Hosted by with host Justin Ahrens · EN

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.

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.