Mindy Kaling's book "Why Not Me?" explores the complexities of entitlement, particularly in the context of personal achievement. She reflects on the idea that feeling entitled can make a person difficult to tolerate, highlighting how this trait is often viewed negatively by others. Kaling recognizes that entitled individuals can be seen as insufferable, especially when they do not pair their sense of entitlement with effort or accomplishments.

However, she distinguishes that if someone with a sense of entitlement also puts in hard work, their behavior may still be seen as annoying, but it is more justifiable. Kaling’s candid observations showcase the balance between feeling deserving of success while acknowledging the importance of hard work, ultimately emphasizing that a combination of both can create a challenging but authentic personality.