In this episode, we dive into how complexity creeps into our systems—whether in software, organizations, or personal leadership. We start by looking at the evolution of Microsoft Word as a case study of feature creep and unintended consequences, asking why more options can end up stifling creativity. We’re joined by Robert Siegel , Stanford lecturer and author of The Systems Leader , who unpacks why today is a uniquely chaotic time for leaders. He explores the cross-pressures leaders face—from balancing execution with innovation, to combining strength with empathy—and what it takes to thrive in turbulent environments. Later, we revisit a powerful 2017 conversation with Seth Godin , bestselling author and entrepreneur. Seth reframes uncertainty as an inherent feature of modern systems, not a personal failure. He shares his perspective on adapting to continual change, why embracing smaller markets and iterative progress makes us more resilient, and how redefining success helps us stay in the game. Whether you’re leading a team, navigating constant change, or just trying to keep your work meaningful, this episode will give you fresh strategies for thinking and acting systemically. Five Key Learnings: Complexity Creep Is Real: As with Microsoft Word, adding features to solve edge cases often leads to more user frustration and less creative freedom. Simplicity can be a competitive advantage. Systems Leadership Is Essential: Leaders must operate with a systems mindset, recognizing the interconnectedness inside and outside their organizations rather than staying siloed. Balancing Dualities: Success today means navigating cross-pressures, such as execution vs. innovation and strength vs. empathy—not just picking one. Embrace Uncertainty: Uncertainty isn’t going away; learning to see it as a product of changing systems makes it less personal and more navigable. Iterate and Focus Small: Applying your creative efforts to the smallest viable audience allows for better learning, less risk, and greater long-term impact. Get full interviews and bonus content for free! Just visit DailyCreativePlus.com . Mentioned in this episode: Apply for Creative Leader Roundtable Leading creative people is rewarding, but it can also feel isolating. That's why I've started Creative Leader Roundtable, a private community where leaders like you connect monthly to get practical insights, honest feedback, and real encouragement. You'll leave every round table with fresh perspective and tactical ideas. You can apply right away. So if you lead a team of talented people, go check us out at CreativeLeader.net , because creative work deserves brave leadership. The Brave Habit is available now My new book will help you make bravery a habit in your life, your leadership, and your work. Discover how to develop the two qualities that lead to brave action: Optimistic Vision and Agency. Buy The Brave Habit wherever books are sold, or learn more at TheBraveHabit.com .
