Island Profile: A turn in the road 20 years ago leads to an MBA and a career

Lynn Kay Winters grew up in the Richmond Hill section of Queens, the first in 11 generations of her family to be brought up off Shelter Island. As deep as her family roots may be, it took her a while to plant her own roots to keep her here for long.

“My mother and father both grew up here,” she said. “My father’s side are the Dickersons, Havens and Sylvesters and my mom’s family were Dutch immigrants. But the two of them, my parents, June Martin and Bob Smith, I don’t think they could wait to get off Shelter Island.”

“I think it was the day after high school” for her in 1959, a few years after him, that they bee-lined it into the city … to the big exciting world.”

In the years to come, Lynn Kay couldn’t wait to return.

Her parents lived in Manhattan at first, then moved to Queens where she was born. After her parents split up two years later, she went back and forth between her mom’s home in Queens and her dad’s in Northport and then Levittown, but always summered on the Island, where both grandmothers were, as well as other relatives including “at least a hundred cousins.”

“When people say to me, ‘Where are you from?’ I almost always say, ‘Shelter Island,’ because this is the place that always felt most like home,” she said during a recent chat at her Penny’s Path home.

Asked if she could draw a family tree, she laughed. She said she couldn’t imagine a piece of paper big enough.

“When we were growing up, Helen Smith, my grandmother, was the town clerk, and Dottie [Ogar], her daughter, was her deputy,” said Ms. Winters. “Dottie is my father’s sister, and we did most weekends here. Sharon Jacobs is my first cousin, she’s Dot’s deputy now. Sharon and I played on the steps of the Town Hall,” where the Town Police are now headquartered, “and my favorite part was to watch people come in and get their beach stickers.”

“I remember the smell of that Town Hall … I can see those steps clear as day,” she said.

When she was in junior high school in Queens, her father moved with his second wife Marge to Tilden, Nebraska, a town of 950 people where Marge had been born and raised. Marge owned a farm that was four miles out of town. Lynn Kay eventually joined them and went to high school in Tilden for two years. “They thought I was from outer space,” she said of the local kids. “I was wearing high heels with my jeans. If you remember 1980, you remember Jordache jeans and all that.” The way she and her friends back home in Queens dressed “we thought we were so fabulous.” she said, but “we looked like a bunch of tarts” to the Nebraskans.

She gives her three parents — father, mother and stepmother — a lot of credit for her happy childhood. “There was no handbook for how to do it then, so I’m particularly proud of all three of them. I was probably in my 20s before I realized that divorced people don’t necessarily like each other.”

Her father raised a second family so Lynn Kay has a much younger half-brother and half-sister. “I missed them when they were very little, when I was far away. They were going to pre-school and kindergarten when I was in high school. You can’t be in two places at one time, although I’ve done a pretty good job of it throughout my life, and I think that’s why Shelter Island appealed to me so much. It was always the place to come back to, with plenty of relatives.”

In 1982, just turning 18 in the summer before her freshman year at Queens College, she was to begin a pattern that lasted for a number of years — waitressing and bartending on Shelter Island in the summer and returning to school in the fall. That first summer, she was at the Chequit. “We figured out that if you ran the tub in room 5, and the bar sink was on, you didn’t get any water, and if the air conditioning was on in the dining room, you couldn’t turn the lights on in the snack bar. There were all these funky things that I’m sure James [Eklund] has fixed but those were the things that I loved about it, that it was so quirky.”

She left school after three years and continued waitressing and bartending in Queens during the winter and here during the summer. Eventually, she was able to limit her work to six months and she spent the rest of the year traveling.

“The restaurant bug bit me and it was very good money and an awful lot of fun,” she said.

She worked at every restaurant on the Island, she thinks, at one time or another, including the Dory, the Yacht Club and the Ram’s Head. When she wanted to ski, she found work in Vermont, where she stayed for several years. During her travel months, she worked on an Israeli kibbutz, and also went to Egypt, Turkey and Greece, among other places.

“Somewhere along the line I worked in the Bahamas as a stewardess on a yacht but I can’t figure out what year that was,” she said.

In 1989, she came back to visit in the spring and stayed with Dick Edwards, the owner of the Dory. She was “in tears on his deck at the thought of leaving” Shelter Island again, she said, so she went back to Vermont to quit her job there and bring back “all my stuff in a UHaul.”

But before she could get settled here again, she was offered a short-term job in the Caribbean and she took it.

By 1990, she was living in Southold with a significant other and working in restaurants on the North Fork. Then in 1991, she answered an ad for the position of receptionist in a physician’s office in Riverhead and was hired. That was 20 years ago, and it was a turning point in her life. Her boss encouraged her to go back to school and she got her degree by taking an online program through Empire State College in 1993. She was promoted to a management position and went on to get an M.B.A. in 1999 in medical group management through an online program at St. Thomas University in Minneapolis. By then, she was the manager of a large and still growing medical office.

Managing a medical practice “is getting more complicated all the time, by the second,” she said. “I’m not sure any other specialty would have gripped me like this one did, and oncology is not for everyone but I absolutely love what I do. We just got back from vacation and I couldn’t wait to get back to work.”

The practice she manages, Eastern Long Island Hematology/Oncology P.C., involves three physicians, four nurse practitioners and a staff of 40 with offices in Riverhead and Southampton, where she now works and lived from 1998 to 2003.

In 2001, she married Bix Winters, a first marriage for her, a second for him. They had met in a Riverhead restaurant, the Birchwood, where Lynn Kay was a patron and Bix was the bartender.

3Bix was born in California and lived in Europe, in England, Spain and Germany, moving often because his father was a musician in Glenn Miller’s band. He returned to the States when he was in his late teens. He’s never lived anywhere longer than the eight years he’s spent with Lynn Kay in their current home on Penny’s Lane in Shelter Island, which they bought in 2003.

“There’s something very appealing about it for him,” Lynn Kay said. He still works in restaurant management, overseeing the Pridwin restaurant for the past two years.

Lynn Kay is happy at work and at home, surrounded by friends and relatives, a member of the DAR, a 5K and 10K runner and a stepmother to Bix’s two daughters, Leah and Alyse, now in their mid-20s. One senses a deep and real satisfaction — probably best summarized in three small but very large words — “home at last.”