Corporate Retreat at Seven – Debra Boulanger Shares Her Experience

Debra Boulanger shares her experience hosting a corporate retreat at Seven as well as her Shelter Island Top 5.

As a native of Sag Harbor for the last 16 years, Debra Boulanger has a deep-seeded love for Shelter Island and hops the ferry whenever she can. Debra founded The Great Do-Over, a coaching organization that helps professional women navigate a new career as founders of their own businesses.

Last October Debra hosted her annual Six Figure CEO Corporate Retreat at Seven on Shelter Island, where women from her Six Figure Accelerator course stayed at Seven and enjoyed the feeling of the outdoors and tranquility of Shelter Island as they charted their paths to success. Here Debra shares her background, her love of coaching women and what makes Shelter Island so special.

corporate retreat at seven on shelter
Seven on Shelter Island Pool

Tell us about the Great Do-Over

The  Great Do-Over is a coaching and mentoring business for women leaving the corporate world and starting their own businesses as coaches, consultants, speakers or other entrepreneurs.

What led you to starting The Great Do-Over?

I had spent over 25 years in the corporate world and at one point, I was burned out. At the same time, on a personal level, I was heading for divorce, my mother’s health was failing, I had a 13-year-old son. Everything felt like it was coming into collision, and I had to reinvest myself and decided to start a coaching business after my own personal reinvention, which I called my Great Do-Over. So I named the company after that. 

What sort of services do you offer?

I support women leaders who are making the leap from corporate to entrepreneur. It’s generally three service offerings. There’s the launch lab, which is the first stop on the path. It helps answer questions about what you’re offering, like how do you package it? How do you price it? How do you get clients? That’s why we created the launch lab for women entrepreneurs. It’s a four month mentorship and mastermind program to get started and create those first revenue generating activities.

After that, my clients ask me, well how do I grow my business? How do I get new clients, speaking engagements and get on corporate stages? How do I develop an offering portfolio to handle more than one customer segment or to have a longer engagement with clients that I have? How do I increase the customer lifetime value? This is a six figure accelerator that’s one year long with women entrepreneurs who are eyeing six figure revenue growth in their business. But, whether they’re making $50,000 or earning more than six figures in their practice, this is for women who want to accelerate it, double revenue or grow revenue by a predictable six figure growth margin year over year.

The third program l launched is how to stand out in webinars. It’s helping my clients who have to create online seminars that are informative and engaging. It’s how to get new clients everytime you speak. 

Many of my clients take all three courses and end up building a good deal of momentum and attend our six-figure growth predictor corporate retreat, which I held at Seven. That was the retreat, which is part of the experience in getting women from our weekly group calls together. Once or twice a year we get together as a community to nurture ourselves as CEOs of growing businesses. It’s to stay connected to their mission, vision and values. It’s increasing our own skills and the capacity to lead an ever growing business.

What fields do most of these women come from?

Oftentimes it’s coaching and consulting in leadership coaching, like C-suite executives, or career coaching. I also do sales coaching, non-profit fundraising. There’s a broad spectrum of skills. Sometimes I’m helping people improve their speaking skills. Other times it’s a focus on specific industries, like holistic or wellness, to grow their revenues and impact. So each client’s work is based on their own mission. 

What is it about age and wisdom that can lead people to finding their next passion? Do you feel like it can only come with age?

What’s been really interesting for me is that my clients are getting younger and younger. A good portion of women I work with are in their thirties. I work with everyone from women who’ve excelled up the corporate ladder and are now rethinking their next phase, to a former Olympic figure skater who’s transitioning into an executive coach and leadership coach. I’m helping give them the skills they need in strategy, pricing, packaging, messaging and sales skills. 

What are some of the trends you see among the people you work with? What are the pin points or fear factors involved in starting over and how do you try to alleviate those?

There’s a lot of fear when they first start out. Most of my clients are successful business leaders and c-suite executives who have established success in their career, and then they’re making the leap to decide to launch a business starting from scratch. Although they have incredible skill-sets and talents developed in the corporate world, when you launch your own business, you’re also cmo, cfo, ceo. So suddenly, it’s how do I get good at sales? How do I market my services? How do I get in front of new clients? How do I speak from stages? All the other skills are a stretch, plus there’s no corporate paycheck. There’s no team supporting you to get all of your work done. You have to build a team from scratch. Hire and delegate as much as you can afford to so that it will free up time on business strategy.

Tell me about your Six Figure CEO Corporate Retreat at Seven last October….

