So Who’s Ready for a Do-Over?

A Sag Harbor life coach helps women focus on themselves
Debra Boulanger, the Great Do-Over’s president and founder, at her company’s HQ — her Sag Harbor house — where over phone calls, video sessions, and in-person meetings she reminds her clients that it’s never too late to embark upon the quest for a more fulfilled life. Judy D’Mello

Women are givers, said Debra Boulanger, a full-time Sag Harbor resident and the president of the Great Do-Over, a life-coaching service she founded in 2013 to offer women, usually over 40, the chance for personal or professional reinvention. And that’s why, she explained, the Great Do-Over’s word for 2018 is “receive.”

“This is a benevolent world,” she said the other day, sitting in her light-filled, shabby-chic house in the village, which she admits is “overcushioned.” Women don’t have to keep giving to the point that they lose sight of their own needs, until one day they find themselves wondering, “Is this all there is?”

Ms. Boulanger should know. She was at that juncture six years ago, asking herself, as well as the health coach and personal trainer she had hired, that very question. Despite a successful career at Gartner, a Stamford, Conn., multinational information technology company, where she launched products and marketing programs that gained worldwide recognition, she felt drained and hopelessly unfulfilled. For six years she commuted week ly from North Haven, where her husband and young son were living, to Stamford, missing countless school concerts, sports games, and parent-teacher conferences. Her 25-year marriage began unraveling; the sacrifices she had made for that relationship and her career had taken their toll.

“I tuned into a source of guidance: my own internal conversation,” she said, and checked into the Insight Meditation Society in Massachusetts for a 10-day silent Buddhist retreat. It was there that she discovered the ancient tradition of Vipassana, a method of self-awareness that allows one to face everyday tensions and problems in a calm and balanced way.

In 2012, Ms. Boulanger quit her lucrative job and got divorced. During the process of her own metamorphosis, she became acutely aware of a certain order of things, those steps she took en route to transformation. “There is a process,” she said. “There’s no end point with transformation, but there is definitely a starting point.” After crafting a tangible six-step process, she said, her vision to help other women undertake the same journey became clear.

She received her holistic health coach certification in early 2013 and hung up her virtual shingle for the Great Do-Over, which she began by coaching clients privately. It soon grew to an online group program. Her client roster includes women from all over the country.

“I teach women how to listen to their gut instincts. To become aware of patterns. To recognize who they really are. And how to love themselves first. When you change inside, it shows on the outside,” she said.

The inside-outside alchemy she extols is personified on her website, where a montage of enviable snapshots show Ms. Boulanger enjoying a moment with her now college-age son, in the loving arms of a man, sipping liquids from a cup that says “Good Morning, Gorgeous.” She is her own poster child, the best possible endorsement for a do-over.

Her six-step process ferries her clients through nutritional improvements, increased mindfulness, the creation of a physical and psychological space around oneself, healing, and the eventual transformation, a journey that takes about three to six months, she said. 

Cate Cammarata, who lives in Sound Beach and teaches theater arts at Stony Brook University, hired Ms. Boulanger last year to help her launch Create Theater, an online facilitating service for the theater community.

“I’m an artist, not an entrepreneur,” said Ms. Cammarata, who is also a producer and has worked at Bay Street Theater in Sag Harbor. “I had learned all the basics about starting my business with an online coach and a mastermind group, but it was during one-on-one sessions with Deb that she helped me formulate a business plan and guided me through a blueprint of next steps. It was like having a good friend hold your hand and walk you through every step.”

The Sag Harbor life coach also helps women navigate the daunting world of dating following a divorce or the death of a spouse. Whether looking for passion in the bedroom or boardroom, the same overarching rules seem to apply, as echoed by the Great Do-Over’s tagline: “Release Fear. Think Clear. Get Into Gear.”

Kim Eagan is Ms. Boulanger’s longest-running client, having signed on to work with her in 2013, when Ms. Eagan was going through a bitter divorce.

“I first hired Deb to help me get through a really bad time,” said Ms. Eagan. “Then she helped me though the dating period, when I was ready to give up on all the online stuff. She just listened, then she’d take me step by step through the process.”

Ms. Eagan, who lives on Cape Cod and has been in a happy relationship for the last 14 months, has met her do-over guru only once in person. Currently she is in consultation with her while trying to develop a new business. 

By Ms. Boulanger’s account, the Great Do-Over is a mashup of Buddhist tenets, psychoanalysis, cognitive behavioral therapy, and the law of attraction — that 19th-century belief based on positive thinking.

“She has an unbelievable ability to manifest what it is you really want,” Ms. Eagan said.

Life coaching has soared in the past 20 years, straddling a middle zone between the work of a psychologist and a really good friend. The practice has no regulation or licensing board. Anyone can be a life coach as long as she calls herself one. Unlike therapists, coaches don’t diagnose or treat anything. And unlike supportive friends, they don’t judge, but they do charge to listen. Nonetheless, the practice has become so popular that in addition to about 300 training programs nationwide, universities such as Harvard, Stanford, New York University, and Columbia offer coaching classes or certificates. 

For Ms. Boulanger, the next big do-over event is her biannual, three-day retreat in Southampton on May 11, which she describes as “psychological and emotional detoxing, and spiritual recalibration.” An Ayurvedic-trained chef provides nutritious meals — “to take you on your inner journey” — and there is yoga, an intensive course in the law of attraction, energy healing, stand-up paddleboarding, and even equine therapy. 

“The perfect people always show up,” said Ms. Boulanger. 

Luck of the draw or the law of attraction?