Since "the only constant is change," as Taylor likes to say, he changed course again when he realized that entertaining kids was his true calling.
"At first I thought everyone could improvise and write songs the way I could," he said. "But I soon understood that I could have a great impact on children's lives."
His pursuit of a career as a teaching artist was bolstered in 1981 when he became associated with the Wolf Trap Foundation for the Performing Arts. He still maintains a relationship with the Virginia-based foundation's early learning institute.
"Wolf Trap taught me how to market myself," and the makeover into Kinderman followed four years later, he said.
That early success led Taylor, who never married, to decide to purchase a house in Owen Brown, where he still resides.
And as part of his evolving act, he hired Dillon Clarke as Kindertwin, singing harmony and accompanying Taylor on the keyboard among other duties. The fourth in a succession of like-named assistants, Clarke has been part of the act for 14 years.
Mimi Flaherty Willis, Wolf Trap's senior director of education, says Taylor is "one of the country's most generous and genuine performers."
She acknowledged that he has a knack for grabbing audience members and thoroughly entertaining them with his unique energy, but adds there's "something else" going on.
"He is theirs; he belongs to them and they know it," she said, an observation she's developed over her 20 years of working with Kinderman and seeing the intimate rapport he has with audiences.
"He didn't go off to New York, though he could have," Flaherty Willis said. "He's one of those working artists who has made a commitment to his community and stayed put."
In looking back over his long and varied career, Taylor said one universal truth has emerged.
"Kids need to know you love them and then they learn to love others," he said. "That's a skill we all need."