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Not-for-Profit, Award-Winning Community News and Views for Windham County, Vermont • Since 2006
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Jeff Woodward

Michelle Simpson has stepped down as head of the Downtown Business Alliance.


Brattleboro business community leader moves on to new challenge

Simpson leaves DBA and Oak Meadow to lead fashion-design school in Boston

BRATTLEBORO—After nine years at Oak Meadow and three on the board of directors for the Downtown Brattleboro Alliance, Michelle Simpson is leaving the local workforce for points south.

In August, Simpson joins her fellow Vermonters who divide their time between the Green Mountains and an urban center. Simpson takes the helm as executive director of the School of Fashion Design on Newbury Street in Boston.

Simpson said she looks forward to “stewarding a special place in the heart of a retail environment.” While the School’s building is surrounded by stores and franchises, the School itself is independent.

“It’s an innovative maker-space where people are being creative,” she said.

Simpson expects a huge learning curve.

“I myself don’t sew,” she laughed. “I’ll have to learn the language of the faculty and understand that [fashion] landscape better.”

The School of Fashion Design, which opened in 1934, offers a three-year certification program. This interests Simpson, who supports competency-based education and alternatives to the conventional four-year college degree.

“Fashion has driven human history,” she said. “Design, art, function, adornment. These things are very human.”

“But the industry has also degraded the planet,” Simpson continued. “SFD can be an innovative design hub where the graduates are problem solvers and ‘solutionaries.’”

It feels like a good time to move on, Simpson said of the Downtown Brattleboro Alliance during a recent interview. She feels good about her accomplishments as president of the board.

The DBA participates in Vermont’s downtown improvement program. As part of the program, the municipality applies to receive what is called a downtown designation. The municipality then identifies an organization to focus on meeting the state’s program requirements and supporting the downtown’s vitality.

Under Simpson’s leadership, the town’s designated downtown organization helped raise the visibility of Brattleboro in the communities within driving distance of town, she said. The organization, she said, helped “reinvigorate the downtown merchant community.”

Simpson chose highlights from “a pretty long list” of projects and events held by the organization that she is proud of. The flower and holiday lights program, for instance.

She also noted projects where the DBA collaborated with other organizations. She listed the annual Luv Crawl, the Golden Ticket giveaway where people can win free parking for a year, Elliot Street Block Parties, and the county’s new events calendar, Planagogo.

The DBA itself underwent organizational improvements such as updating its bylaws and reestablishing the executive director position, Simpson said.

Missing pieces

Simpson said some of the things she’ll miss about working in Brattleboro are, ironically, the same qualities that impede the town’s development: the community’s thoughtfulness and caution, and the slow process involved in achieving some kind of consensus.

“That’s what makes Vermont so great,” Simpson said.

She also noted the importance of supporting community spaces. “Investment in our downtowns and Main Streets is critical,” Simpson said.

“Downtowns are fragile and valuable,” she continued. “And organizations like the DBA need to be funded so that they can take the lead in assisting the community in innovating and developing Main Street for everybody.”

Retail has changed so much, Simpson said, asserting that traditional retail is basically “dead.” It’s important to train and support business owners on how to shift their organization so that it can create experiences that online shopping cannot, said Simpson, who envisions a downtown that serves as a “community gathering place where retail supports the experience.”

“But you can’t support free [events or experiences] without getting revenue from somewhere else,” she added.

Simpson encourages everyone to serve the community by volunteering on a local board, rather than sitting back and being critical.

“The online Facebook environment can really be demoralizing to people who are volunteering their time to community work,” Simpson said. “Instead of being critical, join a committee.”

Simpson’s term as board president ends in September. She anticipates the board will nominate an interim president who will serve until September. Then, the board will elect a new president.

“I’m always available in a consultant capacity,” Simpson said, laughing.

A difference in opinion

Leaving Oak Meadow, Simpson said, feels “bittersweet.”

Oak Meadow provides home-school curriculum for grades kindergarten through 12.

Simpson “transitioned out” of her executive director position in January. She worked for the organization for nine years, with seven of those as executive director.

One of the reasons Simpson felt it was time to leave Oak Meadow was because of its for-profit status, she said. According to Simpson, she attempted unsuccessfully to purchase the organization and transition it into a nonprofit school.

By their definition, Simpson said, for-profit organizations serve their investors or stockholders. Nonprofits, in her view, serve their community, or in a school’s case, its students.

“Nonprofits can be profitable,” Simpson said.

She will miss the global community of staff, faculty, students, and families involved with Oak Meadow.

According to Simpson, she and her colleagues accomplished “so much together.” These accomplishments included a reorganization, a rebranding, an increase in staff, and becoming the first accredited distance learning school. Oak Meadow is accredited by the New England Association of Schools and Colleges.

Oak Meadow occupies space in two buildings: The Brooks House and Cotton Mill. It employs approximately 60 people in Brattleboro.

Simpson said Oak Meadow helped her recognize her own skills.

“It helped me recognize my talent as a strategist and my ability to bring a team together to execute a strategy,” she said — a skillset that Simpson plans to take with her to the fashion institute is her belief in ethical leadership.

It’s a leader’s job to identify people’s unique capacity and talent, she said. A good leader then strives to bring out those talents to best serve the group and its mission.

“That’s what leadership means to me, is honoring who people are,” she said. “People have to be inspired about the work they’re doing.”

As Simpson prepares to take on her new role in Boston, she considers what it means to be a woman in leadership.

In Simpson’s experience, she has operated in mostly male-dominated arenas. As a self-described “heart-centered collaborator,” she said she automatically challenges the paradigm. She said this has led her to sometimes question herself or feel self-doubt.

“Leaders must always be in touch with their deep consciousness and heart,” she said. Otherwise, Simpson said, they will operate from a place of “ego and power.”

“Women have to have a lot of roles as it is — mother, daughter, sister, friend — add to that professional or leader or CEO, and it is a really tall order.”

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Originally published in The Commons issue #465 (Wednesday, June 27, 2018). This story appeared on page A4.

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