Speaking of people who are great at writing, Clay Shirky’s post on the failure of Healthcare.gov is spot-on.
I could blockquote the whole thing, but here’s just a few nuggets I loved:

It’s certainly true that Federal IT is chronically challenged by its own processes. But the biggest problem with Healthcare.gov was not timeline or budget. The biggest problem was that the site did not work, and the administration decided to launch it anyway.
And:
The idea that “failure is not an option” is a fantasy version of how non-engineers should motivate engineers. That sentiment was invented by a screenwriter, riffing on an after-the-fact observation about Apollo 13; no one said it at the time. (If you ever say it, wash your mouth out with soap. If anyone ever says it to you, run.) Even NASA’s vaunted moonshot, so often referred to as the best of government innovation, tested with dozens of unmanned missions first, several of which failed outright.

Failure is always an option. Engineers work as hard as they do because they understand the risk of failure. And for anything it might have meant in its screenplay version, here that sentiment means the opposite; the unnamed executives were saying “Addressing the possibility of failure is not an option.”
And one more:
An effective test is an exercise in humility; it’s only useful in a culture where desirability is not confused with likelihood.
The launch of Healthcare.gov has been an embarrassing mess.