In this episode of Practice Disrupted, Evelyn Lee speaks with Henry Gao, architect turned digital creator, educator, and founder of Draw With Gao, a platform that teaches architects and designers how to leverage iPad sketching as both a creative outlet and a new revenue stream. Henry’s path offers a rare glimpse into how an architectural background can evolve beyond the profession into entrepreneurship, storytelling, and scalable creative business.

Henry shares his journey from sketching historical buildings as a child in China to navigating a traditional architecture education in Canada and the U.S., and eventually stepping away from firm life after realizing it didn’t align with his values. Along the way, he experimented with freelance renderings, ran an Etsy shop, studied architectural photography, and slowly built an ecosystem of content that now supports a global audience of designers.

Together, Evelyn and Henry explore the challenges of leaving the traditional architecture path, the role of mentors and paid coaching, and what it takes to build a sustainable business around content, courses, and community. They also discuss Henry’s evolution from side hustles to a full-time educational platform, the power of standard operating procedures (SOPs), and why he believes teaching is a form of service that architects are well-equipped to offer.

“When I stopped trying to fit into traditional architecture roles, I started to see all the ways my training could serve people. Teaching, drawing, storytelling, those are still architectural skills. But now I use them to empower others, and in doing so, I’ve built a business that’s both creative and sustainable.”

- Henry Gao

The episode concludes with a reflection on ikigai - the Japanese concept of purpose, and how Henry’s work sits at the intersection of what he loves, what he’s good at, what people need, and what can be monetized. It’s a conversation about reimagining the future of architecture as something broader than buildings - something designed to fit the life you want to live.

Henry Gao is a designer, educator, and the founder of Draw With Gao, an online platform offering courses, tools, and coaching for architects and creatives interested in mastering digital hand drawing. Trained in architecture at Carleton University and Cornell, Henry transitioned from working in design firms to building a business rooted in teaching and storytelling. His work focuses on helping creatives turn their skills into impactful, scalable offerings in the creator economy.

This episode is for you if:

✅ You’re an architect curious about alternative career paths

✅ You want to learn how to monetize creative skills beyond the billable hour

✅ You’ve considered launching an online course, product, or content platform

✅ You’re exploring ways to build freedom and sustainability into your design career

What have you done to take action lately? Share your reflections with us on social and join the conversation.

📍 Show Links:

• Connect with Henry on LinkedIn
• Follow Henry on Instagram
• Learn more about Draw with Gao
• Subscribe to Henry’s Youtube Channel

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