Boston is proof that good intentions don’t always get built. The city’s housing crisis is no secret, but efforts to add density keep colliding with layers of regulation and fierce neighborhood opposition. This is the paradox of American urban planning: we say we want affordability, yet fight the very tools that deliver it. In Boston, this manifests as zoning battles, design delays, and endless public hearings. The result? More pressure on prices and more people priced out. The opportunity is clear—denser housing in walkable areas—but the politics are stubborn. Watching Boston wrestle with its own future is a reminder that housing reform isn’t just technical, it’s cultural. Until we address the fear of change, density will stay stuck in neutral.