The world was just opening up after the pandemic. I was looking for a space that would be luxurious as well as constrained and safe for clients that would also exude luxury. These are my most valuable clients. I wanted to give them a high end experience and that was everything like the environment in the decor of the house. Style is really important to me and the fact that Beth had spent so much time and effort in the design of the rooms and the overall luxury experience of her inn was really luxurious. Her attention to detail, from the sound bowls in the enclosure by the pool, to the breakfast laid out in the morning, to the art on the walls, the furniture choices. Each room was outfitted so perfectly for the experience I wanted to create for our clients. 

seven on shelter is a beautiful island bed and breakfast in new york great for corporate retreats

Why is Shelter Island so special?

The experience of stepping away from the day-to-day to go on a ferry is very symbolic. You’re leaving the mainland behind, over water, and arriving somewhere else. There’s a big exhale. It’s so beautiful and welcoming there and we were blessed with a gorgeous weekend in late October. It was 70 degrees. It was incredibly beautiful. We spent time outdoors, walking Crescent beach daily. It was a great environment for our clients to have time away in nature and to join us for meals and the programmed events we had. 

Debra’s Shelter Island Top 5: 

Salt: “This seaside is one of my favorite summertime haunts. I love the fresh seafood and being right on the harbor.” 

Mashomack Preserve: “There’s nothing quite like a walk through Mashomack anytime of year, but particularly in the autumn when all of the leaves turn. It’s the most peaceful thing. I’ve lived in Sag Harbor for 16 years, and hiking Mashomack is always such a treat.” Read more about Shelter Island hiking in our article here.

Crescent Beach: “This the beach where we walked every morning on the Six Figure CEO Retreat when staying at Seven. It’s so beautiful, especially when it’s so calm before the boats start to come in.”

Marie Eiffel Market: “A must-stop if you’re in town, Marie Eiffel has the freshest produce, most delicious baked breads and yummy grab-and-go items to take on your beach picnic. It’s no wonder it’s one of the busiest stops on the island.”

Vine Street Cafe: The most perfect and delicious setting for dinner on the island. The food is “special occasion” worthy and yet it’s so charming and relaxed – just like the rest of the island. Read more about Shelter Island Restaurants to try in our article here.

*The Debra Boulanger portrait in this article is by Alyssa Peek.

Amelia Clark on the Shelter Island Ferry and More

Amelia Clark Practically Grew Up On The Shelter Island Ferry

If there’s one person you could consider the eyes and ears of Shelter Island, it might be Amelia Clark. The college junior was raised on Shelter Island and is part of the legendary Clark family that’s run the South Ferry since the 1800’s. She and the rest of her Clark crew work hard year in and year out making sure everyone coming from the Hamptons gets on and off the island as efficiently and safely as possible. To say she and her family are the heartbeat of Shelter Island would be an understatement.

Amelia Clark | Photograph provided by Amelia Clark

When she’s not issuing tickets on the ferry, you’ll find Amelia working at Shelter Island’s most high-end restaurant 18 Bay, babysitting some local kids, and even popping her head in at Seven! So naturally, we had to find out Amelia’s top Shelter Island picks and what she loves most about this magical place. 

Tell us about your family and the Shelter Island ferry…..

I believe we are the oldest family run ferry company on the East Coast, but it’s always been our family that ran it on Shelter Island. The house I grew up in was the original ferry house, and right outside our house is where the ferries dock at night, right on the beach. 

My grandfather and his brother run the ferry together. Before that it was their dad. My dad is the scheduler for the ferry. He’s worked there ever since we’ve lived there. My mom worked on the ferry when she was pregnant with me. I started training to work there over winter break.

How did that go?

It was really fun. There’s a lot of technicality to it. When you’re charging people, you have to go by different prices, sizes, lengths, and how many people are in the car. You have to take all of that into account. So there are a few different formulas. I’ll probably have to get retrained for summer because going back to school fills my brain back up, but it’s really fun. People who work there are so nice. We’re big on having a positive attitude and always being kind to everyone. Who would want to work somewhere that’s not a positive environment? No one wants that reflected onto them.

Is there ever any friendly competition with the North Ferry service?

18 Bay | Shelter Island Restaurant | Photography by Doug Young*

I don’t think about it as competition. They take people to the North Fork and we take people to the South Fork. Typically people will go through both of us depending on where they’re going, so I don’t think of it in a competitive way. I believe the North Ferry is a corporation. They do things differently. They are advancing more technologically, for example they have scanners. We haven’t gotten there yet, but I’m not sure we feel like we need to. 

Tell us about the training process….

