In August 2012, Knight Capital Group pushed a routine software update to its automated trading system.

Seven servers were updated. One was not.

In 45 minutes, the company lost $440 million.

No cyberattack. No sabotage. No dramatic villain.

Just a missing update, an untested rollback, and automation moving faster than humans could react.

Healthcare.gov is often remembered as a broken website. In this episode of Project Management Is Boring, we unpack why that story misses the point. The failure wasn’t caused by bad developers or an impossible deadline — it was the result of fragmented ownership, unclear authority, ignored integration risk, and a leadership structure that made honest reporting nearly impossible.

This episode walks through how dozens of vendors, competing agencies, and “green” status reports combined to hide real problems until launch day, when the entire system collapsed in public. More importantly, it shows why Healthcare.gov isn’t a one-off disaster — it’s a textbook example of how normal, everyday project management decisions quietly create catastrophic outcomes. If you’ve ever worked on a project that felt fine right up until it suddenly wasn’t, this story will feel uncomfortably familiar.

In this episode of the Project Management is Boring podcast, we explore why refusing requests is one of the most powerful skills a project manager can have. Projects always run within boundaries—time, budget, scope, and resources—and saying yes to everything undermines those limits.

We look at why saying no feels uncomfortable and how to do it effectively, using strategies grounded in logic and real-world examples. By learning to set clear boundaries, prioritize what truly matters, and communicate decisions confidently, project managers can protect their teams, reduce burnout, and keep projects on track.

Saying no isn’t rejection—it’s essential project discipline.