Tucked into the far end of the main office, principal’s assistant Carolyn Benfield meticulously sketches a sugar skull onto a whiteboard to celebrate Day of the Dead as she writes out Principal Adam Paulson’s agenda. 

The details and small touches are what have cemented Benfield’s legacy at Palo Alto High School after serving as principal’s assistant for the past 20 years.

Benfield will retire in December.

“It’s all very surreal to me,” Benfield said. “I get that now I’ve come full circle, but I love this place. I really do.”

Benfield explained that her nebulous job description was best described by former Principal Scott Lawrence.

“He used to say to me that my job is ‘other tasks as assigned,” Benfield said. “It could be calling animal control because there’s this wounded bird on the Quad, it could be helping put on a breakfast, [or] it could be taking notes in a meeting — your more standard secretarial stuff.”

In her time at Paly, Benfield worked for Principals Cook, Pearson, Dryer, Laurence, McEvoy, Winston, Diorio and Paulson. According to Benfield, the biggest change in Paly’s evolution was the doubling of its student population.

“You wouldn’t think that [physical change] would have an effect on the culture, … yet it does,” Benfield said. “The student population was small enough that you fit all four classes in this amphitheater that had a stage up front, so the physical changes in the campus make a big difference.”

Benfield also recalled how she has seen multiple generations of students walk through Paly’s doors.

“One of my students that was here my first couple years was in the other day visiting and his son is starting here next year,” Benfield said. “I’ve now come full circle.”

Benfield said she looks back on her time at Paly with a sense of nostalgia and happiness. Some of her best memories have come from her interactions with the vibrant community around her.

“After 20 years, it would be nearly impossible to pick out one special [memory], but I can tell you that any of the best moments always involve the students,” Benfield said.

Before working at Paly, Benfield owned a house cleaning service and managed a hotel and restaurant in Sonoma. She is still unsure of what she plans to do after retiring, but hopes to spend more time with her family, including a grandson entering high school next year, and take up hobbies like gardening.

“I understand that exercise is good for you, so I’m going to try that theory out,” Benfield joked. 

She cites a positive mindset as imperative to her success on the job.

“Assume always good intentions from students, from parents, from co-workers,” Benfield said. “Just always assume that they’re coming to you with a good heart and react and respond that way.”

According to Benfield, there are both internal and external candidates interviewing for her position, and the next principal’s assistant is set to be chosen sometime this week. 

Benfield offered her advice for the person that will fill her shoes.

“Keep your sense of humor, be kind and expect the unexpected, but mostly just treasure the time,” Benfield said.