"People like to pigeonhole and say, Well, I'm a Washington insider, and you know, that's quite silly. What does that even mean?"

This quote by Bob Woodward is referring to the propensity of individuals to classify and label themselves and others. He is suggesting that this practice is "silly" and that it is not a meaningful method to specify oneself. He is suggesting that the term "Washington expert" is an oversimplification and does not precisely describe the complexity of the individual. He is suggesting that it is more important to focus on the individual's skills, experiences, and accomplishments instead of a label. He is likewise suggesting that labels can be restricting and can avoid individuals from seeing the complete capacity of an individual. Eventually, Woodward is recommending that labels must not be used to define individuals which it is more crucial to focus on the individual's special qualities.