, we sit down with Katie Norregaard, aka Miss Katie Sings, a musician, educator, and content creator who’s redefining what it means to connect with your audience. With calm clarity and cultural depth, she’s grown from a single homemade video during lockdown to a trusted global presence in children’s music, simply by being herself. She didn’t launch with a marketing team or a strategy deck. She launched with a box of rice as a drum, a $0 brand name, and an unwavering belief that kids deserve better. Her presence, gentle, intentional, and deeply human, has drawn comparisons to Mister Rogers. Not because she imitates him, but because she shares his radical belief: that children deserve to be seen, heard, and taken seriously. Here’s why this one’s worth your time: Because Katie’s story is what every brand leader, creative, educator, or purpose-driven entrepreneur needs right now, proof that authenticity scales, and that the right voice can cut through the noise by being exactly what the world needs: human. And if you’re simply someone trying to be a good human yourself, this story will remind you how much impact one kind, clear voice can make. In this episode, you’ll hear: + How “I Am Enough” became a viral anthem for emotional resilience + Why Miss Katie’s Mr. Rogers-style calm is her brand, and a differentiator + How representation and anti-bias education are built into her content strategy + What it means to grow a community by showing up gently but consistently + How a non-flashy approach became her biggest competitive advantage + Stories that reveal the real impact of leading with empathy and intention “You can be loved exactly as you are.” It’s not just a lyric. It’s a strategy, and a reminder. Whether you’re building a brand, telling a story, or trying to connect more deeply with your audience, this episode is a blueprint for how powerful simplicity and honesty can be. 🎧 Listen to Design Of: Feeling Enough with Miss Katie Sings, and rethink what it really means to resonate. https://www.misskatiesings.com/

What if your next competitive advantage wasn’t a new product, but a new kind of leader? Doug Powell believes designers and design thinkers have the skills business needs most right now, the ability to connect human needs with strategic goals, to navigate uncertainty, and to see opportunities others miss. In a world of rapid technological change and economic contraction, that perspective can be the difference between falling behind and defining what’s next. Doug has spent his career proving it. At IBM, he helped build one of the largest corporate design programs in history, hiring over 1,000 designers, embedding human-centered design across global teams, and aligning design thinking with enterprise strategy. He’s led at the highest levels of AIGA, advised Fortune 100 leaders, and now coaches executives on how to integrate design into the core of their decision-making. This is an essential time for design and designers. In the face of unprecedented global challenges and a rapidly evolving technological landscape, the core skills of human-centered design, empathy, curiosity, inclusion, collaboration, and craft, are needed more than ever. Doug believes designers are made for this moment. For business leaders, Doug’s perspective is a wake-up call: designers and design thinkers are not just executors of creative work, they are catalysts for innovation, culture change, and long-term growth. Research from McKinsey shows that companies excelling in design outperform industry peers by up to 2x in revenue growth and shareholder returns. A 2023 InVision report found that 92% of high-maturity design organizations report a strong connection between design and business strategy. Doug argues that in a time of technological disruption and market uncertainty, leaders who integrate human-centered design into the decision-making core of their companies will be the ones defining what’s next. In this conversation, you’ll hear about: + Why companies that integrate design at the leadership level grow faster and create greater shareholder value +Lessons from building IBM’s global design program from scratch in under four years +How human-centered design can break down silos and speed decision-making across functions +Why downturns are a prime opportunity to invest in innovation and talent +The lasting influence of Tibor Kalman and the responsibility of design to challenge complacency +How AIGA builds leadership capacity across industries and the value of giving back +Why designers will be at the center of AI’s most transformative breakthroughs, and what leaders should do now Whether you’re a CEO, CMO, or innovation lead, this episode will show you how to harness design as a strategic advantage, not just for better products, but for stronger teams, sharper strategy, and sustainable growth.

