Complex sentence: After graduating from high school, he lived in New York and then for eight years in Chicago, where he worked as a delivery salesman for Coca Cola, for UPS, for a furniture store, and for Union Pacific Railroad.
Split into simpler sentences: After graduating from high school, he lived in New York and then for 8 years in Chicago. In Chicago, he worked as a delivery salesman for Coca Cola, for UPS, for a furniture store and for Union Pacific Railroad.