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The S.B. Questionnaire: Joel Weiss

Talking Education and Opportunity with the Head of School at Crane Country Day School

Joel Weiss Head of School at Crane School | Credit: Paul Wellman

“If you combine strong academics with a creative bent, the world is your oyster,” says Joel Weiss, the buoyantly enthusiastic “Head of School” at Crane Country Day School, which was founded in Montecito in 1928. “It’s really important to get a big powerful dose of rigorous academics coupled with unbridled creativity.”  

Crane is dedicated to providing experiential, hands-on activities to round out the education of its students, who range from kindergarten to eighth grade. Joel has been the Head of School since 1999, nearly 20 years now. “It’s snuck up on me,” he confesses. “It’s been a lovely experience. I’m realizing that this is my life’s work. I love this, and what I’ve done.”

It was also the start of another important chapter of his life: parenthood. When Joel was hired, he and his wife, Mary Anne, had just had their first child. “He was only 3 months old,” said Joel. “I’ve had this rare thing where both my children grew up and attended my place of employment. I got to see them all the time.”

In person, Joel is delightful and leans forward as you converse with him. Our meeting was supposed to take an hour, but turned into a two-hour conversation filled with enjoyable tangents. He is very expressive, using his hands fervently as he speaks.  

He and Mary Anne reside on campus. “I live in the company store,” he tells me laughing, explaining that Crane is always full of lovely people and wonderful opportunities. “People, from staff, parents, and students are there, and they want to participate in something bigger than themselves.”

Joel was born in Manhattan. His dad came from a poor Jewish background, but became a lawyer, built a prosperous career, and moved the family to Westchester County. Joel fondly recalls being awakened by his dad in the middle of the night to watch movies like On The Waterfront playing on TV. “This is an integral part of your education,” his dad would say.   

Joel attended Horace Greeley High School in Chappaqua, New York, and intended to take engineering in college to become a patent lawyer.  He chose Swarthmore College and then experienced a huge awakening. “Most of the people I knew were conventional,” he acknowledges. “Now my roommate in college was from Nigeria. It was a cognitive shift for me. I started meeting people whose passions were not connected to profitable directions.”  

During his sophomore year, Joel took an elective called Intro to Education. “It was a light switch for me,” he says. “They made us go into town and do an internship teaching fourth grade. The teachers at the education classes were so different.”

He singles out one particular mentor: Bob Gross. “He cared about us, and about forging a sense of community,” says Joel, who ditched the engineering plan. “I remember calling my dad and telling him I’m thinking of ditching engineering for education.” His dad replied, “That’s your life decision.”

Joel graduated in 1982 with a degree in education and psychology. Bob Gross also encouraged him to go to Harvard School of Education. “He literally handed me an application,” recalls Joel, who opted for an intensive program. “I was the only person who came directly from college.” His colleagues were older with much more work experience. “All the assignments were project-based,” he says. “It was the first time I had that experience.”

After graduating in the early 1980s, he was hired at Lick-Wilmerding High School in San Francisco.  “I stumbled into that job,” he admits. “Funny name, awesome school.” The school had just received a $100,000 grant to start a computer program, and Joel had two years of computer programming under his belt thanks to Swarthmore. “That was my first job out of school,” he recollects. “I wanted to be in California and San Francisco, but, most importantly, I wanted to help form, help create.”

Eventually, he drifted into administration, and he was asked to be the dean. “I was in charge of student council, school trips, and in charge of discipline,” he says. “I loved it. It was a tremendous opportunity for growth, a learning opportunity. You had to handle discipline with compassion. I love dealing with troublemakers. I love being able to help them. To this day they credit me for being such an influence in their lives.”

In 1995, the head of school went on sabbatical and Joel was asked to become the acting head.

“I didn’t know what I was getting myself into,” he confesses. “I knew the teaching side of the equation. But not fundraising, nor running a board and finances. Being the boss you get involved in strange, unpredictable things. I had lunch with Rosa Parks that semester! That was my first time being the top boss. It was overwhelming and it was heady.”

In 1996, he became the head of the middle school at San Francisco Day School. Then, once again, the head of school went on a sabbatical and Joel had to step up. That means he’d gotten “two shots at bat” before becoming the Head of School at Crane , which is rare in this line of work. Prior to his hiring, the school had experienced a revolving cycle of leadership. Joel has stopped that. “I love my job,” he tells me with a warm, genuine, big smile.

Joel Weiss answers the Proust Questionnaire.

Who makes you laugh the most?That’s one of the reasons I’ve stayed at my job so long: kids are funny! Everyday I hear wacky things from students and it makes me laugh and love my job.

What is your motto?There’s this one Margaret Meade quote that I often turn to in times of trouble: “We are continually faced with great opportunities which are brilliantly disguised as unsolvable problems.”

What do you like most about your job? My students! I teach, I get to be creative, I problem-solve, I get to write, and I’m constantly meeting new people.

What is your idea of perfect happiness? A challenging early morning hike up Romero Canyon.

What is your greatest fear? Losing my inherent optimism.

Who do you most admire? Vincent van Gogh. He was so ahead of his time. During his life he didn’t get much praise, and still, he pushed himself forward to produce these powerful works of art that command attention.

What is your greatest extravagance? Sending my kids to the very best schools. Places where they are safe and surrounded by interesting people and being pushed intellectually and having fun. What a luxury for a parent!

What is your current state of mind? I’m still in love with California! I grew up in New York, but for the last 36 years, it’s been my home and I can’t imagine living anywhere else.

What is the quality you most like in people? I love being with people who consistently smile and have an inner light — being with them is fun and quirky and my own energy is elevated.

What is the quality you most dislike in people? In my job, I do my best to connect with others, to really listen, and to always look for the good. It’s uncommon, but some people are constant complainers and that can be exhausting.

What do you most value in friends? I value old friends, the type where you can just pick up where you left off, there is no guilt or pause or hesitation, just fun.

What is your most marked characteristic? Two things come to mind: I talk with my hands, and I don’t sleep very much.

Which words or phrases do you most overuse? When I’m talking about my school, it isn’t long before I say the word “community.”

Which talent would you most like to have? I would love to be a singer, but I have a terrible voice. Those few times when I do sing, I struggle to stay on tune, I have terrible rhythm, and I even stumble remembering lyrics. Luckily my wife likes my singing.

If you could change one thing about yourself, what would it be? I’m in my late 50s and my metabolism has definitely slowed down, so I miss the old days when I was an eating machine, I had an endless appetite, and didn’t have to think about taking care of myself.

What do you consider your greatest achievement? It is corny, but it would have to be my relationship with my kids. I love them so much and they are great people and fun to hang with. Mary Anne and I loved parenting, having dinner together every night, reading the kids to sleep, and hosting huge birthday parties — it was such a high point in my life.

Where would you most like to live?When I retire, my wife wants us to live in a caucus state, like Iowa, during an election year. But for me, I’d love to live in Japan. We have traveled there a few times and I’m drawn to the food and the culture, and it is just fun to be in such an orderly society.

What is your most treasured possession?My anvil. I found it on Craigslist and drove all the way to the Bay Area to get it.

Which historical figure do you most identify with? I’m an educator and I’ve always felt a connection to John Dewey. He believed in kind, loving schools that tended to the emotional needs of children.

On what occasion do you lie?I regularly visit with my 91-year old dad in Pasadena. He is still pretty sharp, but he often repeats the same stories, and I’ll pretend I’m hearing them for the very first time.

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