Billy Oppenheimer is a pattern-seeker, storyteller, and creative thinker who turns curiosity into clarity. His path, from ski towns and side jobs to working alongside bestselling author Ryan Holiday, is a powerful reminder that following what fascinates you isn’t a distraction; it’s a direction. In this episode of Design Of, Billy shares how his instinct to notice, capture, and connect ideas has shaped his creative journey, and how it continues to evolve through deep research, disciplined writing, and his upcoming book with Penguin Random House, The Work Is the Win. Billy’s creative trajectory began with a bold, curiosity-fueled email to Ryan Holiday, whose own career was launched under the mentorship of Robert Greene (The 48 Laws of Power). That lineage, Greene to Holiday to Oppenheimer, reflects more than just professional mentorship. It reveals a shared creative philosophy: do the work, think deeply, and trust that the process itself holds the reward. Now, through his widely followed newsletter Six at Six, Billy shares six thought-provoking quotes every Sunday evening. What began as a personal archive has become a trusted source of insight for thousands of creatives, leaders, and lifelong learners looking to build their lives, and their brands, with greater purpose and intention. This is a conversation for leaders, storytellers, and anyone building something that matters. Billy doesn’t offer hacks, he shares a mindset and a method. One rooted in showing up, tuning in, and trusting that the work is always worth it. In this episode, you’ll hear: + Why “the work is the win”, and how process over outcomes leads to deeper fulfillment + How his note card system fuels storytelling, pattern recognition, and long-term creative value + What he learned from working with Ryan Holiday and through the influence of Robert Greene + How Six at Six became a trusted source of wisdom for thousands + What his upcoming book The Work Is the Win reveals about building a life through curiosity + How to turn inspiration into a personal archive of insight and meaning + Why curiosity is a compass, not a detour “None of it is wasteful. Every job, every quote, every story, it all has a place.” Whether you’re leading a brand, guiding a team, or searching for your next creative spark, this episode is a powerful invitation to slow down, notice more, and trust the work. 🎧 Listen now to Design Of: The Work Is the Win , and rediscover the value of following what fascinates you.

Jerry Takigawa is a rare kind of thinker, someone who approaches the world not just with creativity but with deep awareness, humility, and care. His work as an artist and storyteller explores what it means to carry a legacy, reframe pain into purpose, and make meaning in a world that often feels fragmented. In this episode of Design Of, Jerry shares how his Japanese American heritage, his parents’ experience with internment, and his lifelong creative practice have shaped the way he see, and responds to, the world. This is a conversation for leaders, creators, and anyone navigating complexity. Jerry doesn’t just talk about ideas, he embodies a way of thinking that invites reflection, connection, and change. You’ll hear: + Why embracing uncertainty can lead to more authentic leadership + How silence and heritage shape our voice, and our responsibility vWhat it means to create from both logic and intuition + How storytelling, metaphor, and vulnerability unlock deeper trust + And why making space for meaning is essential to resilience and growth One of the most powerful ideas Jerry shares is this: “Your thinking is genesis, and your actions are contagious. So what is worth doing?” Whether you’re building a business, guiding a team, or simply trying to live with more intention, this conversation is a meaningful invitation to pause, look closer, and move forward with greater clarity. 🎧 Listen now to Design Of with Jerry Takigawa, and explore how the way you see the world shapes the way you change it. To dive deeper into Jerry’s philosophy, we highly recommend his book, Grace in Uncertainty: A Designer’s Search for Meaning. You can explore it here: 👉 https://www.takigawadesign.com/grace-in-uncertainty

Ali Schwanke isn’t just a marketer, she’s a builder of trust, a champion for clarity, and a quiet force of curiosity. As the founder of Simple Strat and the face of HubSpot Hacks (with over 3 million views and counting), Ali has become one of the most trusted voices in helping businesses unlock their true potential, not just in tools, but in people. In this episode, we trace Ali’s journey from a childhood of small-town hustle, selling greeting cards door-to-door, to becoming a sought-after strategist who sees marketing as more than data and automation. For Ali, marketing is about heart: the stories we tell, the ways we listen, and the empathy that holds it all together. Along the way, we explore: + Why “helping is the new selling” became her mantra + How she navigates the balance between data and human connection + What it means to stand out in a world of noise and sameness + The emotional power of B2B marketing—often overlooked, but never absent + And how Ali sees growth as an experiment in courage and care Ali’s story is a reminder that the best businesses, and the best leaders, start by understanding people. They’re built on curiosity, driven by service, and never stop learning. In this episode, you’ll hear: + Why empathy is more than a buzzword, it’s a competitive advantage + How Ali built a company that leads with clarity and connection + The challenges and joys of turning curiosity into action + And why the future of marketing might just belong to those who aren’t afraid to help first Whether you’re refining your brand, growing your team, or rethinking your approach to connection, this conversation is for anyone who believes that real impact is built with both heart and hustle.

