From mainframes and virtualization to containers and generative AI, every transformative technology follows the exact same trajectory: initial euphoria, peak skepticism, and eventual practical reality. At Cloud Field Day, host Alastair Cooke catches up with longtime collaborator Chris Williams to reflect on his 11-year journey guiding vBrownBag through the industry's fastest-moving shifts. Chris breaks down how technologists can surf the edge of emerging tech without falling into doom-and-gloom or blind optimism, why hands-on practitioners provide the most authentic education, and the career-changing power of giving grassroots engineers a platform to share what they build.