Sixty-Something: Happy New Year Starting Over In The Hamptons

Every year the world celebrates the coming of the New Year. With every New Year comes change. Sometimes we choose to change, other times other people make decisions that bring change to our lives. Many times the change may mean starting over. Change can happen via one’s relationship, career, or even health situations, or in the case of sixty-something folks’ retirement due to age realities.

The East End of Long Island is unique as a landing spot for a soft landing for many who are starting over. I know I never planned on coming to the East End to start over. I sort of landed on the shores of the East End on a sailboat I just bought, and never really went back to my NYC life. It wasn’t the plan; it was just how it played out. Amazingly, so far, seventeen years later it has worked out very well. Sadly, I have seen situations where for others it has not. However, mostly I believe it does end well when one comes to live permanently on the East End going back to those Lynn, Massachusetts folks of 1640 who also came by sailboat and landed at Conscience Point in Southampton. They took great risks and must have had great doubts, especially during their first winters. We can only imagine what they felt their first New Year’s Day on the East End. I remember mine.

I was invited to Gurney’s to cover the event for the now defunct Montauk Pioneer by Gurney’s social director Ingrid Lemme and CEO Paul Monte, as were perhaps ten other members of the East End press. Back then there were only a handful of reporters since it was just before all the creation of the “news websites” that now exist both independently and as parts of the East End papers. East End media is a tight group, only back then there was just less of it.

It was a lavish gala with the crème de la crème of winter Montauk Society. Lots of tuxedos – even I somehow had one on too. Even though I was given a plus one I attended alone, but Ingrid sat me next to a few other singles at a media table and we talked shop. I remember being one of the last to go and having the DJ close the night with Frank Sinatra’s In the Wee Small Hours of the Morning, a song that delighted Paul Monte, a fellow Italian.

It’s not easy to start a life over brick by brick in a new place, but the Hamptons being such a beautiful place makes it easier. If you are respectful to the social norms of the locals it makes it easier. Although it can be expensive with local help there are deals and good housing situations. It you have lots of money I suppose it gets easier, but my starting over was not well financed. A divorce, a tumultuous end to a long successful family business with assets tied up in real estate that took over ten years to sort out had me living paycheck to paycheck from writing, delivering papers, working as a bar doorman, being a substitute teacher, and delivering flowers. For a short while I was doing all those things at the same time! It was crazy literally going from one job to another and sleeping but a few hours a day. It was hard, it was tough, and looking back it may have been the best period of my life, except perhaps when my children were young and growing up. The crazy schedule put me into an orbit to where I met my wife. That too was a starting over. A starting over that’s been wonderful. Happy 2020 and if you are planning on starting over somehow in the Hamptons, best of luck!