Sam Seidel and Olatunde Sobomehin on the Creative Hustle and Blazing Your Own Path

On this episode of the Getting Smart Podcast, Tom Vander Ark is joined by repeat podcast guest Sam Seidel Director of K12 Strategy + Research at the Stanford d.school, the Hasso Plattner Institute of Design at Stanford University and Olatunde Sobomehin, CEO of StreetCode Academy to discuss their new book Creative Hustle: Blaze Your Own Path and Make Work That Matters. 

Tom Vander Ark: All right, Olatunde, what is Creative Hustle?

Olatunde Sobomehin: I’m glad you asked. Creative Hustle is obviously this book we just wrote and a class Sam and I taught. But beyond that, it’s about living beyond your limits. It’s about creating your own path, especially in a world where so much is predetermined for us—like where we live, who we’re married to, how much melanin is in our skin. These are things people use to predict where we’re going to be. But Creative Hustle is about living beyond that. “Creative” is the bigness of it; “Hustle” is the day-to-day approach. We talk about it as imagination plus ambition—that’s Creative Hustle.

Tom Vander Ark: I’m Tom Vander Ark, and you’re listening to the Getting Smart podcast. We’re joined today by Olatunde Sobomehin, CEO of Street Code Academy, and his co-author, Sam Seidel.

Sam Seidel: Thanks for having me, Tom. It’s good to be back and to be here with Olatunde.

Tom Vander Ark: There’s such cool stuff happening at the d.school. I just found out that this book is part of a series. Can you tell us about that?

Sam Seidel: Yeah, we have a series of 12 books coming out through a collaboration with Ten Speed Press, a subsidiary of Penguin Random House. Ten Speed specializes in putting out beautiful books, and it’s been exciting to work with them on this series. This book we’re talking about today, Creative Hustle: Blaze Your Own Path and Make Work That Matters, is part of that.

Tom Vander Ark: We reviewed a book by your colleague Sarah Stein Greenberg recently. It’s an amazing collection of exercises and insights about creative thinking. How does Creative Hustle fit into that series? What makes it unique?

Sam Seidel: Creative Hustle fits into the series as a guide specifically focused on helping people navigate the intersection of creativity and ambition. The idea is to inspire readers to pursue work that’s meaningful to them while giving them practical tools to take steps in that direction. It’s a bit different from Sarah’s book, which focuses more on creative processes and tools for design thinking. Our book leans more into personal and professional development, especially for people who may not see themselves fitting into traditional career paths but still want to make a real impact.

Olatunde Sobomehin: Exactly. The book is for anyone trying to find their way in a world that’s often rigid about what paths are “acceptable” or expected. We wrote it for people who may feel like outsiders, who want to do something meaningful but don’t necessarily have a blueprint for it. Creative Hustle gives permission to imagine bigger and to hustle every day toward that vision.

Tom Vander Ark: I love that. The idea of imagining bigger while also hustling in a grounded, daily way is powerful. It sounds like a message that could resonate with students, young professionals, or really anyone looking to carve their own path. How did the idea for the book originate?

Olatunde Sobomehin: The book originated from a class that Sam and I taught at the d.school. The class was about blending creativity with practical ambition, showing students that they could pursue passions and make an impact without fitting into predefined boxes. The class got a great response, and we realized that the concepts we were teaching resonated with a lot of people beyond our classroom. We thought, why not share these ideas with a wider audience? So, we decided to turn it into a book.

Sam Seidel: And the class itself was born from our own experiences of navigating life and work. Both Olatunde and I have pursued paths that don’t necessarily align with traditional expectations. We both believe in dreaming big but also in putting in the daily grind to make those dreams happen. We saw that there was a need to talk about this blend of creativity and hustle, especially for people who might not have traditional roadmaps for success. So, the book is both a reflection of our own journeys and a tool to help others on theirs.

Tom Vander Ark: That’s awesome. You mentioned the idea of being “outsiders.” I’d love to hear more about how you think the concept of Creative Hustle applies to people who might feel marginalized or like they don’t fit into traditional career frameworks.

Olatunde Sobomehin: I think Creative Hustle is especially relevant for people who have historically been on the margins or who feel like they’re not represented in mainstream spaces. For people who don’t see their communities, their stories, or their dreams reflected in what’s presented as “normal” or “successful,” it can feel like they’re hustling against the grain. Creative Hustle encourages them to take control of their narrative and make space for themselves in ways that might not be traditional but are still powerful and impactful.

