debra boulanger hosts private events at seven on shelter island

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.