Peter Aguero isn’t just a performer, he’s a presence. Known for his emotionally charged, wildly entertaining, and deeply human stories, Peter has become one of the most beloved voices in the storytelling world. A longtime host and GrandSLAM champion with The Moth, Peter’s work explores grief, rage, love, redemption, and the quiet moments that define who we are. In this episode, we sit down with Peter to trace the creative arc of his life, from growing up in South Jersey and leaving football behind, to traveling the country with Chicago City Limits, and eventually becoming a core figure in The Moth’s rise to cultural prominence. Along the way, we explore why storytelling isn’t just communication, it’s how we make sense of being human. Peter’s story intersects with some of the greats, including his longtime friendship with creative musician and experimental educator Dave Gould, who introduced him at a transformative moment in Iowa City. Together, their work reminds us that story is not just scientific, it’s deeply experiential. It’s memory. It’s identity. It’s the way we heal, connect, and lead. We also revisit some of Peter’s most memorable performances, including: “You’re Not Alone” (The Moth Mainstage, Metropolitan Museum of Art), a heartbreaking and healing story about Christmas with his mother “The Italian Ice Fight” — a wild, true tale about a summer job that ended with a hammer, a fight, and a lesson in fear Daddy Issues (his one-man show) — a raw, theatrical journey through masculinity, shame, and survival Appearances on Conan and in venues like the Bitter End, Highline Ballroom, and under-the-radar NYC gems like Under St. Mark’s In this episode, you’ll learn: + How vulnerability builds creative credibility + Why your real voice is more powerful than your polished one + How to structure stories that resonate emotionally, without overproducing + What brands and leaders can learn from live storytelling and audience honesty + How to tell stories that invite recognition, not just applause Whether you’re leading a brand, creating a presentation, or trying to inspire others, this episode is a reminder that the most unforgettable stories are the ones that don’t try too hard. They just tell the truth.

If you’re a business leader, creative director, entrepreneur, or someone curious (or even a little anxious) about how AI fits into your work, this episode is for you. In this conversation, Justin Ahrens talks with Scott Meyer, co-founder of Chipp.ai, about designing AI tools that don’t just automate, but amplify creativity, strategy, and human connection. Scott’s journey, from studying peace and conflict in Norway to building tech startups. has always centered on clarity, access, and community. Together, they explore what it means to make AI more human, more useful, and more aligned with how we actually think, lead, and create. In this episode, you’ll discover: + Why now is the best time to start exploring AI (even if you’re intimidated) + How to build your own “digital protégé” that thinks and sounds like you + New ways AI can streamline marketing, strategy, and internal operations + How curiosity and courage, not technical skills, are the real superpowers + And why “At Last” by Etta James might be the perfect anthem for embracing new technology This episode is packed with real stories, honest insights, and practical ideas to help you move from hesitation to confidence, and integrate AI into your business and brand with purpose, creativity, and heart. 🔗 Recommended Links: Chipp.ai – Build & deploy your AI assistants: https://chipp.ai Chipp on YouTube: https://www.youtube.com/@chippai

“Music is completely emotion-driven for me. If I don’t feel it, I can’t fake it. That’s why I keep writing, to stay close to that feeling.” In this deeply reflective episode of The Design Of, Justin Ahrens sits down with musician, composer, and sonic storyteller Ryan O’Neal, best known as Sleeping At Last. With millions of listeners around the world and a body of work that’s as emotionally rich as it is expansive, Ryan shares how he intentionally designs not just music, but meaning. We explore how Ryan’s creative process is rooted in emotion, curiosity, and the desire to stay connected to what truly moves him. From writing songs inspired by the Enneagram to scoring film and television, Ryan talks about chasing wonder, navigating vulnerability, and using music as a mirror for growth. While Ryan is a musician, his approach offers powerful insights for anyone in business, branding, or leadership. His creative process models how to: + Lead with emotional intelligence, understanding the power of empathy in connection + Tell stories that resonate, by tapping into universal emotions and personal truths + Build a brand with heart, that earns trust, loyalty, and long-term impact + Design experiences that feel human, not just polished If you're trying to inspire teams, connect with customers, or create more meaningful marketing—this episode will remind you why feeling is often more powerful than strategy alone.

Andy Stoll is the guy you want at your dinner party if you're looking for some serious entrepreneurial wisdom mixed with a dash of world-traveler intrigue. As a Senior Program Officer in Entrepreneurship at the Kauffman Foundation, he's got a cool $25 million philanthropic portfolio to work with, all in the name of strengthening entrepreneurship and innovation across the United States. This Omaha native with family roots in a small Japanese farming community in western Nebraska embarked on a four-year solo trip around the world, visiting a whopping 40 countries. He's been inspired ever since, founding not one, not two, but six entrepreneur-focused companies over the past two decades. Throughout his career, Andy has collaborated with industry leaders such as Steve Case, Paul Allen, and Tony Hsieh. He's now considered one of the leading national voices on how cities can build more vibrant and equitable entrepreneurial communities. From working in Bollywood to living in a mud hut village in Zambia, and even teaching apple pie making on Armenian National television, this guy's life is like a travel documentary of experiences. He also moonlights as a photographer, sometimes chef, and cooking class instructor. You might be asking yourself…Is there anything this guy hasn't done? We're not sure, but we can guarantee that he'll bring some serious insight and a good story or two to any podcast he's on. Don't miss out on hearing from this multi-talented entrepreneur.