Sam Seidel: Yes, and the whole point is to celebrate those nontraditional paths. Sometimes, the things that make someone feel like an outsider are actually their superpowers. Whether it’s a unique perspective, a different cultural background, or life experiences that don’t fit into a conventional mold—those can all be assets in creating something new and meaningful. The book encourages people to lean into those parts of themselves and use them as fuel for their creative journey.

Tom Vander Ark: I love that approach. In Creative Hustle, are there any specific stories or examples of people who embody this blend of creativity and ambition?

Sam Seidel: Yes, definitely. We share several stories of individuals who have forged unique paths by combining creativity with a relentless work ethic. One example is a young woman who grew up in a rough neighborhood, became a designer, and used her skills to bring positive change to her community. Another story is about a man who turned his love of sneakers into a successful business while giving back to youth in his city. These are people who might not have had traditional opportunities or support systems but who found ways to leverage their passions and skills to make an impact.

Olatunde Sobomehin: We also talk about our own experiences and the challenges we faced. We didn’t follow standard career paths, and we both encountered obstacles along the way. But through Creative Hustle, we were able to turn those challenges into stepping stones. The book is filled with practical exercises and real-world advice to help readers do the same—whether they want to launch a project, start a business, or make a difference in their community.

Tom Vander Ark: That’s fantastic. You mentioned practical exercises—what kind of exercises are included in the book to help people take action?

Olatunde Sobomehin: One of my favorite exercises is what we call “The Dream Big, Start Small” activity. It’s about encouraging people to think big but start with manageable steps. We ask readers to envision something huge they’d love to accomplish and then break it down into smaller, actionable steps they can start immediately. It’s a way to keep the dream alive without feeling overwhelmed.

Sam Seidel: Another exercise is called “Asset Mapping,” where readers list out all the skills, resources, and connections they already have at their disposal. Sometimes people don’t realize how much they have to work with until they put it on paper. This exercise helps people see their strengths and resources, so they can start building momentum with what they already have.

Tom Vander Ark: Those sound like incredibly useful tools. I can see how mapping out assets and starting small could make big dreams feel more achievable. What’s one piece of advice you’d give to someone who feels stuck or unsure about their path?

Olatunde Sobomehin: I’d say, don’t wait for permission. A lot of times, people feel like they need approval or the right circumstances to start something. But you don’t need to wait. Start where you are with what you have. Take small steps, and let your passion drive you. Every step forward will bring clarity and open up new opportunities.

Sam Seidel: I agree with that wholeheartedly. And I’d add that it’s okay to pivot. Sometimes you start down one path, and it doesn’t feel right, or it doesn’t go as planned. Don’t be afraid to adjust. Creative Hustle is about flexibility and resilience as much as it is about ambition. Be open to new directions and trust the process.

Tom Vander Ark: Such great advice. It’s clear that Creative Hustle isn’t just a book about achieving success—it’s a guide to finding fulfillment on your own terms. Thank you, Olatunde and Sam, for sharing your insights and for the inspiring work you’re doing. I know our listeners will find a lot of value in this conversation and in your book.

Olatunde Sobomehin: Thank you, Tom. It’s been a pleasure talking with you.

Sam Seidel: Thanks so much, Tom. We’re grateful for the chance to share.

Tom Vander Ark: And thanks to all our listeners for tuning in. You can find Creative Hustle: Blaze Your Own Path and Make Work That Matters wherever books are sold. We’ll also include links in the show notes. Until next time, keep learning, keep innovating, and keep making a difference.

Links:

• Sam Seidel Twitter
• Sam Seidel LinkedIn
• Sam Seidel Bio
• Olatunde Sobomehin LinkedIn
• Olatunde – Praxis Labs
• Olatunde Sobomehin Twitter
• Creative Hustle: Blaze Your Own Path and Make Work That Matters
• HipHopGenius.org
• StreetCode Academy
• Sam Seidel on Design Thinking
• Sarah Stein Greenberg Podcast
• Design for Belonging by Dr. Susie Wise
• New Pathways
• Rep Mag
• High School for the Recording Arts
• Big Picture Learning