By Barbra Shotel | It all began during my freshman year at Penn when my roommate asked me if I would go to Nantucket with her to waitress for the summer.

“Oh no, I couldn’t possibly do that,” I said. “My father would never let me.” She went to Nantucket and had a great time. I stayed in Philadelphia, and didn’t.

Not that it ruined my life or anything. In 1975, after establishing a career in television, I moved to California and landed a job as talent coordinator for The Tonight Show Starring Johnny Carson. I also taught a course at USC, explored the West and Southwest, studied Navajo weaving, took photography courses, rafted the Colorado River, quit my job at The Tonight Show, lived in New Zealand for a year, wrote articles that were published here and there, returned to California, worked in television again, went to law school at UC-Berkeley, studied in Cambridge, England, earned a law degree, returned to Philadelphia, practiced law, did oral history, and volunteered as a museum docent. Still, I couldn’t get over my decision not to waitress in Nantucket that summer in the sixties.

In spring 2000, I decided to have that college summer, nearly four decades later, on Martha’s Vineyard. It seemed like a great idea, but could I really make it happen? After all, I didn’t know anyone there. I was single again and traveling solo. I didn’t want to be there with nothing to do, and I didn’t want people to think I was a dilettante in that summer playground. I would have to find a part-time summer job and a place to live. I networked, starting with a lawyer who had family ties to the area, and by the time of my exploratory visit in April, I had three days of meetings and a place to stay (a B & B) arranged.

I drove to Woods Hole and took the ferry to the island, which was quiet in the off-season. But I met with lots of people—everyone from the manager at the Black Dog Café to Vineyard Gazette publisher Dick Reston to filmmaker Len Morris to the management of the Vineyard Playhouse.

Everyone’s first question was, “Yes, we’re hiring for the summer, but where will you live?” My competition for both jobs and housing was college kids, who live like, well, college kids—too many bodies sharing too high a rent in too small a place. I might be having my college summer, but I had limits. The good news was that real college kids leave in mid-August while I was able to stay until after Labor Day. I was a desirable hire.

The second question was, “What exactly do you want to do this summer?” I developed a mantra: “You know, I’m a lawyer. But I don’t want to be a lawyer this summer, and I’ll do just about anything—except wait tables, make beds, or clean toilets.”

I left with several job prospects and a new-found knowledge of the island’s layout, lingo, and culture. I learned that West Tisbury, Chilmark, and Aquinnah were “up-island,” and that Vineyard Haven and Oak Bluffs were “down-island,” even though any map dispels that notion. I learned that there was some snobbery about “up-islanders” not wanting to come “down-island,” and that Edgartown was considered neither “up” nor “down,” but had a cachet all its own.

A few weeks later, my summer plans gelled. I settled on a job as a house manager at the Playhouse, and rented (sight unseen) an apartment in a Victorian house in Vineyard Haven, near a small beach-front park, the Playhouse, the public tennis courts, the library, and Main Street.

On July 1st, I again took the ferry from Woods Hole, settled into my tiny apartment, and fell into a comfortable routine. Because I rotated with two other house managers at the Playhouse, I usually worked a few nights each week, which meant that I supervised the ushers, oversaw the money and cookie inventory at the refreshment counter, and played hostess to the audience. I also had to make coffee, clean the lobby tables, make sure the restrooms were clean and stocked with toilet paper, and empty the trash—which may not have been “waiting tables, making beds, or cleaning toilets,” but was pretty darn close.

Yet it was a worthwhile tradeoff. By working at the Playhouse, I met lots of people, became part of a community, and was able to structure my time. There were plenty of things to do on my nights off, either solo or with a friend—lectures, concerts, even a new-play reading by Jules Feiffer. In the mornings, I’d explore the beaches or bike the roads in West Chop or East Chop. In the afternoons, I’d walk to the post office to pick up my mail and to the library to research or write and check e-mail. Twice a week I played tennis with Francis, a French chef whom I met in a pick-up game at the public courts. In between forehands and backhands, I learned he had been with a top New York restaurant, was working on the island that summer for a wealthy New York real-estate entrepreneur, and was staying in a guest cottage on the family’s Chilmark property.

By August, the island rumor mill was in high gear, awaiting the arrival of the Clintons, the then-First Family. Hourly Secret Service sightings led to hourly rumors as to when they would arrive, where they would stay, and who they would see. I had my own rumor mill—my tennis partner, who was preparing a fundraising party for 200 guests at his employer’s estate. After Francis told me that the Clintons were invited and that the President “usually wanders into the kitchen,” I jokingly (somewhat) asked if I could help. I was hired, if that’s the right word for a volunteer.

A few days before the party, I was waiting for my toenails to dry at a salon when another customer called to say she would be late. There’s a motorcade on Main Street! The President is shopping! I was out of there faster than you can say pedicure. People lined the street five deep. All eyes were focused on the Bunch of Grapes bookstore. SWAT teams in big black SUVs watched the crowd. Then the President and Chelsea emerged. They walked down the street, shaking hands and exchanging a few sentences with every front-row person (including me). The consensus among women and men was that the President was far more handsome in person than in photographs. Of course, I felt rather smug as I would be “dining” with him, so to speak, at the upcoming party.

I arrived at the Chilmark estate days later to learn two things. First, it was not a political fundraiser. It was a 40th birthday party for the employer’s second wife and mother of his two younger children. Second, the Clintons had already left the island, and would not attend. But there were other celebrities there, including lawyer Alan Dershowitz, who wandered into “our” kitchen (a tent) looking for a cigar. He stayed for awhile and talked with some of us. (I told him I was a lawyer. Why, I still wonder, did I tell him that?)

The property was spectacular, with riding stables, a lake, walking trails, guest houses, and a comfortable family home. I was assigned to one of three kitchen teams. We were taught how to create—rapidly and in assembly-line style—the plates for each of the courses. (Think I Love Lucy without the conveyor belt.) The food was rich, gorgeous, and delicious. We were invited to eat everything too, after the courses were served.

Towards the end of the dinner, a large and beautiful birthday cake was brought into the tent. The host made a loving toast to his wife, and fireworks began lighting up the sky. It was quite a birthday celebration, and probably the most lavish one I will ever “attend.” But it was also a long afternoon and evening for the kitchen staff. I drove back down-island feeling a little disappointed that President Clinton hadn’t been there, and a little jealous that no one had celebrated my 40th that way.

Those tiny regrets faded quickly, as did my remaining time on the Vineyard. When I got home in September, everyone asked me: “So, did you meet anyone?” Of course, they didn’t mean anyone; they meant a man. I always answered: “No, thank God. After all, if I had had a romance that soured, it would have ruined my summer.”

And believe me, I wouldn’t have changed a thing about that summer.

One morning in April of last year, I opened The New York Times and saw a story about a plane crash that had taken the lives of a prominent New York City real-estate entrepreneur and his second wife as they were flying to a private boarding school in Connecticut. It was the couple who owned that fabulous Chilmark property—the couple who had everything to live for, and who had celebrated the wife’s 40th birthday in front of 200 guests and friends, their two young children, and us, the help. They would never celebrate her 45th or her 50th—or anything, ever again.

Four decades after I turned down that first summer job, life had driven home a sobering lesson: Never put off what you can do today. You might not be as lucky as I was.

Barbra Shotel CW’64 is a lawyer and freelance writer whose first article for the Gazette (“My Stint with Tonight”) appeared in March 1980, and whose most recent (an interview with Walter Isaacson on the subject of his Benjamin Franklin: An American Life) appeared in the March/April 2004 “Gazetteer” section.