It’s really hands-on. When you’re training, they have a trainer with you. So first you’re walking around with him or her for a bit to see what they do. Slowly, they implement different tasks, at first you’re loading and unloading and opening the gates. Then once you have that down, it’s OK, now you’re going to go to the windows, get money and click tickets. OK that sounds like a plan. I got that down. Then you keep doing it over the course of a week, and your trainer is there to let them know if you need any help with anything. I won’t know everything right away because there’s so much to remember and recheck up on. But everyone’s so nice and so helpful about it. A lot of people come across with a commuter or resident pass, so if you know the price of a car typically then you’re fine. 

What’s life on Shelter Island like now compared to when you were growing up?

Shelter Island Ferry | Photograph by Doug Young

I feel like it’s changed a little bit. The North Fork is getting “hamptonized,” so to speak. I can almost see it in some cases and feel it coming to us, just the people and the changing of businesses and the new businesses that come around in the summer. It’s like when I used to go to Sag Harbour as a child, it was very similar to Shelter Island. They were two small towns, but the vibe has gotten different as I’ve gotten older and it feels like it’s spreading through to here, too. I think we have a doctrine that we can’t have chains or fast food, but I can feel it spreading in different ways.  

What was it like to grow up on Shelter Island?

Shelter Island Ferry Captain | Photograph by Doug Young

I loved it. It can be complicated in some ways. There were small classes, I mean 23 kids were in my graduating class senior year. But it’s like a little family inside a bigger family. The population all year ‘round is not very big and you’re surrounded by the same kids your whole life. So their parents are your pseudo parents and they check up on you and support you. You always see your teachers around. You see them in the summer on the beach. But you can have amazing experiences because the classes are so small. You get to go on a Schooner trip in seventh grade. We went to Disney World in eighth grade. We get to go see Broadway shows fairly regularly. We also just feel like we have a lot of support that makes itself available to us.

Do you think you’ll stay on Shelter Island?

As nice as I think it would be to raise kids on Shelter Island, at some point I’d like to go away for a bit. I plan to summer here myself, and I’ll probably move back when I’m older, but I’ve always enjoyed big cities and really crowded places. I actually like background noise when I sleep. Shelter Island is eerily quiet at night for most of the year, so that’s made it difficult for me to sleep. My parents crack up. They used to take me to music festivals in New Orleans and Austin, and the noise would always help me go to bed. That was not the case for them. I’ve always felt comfortable with more people. I’m going to try to embrace that more.

What do you love most about Shelter Island?

The sense of community. It’s always been the best thing. I’ve always felt taken care of. Everyone looks out for you. I was so involved at school so I was my cousins’ TA in their art classes. When my cousin was in kindergarten, I was a TA in that class, too. And just even the involvement of babysitting. I babysat so many of those kids I’m a junior in college, so these kids I babysat are getting into middle school and high school, and I’ve watched them, all of them. All their parents know me.

Amelia Clark with family and friends at Shelter Island’s South Ferry | Photograph provided by Amelia Clark

Amelia’s Shelter Island picks:

Maria’s: “I love Maria’s. That’s always been my favorite place to go if we wanted to get food after school. The food is great, and in the summer it’s awesome to sit outside. Maria is a sweetheart. I went to high school with both of her kids. She always talks about her kids when I come in, and asks me how I’m doing. She always checks up on me.

The beaches: “Shelter island has the best beaches. Crescent Beach is awesome. The sand is less rocky. If you get there earlier, it’s really great. And everywhere is so safe. Our joke is that we don’t have a key to our house. We don’t lock our car doors. The beaches are also so safe.

18 Bay:  “Jimmy is the manager and Chef Adam and Elizabeth are the sweetest people. I’ve worked there since I was 16. They’re my other family. They check up on me all the time and are so supportive. The food is so good, too, and the menu changes every week. Sometimes they let me eat there.

Greenport: “There are so many cute shops and places to eat. I really like this one little shop called Tea and Tchotchkes. They sell crystals and really cute clothes and self-help books and tarot cards. I love going in there. I’ll go once a week to stand around and get crystals and a necklace or something.

Grindstone Coffee and Donuts, Sag Harbor: This place is so good. On Shelter Island we don’t have a lot of fast food. There’s no Dunkin Donuts etc. I’m not even a big donut person, but I love going in. It’s also across the street from Whites Apothecary, which has so many nice skincare and makeup brands. I love going in and debating whether I can afford to buy anything.

Stars Cafe: I love that place so much. They’ve got the best muffins and bread every morning, especially in the summer. They also make the best breakfast wraps and sandwiches. Right door is the pharmacy, which is really the pinnacle place on Shelter Island. The milkshakes are top tier.

Read more about the top things to do in Shelter Island here.

*View more photographs by Doug Young here.