When I was in my forties, a civic-minded resident nominated me for a seat on the board of a progressive charitable organization in Boston, a worthy cause with a commitment to economic, educational, and legal advocacy for women and families in urban settings since 1877.
Monthly meetings were scheduled for mid-afternoons in downtown Boston. I took the train in from Salem, leaving my law office for the better part of the day.
I was immediately assigned to a committee, an essential part of board membership. This involved a second monthly meeting in Boston.
The members of the board, connected with the organization for years, were deeply involved in its mission. They were largely residents of Boston and active members of the social scene and its philanthropic endeavors. They utilized their considerable network of contacts to extend invitations to fund-raising events.
I dutifully attempted to learn the ins and outs and fulfill the tasks assigned me. But I felt strangely alienated from the experience. This was an established world of career volunteerism, a significant, in fact indispensable, factor in the social, cultural, and economic fabric of the city. I was a commuter, dropping in but not enough to connect in a meaningful way.
Then, the annual fund-raising campaign began in earnest, the centerpiece of board activity. The chairwoman emphasized the importance of one-hundred percent participation by board members not only to actively solicit donations but to set an example of generosity for other potential contributors. This is normal for charitable boards. But it was not normal for me.
I understood that the way these organizations operate makes the world go round, supporting museums, orchestras, libraries, hospitals, botanical gardens, safety net resources like Rosie’s Place or Big Brother/Big Sister agencies. The impressive army of professional volunteers is highly motivated, focused, and well-oiled.
From that point, I knew I was out of my league. Building a law practice and meeting court deadlines. Striving mightily to balance the demands of career and family life. Trying to save for our children’s college educations and supporting our temple. Spending two days each month commuting into the city in a ritual that provoked increasing anxiety. Avoiding the decision to drop out because I would embarrass the woman who had convinced the board to take on the hotshot North Shore attorney.
I felt reluctant to admit lack of distinction in my new role. I stoically endured instead of facing my mconcerns and cutting my losses. I soldiered on, sensing an imaginary gun to my head.
As an experiment, I drafted a “mock” letter to the board detailing my struggles. Thankfully, I edited it down to omit the apologetic litany. But it was useful to see in black and white what it actually looked like to resign. No one questioned my loyalty or asked me to leave. Writing empowered me to find my voice and clear my path forward.
I composed my final version of the resignation letter and sent it off, with a separate note of appreciation to my sponsor. I felt a huge sense of relief and freedom. I did not fit in no matter how hard I tried.
I regained my confidence and a few years later moved on to become a founder, along with a group of like-minded families, of a non-profit Montessori School north of Boston. This started out as a grass-roots movement, originating with a crisis at another school. We shared a vision that inspired us to give everything we had to make it happen.
Just before the school was set to open, we were slapped with a lawsuit and preliminary court injunction by the former employer of our teaching staff, claiming that the teachers were violating their contracts.
On the day of the hearing, we filled the courtroom, watching our fate played out in a drama more compelling than an episode of LA Law. The outcome was crucial — a continuation of the injunction would effectively close down the school and force the parents to enroll their children elsewhere.
Several days later, we received notification that the judge had ruled in our favor, dissolving the restraining order and allowing our school to open. The next morning, we accompanied our daughter to her delayed first day of first grade, dressed in her plaid outfit and carrying her brand new insulated lunch bag.
Over the years, we expanded from kindergarten to the eighth grade. We raised funds and designed a new building located on the grounds of a nearby college campus. If you were to ask me to name my proudest public accomplishment, it would be the part I played in the creation of a school in the revered Maria Montessori tradition.
And we did this in the late 1980s without cellphones, email, or texting, instead meeting at each other’s homes or talking on the telephone late into the evening, careening from crisis to crisis, from lawsuits to bee’s nests in the rafters.
Inconvenient detours may turn out to be the best possible path after all. I had attended enough meetings of the Boston philanthropic organization over the course of that challenging year to learn the basic workings of a non-profit board and to observe a model of effective board leadership.
I drew heavily on that experience when I was elected to serve as Chairman of the Board of Trustees of the newly founded school, approved by the local Board of Education and building inspector all the way up to the Secretary of State and Department of Education.
But my heart was in it this time, and I was on fire with passion for my cause.
*** School logo designed by CMS parent Deborah Disston