Crazy as this might seem, there’s a long tradition of using courageous questions to get us out of our tidy conversational habits. One list of questions was made famous by the novelist Marcel Proust, including ‘What is your most treasured possession?’; ‘What is the trait you most deplore in yourself?’; ‘What is your favourite journey?’; and ‘How would you like to die?’ All of these questions beat ‘What do you do for a living?’
