He's thinking specifically about the issue in what I think is perhaps the toughest context: government. His point is that "government must be granted the license to fail ... so it can have the courage to innovate," and surely that's right in theory.
But it's probably tougher to tolerate failure in government than elsewhere because it is by definition pluralistic and needs to meet some consistent standard. Stakeholders are bound to question why their programs are always the ones that seem to fail.
In private life – business and commerce, the academy, creative endeavors – Jeff's point is fundamentally applicable. I was lucky enough to be taught as a young editor periodically to ask the folks I worked with, "When was the last time you made a good mistake?"
I'd stress, of course, that a "good mistake" didn't involve coming in drunk and misspelling all the names. A good mistake was one where we learned something we couldn't have learned otherwise, where we were better off afterward for what we learned, where we had a clearer vision of what to try next.
The real reason to ask them, though, was this: If a person can't think of a good mistake, that means he's been asleep. It's axiomatic that people who try new things will fail; the only people who don't aren't trying.
Jeff also cites Craig Newsmark's observation that England suffers widespread "failurephobia":
I was struck by the repeated comment that failure is stigmatized in UK business culture. In Silicon Valley, failure is just a normal phase of one’s career. You might succeed in your first endeavor, probably not, so you’re ready to persist in subsequent efforts…..
So true. I lived in England for a year in the early 90s, a period of widespread despair and discouragement for the Brits. I wrote an essay about feeling "suffocated" by the culture there. As an English columnist wrote in noting his countrymen's widespread criticism of Bill Clinton's inauguration, "Every public ceremony in England is ancestor worship; every public ceremony in the United States is a fertility rite."
Think about this also calls to mind the supposed motto of the French bureaucracy: "Nothing should ever be done for the first time."
The U.S. has a huge advantage over "old Europe" in these matters – but not, I think, over India, or China, or Brazil. Beware.