The Many Ways to Slice a Watermelon: A Design Journey with Vitaly Friedman

Nov 6, 2025

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What can slicing a watermelon teach us about design? Turns out… quite a lot. This week, I chat with Vitaly Friedman, founder of Smashing Magazine, to explore curiosity, inefficiency, and why the best designers obsess over process, not perfection.

What if your next design breakthrough came not from a book or a course, but from learning to slice a watermelon?

Vitaly Friedman has spent decades shaping how designers think about the web. But in this conversation, we go beyond pixels and patterns to talk about something much more profound: how curiosity itself becomes a design tool. From choosing the perfect watermelon to mastering the art of ironing, Vitaly reveals how everyday obsessions can teach us how to think, learn, and design better.

We explore how designers can reclaim joy and curiosity in their work, especially in environments where efficiency and productivity often come at the expense of creativity. Vitaly’s take? It’s not about finding the perfect way to do something—it’s about exploring many ways and discovering meaning in the process.

From grilled watermelons to enterprise UX, we connect the dots between experimentation, self-learning, and the messy human side of design.

If you’ve ever felt stuck chasing “best practices” or trying to find the “right” answer, this episode will remind you that sometimes, the most valuable thing you can do is play.

Topics:
• 03:39 – The Watermelon Metaphor
• 05:37 – Choosing the Perfect Watermelon
• 09:19 – Cutting Techniques and Presentation
• 13:34 – Grilling Watermelon and Culinary Creativity
• 14:28 – Learning and Self-Education
• 15:13 – The Journey of Exploration
• 18:28 – Imposter Syndrome and Asking for Help
• 22:00 – Humanizing Executives and Stakeholders
• 22:48 – The Importance of Curiosity
• 25:34 – Ironing and Finding Zen
• 30:01 – The Role of Enjoyment in Learning
• 31:35 – Procrastination and Productivity
• 33:46 – Procrastination and Focus
• 34:48 – Memorable Conference Experience
• 37:08 – Finding Joy in Enterprise UX Design
• 38:50 – Challenges in Enterprise Projects
• 41:35 – Building Trust and Team Culture
• 50:50 – Balancing Exploration and Delivery

Helpful Links:
• Connect with Vitaly on LinkedIn
• Smashing Magazine
• Design Patterns For AI Interfaces

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