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.
His 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, Oppenheimer 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. Oppenheimer 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.
Billy Oppenheimer
The Design Of podcast shares inspiring conversations on how people design their lives to create extraordinary projects, impact, and careers. Hosted by Justin Ahrens, founder and Chief Creative Officer of Rule29, each episode explores the stories behind creativity, purpose, and leadership. Ahrens sits down with designers, entrepreneurs, story, and makers to uncover how they built a life and work with meaning.
Follow Design Of on X or visit Design Of on the web to learn more and listen to past episodes.
The post The Design Of The Work is The Way With Billy Oppenheimer appeared first on PRINT Magazine.