Complex sentence: While an undergraduate, he bet a fellow student that he could travel around the world without money, and after a year of teaching, proceeded to do so when he spent sixteen months circling the globe, working to earn money along the way.
Split into simpler sentences: While an undergraduate, he bet a fellow student that he could travel around the world without money, and after a year of teaching, proceeded to do so. He spent sixteen months circling the globe, working to earn money along the way.