Can you be “too confident”? How entitled is too entitled? In this third of a series of Happy High Status takeover episodes, Viv talks to broadcaster and journalist James O’Brien, LBC presenter and author of How They Broke Britain (coming in Nov 2023), about challenging difficult and entitled people (especially certain privately-educated politicians), coming to terms with his own insecurities and finding a kind of humility after experiencing a major setback in his forties. Plus James reveals how he went from being someone who felt sick talking to people at parties to feeling comfortable in himself. Is it a good idea to put on your own “cloak of entitlement” when questioning someone who loves the sound of their own voice? What do you do when faced with people who are so confident that they’re tipping into arrogance? And how can we all listen to each other a bit better and make space for different points of view?  Viv's new book, Happy High Status: How to Be Effortlessly Confident, is out now. @vivgroskop James O’Brien’s new book How They Broke Britain is out in Nov 2023.