By the mid 1970s, his career had stalled. In an attempted comeback Los Angeles music publisher/songwriter Richard D. Kaye, acting as Tim's manager in 1976, arranged studio time for Tim to record the album Unfinished Song featuring seven new Rose compositions and the title track "Unfinished Song" written by Kaye. He recorded The Gambler in 1977, with a group that included guitarist Andy Summers, only to find that the record company refused to release it. He returned to New York for a number of years, living in Hell's Kitchen on Restaurant Row, and then much later Lincoln Square near Central Park. Having lost his contacts in the music industry, he was forced to work as a construction laborer until an opportunity arose to sing jingles for TV commercials in early 1980. Rose sang on many jingles, including Big Red gum and Wrangler Jeans, and voiced ads for the Big Apple Circus. This work funded his much-delayed college education, which he began at the age of 40. Rose graduated in 1984 from Fordham University at Lincoln Center in Manhattan, with a degree in history. He became a Wall Street stockbroker and a teacher, got married, and eventually divorced. While working on Wall Street, he met Dennis Lepri, former lead guitarist for the folk rock group, Gunhill Road. They became friends and together collaborated on new material, performing in clubs throughout New York. After the 1987 stock market crash, the two parted ways and Tim got out of the business. He continued writing and performing at select venues, such as The Bitter End. He also battled with alcoholism.