Live the dream Definition 1 of 1Pro Tip 1/3Positive Connotation The phrase often implies happiness and fulfillment from achieving personal goals. She finally became a pilot and is living the dream. Pro Tip 2/3Idiomatic Usage Used metaphorically and should not be taken literally; it's about a feeling of success. By traveling the world with his music, he's living the dream. Pro Tip 3/3Cultural Aspirations Can reference common cultural goals like wealth or career success. She got to Hollywood and is living the American dream.