This article is based on a keynote presentation at an international conference where the focus was cross-over career guidance. Simon and Garfunkel's popular song, "Bridge over troubled water", was used as a metaphor for exploring the cross-over theme. Some of the concepts under consideration included the working alliance, the importance of a keystone, qualitative and quantitative guidance methods, working from the past and the future, and building connections. There also was the suggestion that other metaphors could be used as a way to broaden the exploration.