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I would agree. I would suggest that people who are skilled, and good at what they do did not get to that state without making mistakes that could fall into the categories described in the article as stupid. The trick is, as you say, to determine why said mistakes occured, and importantly to avoid making the same stupid mistakes in the future.

The best practitioners of "insert discipline here" are those that have made all the (survivable) mistakes.

I guess the difference is how you handle the risk of failure. Dismiss it because you think you won't fail, or prepare for it because you're aware you might?

Depends on what you call enlightenment. In the zen/taoist sense, it actually results from _dropping_ your expectations, ie. just do your stuff.