Anthony Tomassini ’70 said he would have laughed if while he was at Yale, someone had told him he would one day have one of the most important music-critiquing jobs in the United States.

Tomassini, the chief classical music critic at The New York Times, discussed his life and work before more than 80 students and faculty members at a Saybrook College Master’s Tea on Wednesday, which was co-sponsored by the Yale Symphony Orchestra. Tomassini said he has encountered a number of challenges, particularly before settling in his current position, and he owes much of his success to a flexible attitude that allowed him to overcome setbacks.

Though his original ambition was to become a teacher — a profession that would balance his love of performing and imparting musical knowledge to others — Tomassini said that finding a teaching position during the 1970s was difficult and that he worked instead as a restaurant waiter for four years.

“I can still clear a whole table on one arm” he said.

After waiting tables, Tomassini landed a teaching position at Emerson University, only to be denied tenure and forced to find other work. Though the experience was crushing at the time, he said, in retrospect it was probably the best thing that ever happened in his life.

Since he had always enjoyed writing, he took a position as a free-lance writer at The Boston Globe. There, he worked closely with composer Virgil Thompson, who Tomassini said was one of the most influential people in his career. But after being denied a staff reporter position, Tomassini moved to New York, in what he said was an extremely risky but liberating experience. He became a staff reporter for The New York Times in 1997 and rose to chief critic by 2000.

Tomassini said he believes there is an important moral to his story.

“When you’re young, knowing what you want to do can be a good quality,” he said. “On the other hand, you can’t be so fixed that you fail to see opportunities when they present themselves.”

Though he has been primarily involved in journalism, Tomassini said he thinks he has, to some extent, accomplished his original goal of becoming a teacher.

“I always wanted to be a teacher, and I feel like a teacher even today,” he said. “I champion ideas and bring things to people’s attention that otherwise might have been overlooked. It’s even better though, because unlike in a class where some people don’t want to be there, everyone who reads my column actually wants to read it.”

Tomassini said the hardest part of his job is to write effectively for all of his readers. He said while some readers know absolutely nothing about music, others are experts.

Students said that they enjoyed the discussion because it provided interesting insight into Tomassini’s life.

“I really liked how he gave us a good look into his personality,” Kara Weisman ’09 said. “It’s always interesting to get to know someone by seeing how they talk about themselves.”

Other students said they wished Tomassini had spoken more specifically about his work and the writing profession.

“I’m really interested in journalism and different writing styles,” Nicole Villeneuve ’09 said. “It would have been nice to hear more about ways in which to write about music and how to get involved in something like that.”