A year later, in 1885, Sarah Porter hired her to teach at her long-established girls’ school in the village of Farmington, a few miles west of Hartford. It was to Mary Hillard’s advantage that when Miss Porter hired a teacher, she was less interested in her education than in her character—“a clear and well-trained mind, quick sympathies and a pure heart” were what she wanted. Perhaps the headmistress at the age of seventy-two saw the twenty-three-year-old Mary as a younger version of herself; both were descendents of old American families and daughters of Congregationalist ministers. There were some differences, however: Sarah Porter, whose brother was the president of Yale University when she hired the young teacher, was a scholar who had studied languages and other subjects with Yale professors throughout her life. A pious woman who dressed in handsome black dresses in winter and gray ones in summer, she was also a person who valued simplicity and humility and was supposedly indifferent to the social backgrounds of her wealthy pupils, preaching that “wealth did not make worth.”
Young Mary Hillard was deeply impressed by this woman, who became a mentor. She admired the way the older woman impressed old-fashioned values upon her pupils to prepare them for family life rather than for teaching, missionary, and other kinds of women’s work. Yet unlike traditionalists who believed that the female body did not have enough blood to sustain both the brain and the womb, Miss Porter also rejected the idea that mental activity undermines a woman’s family responsibilities, and she attempted to prepare girls for lifelong intellectual and spiritual growth. Mary Hillard later said that she was very grateful to Sarah Porter for teaching her everything she knew about successfully running a school during the six years under her wing.
Those years of her early twenties were the time when the lovely Mary Hillard would have been most likely to marry. An old friend of hers acknowledged that Mary had been in love as a young girl, and that she had struggled “to decide between love and duty.” Teaching evidently tapped her idealism: the little girl who had wanted to be a missionary in China now wanted to enlighten and lead young women. If she married, she knew that she would eventually have to give up teaching; wives almost always left or lost their jobs especially after the arrival of children. At that time she expressed caution about romantic feelings. Miss Hillard has “some queer ideas, such as that a girl should never love a man before he asks her to and then she cannot be certain whether she can care for him or not but must wait to find out,” confided Elizabeth Failing, a Miss Porter’s pupil, to her diary. Miss Porter viewed romantic infatuation as a feeling to be directed toward the good of the family, a view the young teacher would also articulate. At the Westover graduation of 1917, she declared that marriage is not for personal happiness but a way to pass along values to the next generation.
Even at that early age, Mary Hillard had a knack for understanding girls; Elizabeth Failing also wrote in her diary that she was in awe of her teacher’s insight into her at a party where Miss Hillard told fortunes and placed an apt quote about each girl at her plate. The girl also wrote about her admiration for her energetic and entertaining young teacher: Miss Hillard is, she wrote, “like a breeze [that] stirs up the air and implants a new vitality.” Still, Mary Hillard came to regard herself as less gifted as a teacher in the classroom than as a leader who could inspire young women with her melodic speaking voice. Miss Porter noticed her leadership qualities and soon gave the youthful teacher a small administrative role in one of the school’s dormitories.
Mary Robbins Hillard as a young woman. L. ALTMAN & CO.
By that time Miss Porter had already chosen her successor, assistant principal Mary Dunning Dow, a former pupil and a widow who was much older than Mary. At the same time, the scholarly and elderly headmaster of St. Margaret’s School in Waterbury was looking for an assistant. His wife had recently died, and one day during a visit with a parishioner he confessed his difficulty in trying to run the girls’ school alone. The woman, whose daughter had roomed with Mary Hillard at St. Margaret’s, mentioned the young teacher as someone with energy and ideas; one thing led to another, and Dr. Russell offered Mary Hillard—whom he had asked to leave the school some fifteen years earlier—the position of assistant principal. When she told Miss Porter about the offer, the older woman urged her to take it, telling her that she had a talent for leadership. Mary’s reservations were about leaving the peaceful village of Farmington for the busy city of Waterbury. Also, she had enlarged her circle of friends in Farmington to include more sophisticated people than those in the parsonages of her youth. Miss Porter assured her that she would find similar people in Waterbury, like the fine old New England family of Edith and Frederick Kingsbury, who had two daughters her age living at home. As Mary Hillard turned twenty-nine, she decided to go.
As Miss Mary Hillard walked rapidly through the streets of Waterbury in the autumn of 1891, she carried herself with more dignity and solemnity than usual, aware that she was being observed. A tall, slender, single woman with searching eyes, she was remembered for parting her long, dark brown hair in the middle and pulling it back into a knot at the back of her head. Instead of elaborate Victorian fashions, she wore the more practical clothing of the professional women of her day. “There was an air of austerity mingled with something athletic,” an observer recalled. “The shirtwaist with a collar and bow tie, the longish skirt, the absence of anything colorful, the modest hat, gloves, all bespoke restraint.” She brought a pearl-handled knife to St. John’s Episcopal Church in the city, where St. Margaret’s trustees and most of its pupils worshipped, to cut tight corset strings of girls who fainted during services. Although young men were awed by her, she got to know several Yale graduates who worked for The Waterbury American as well as families who knew her father. Direct and businesslike, she gave people the impression that she knew what she wanted and had no time to waste. “There were inner fires always burning in her,” observed a younger friend, the Rev. John T. Dallas, assistant pastor at St. John’s, who would get to know her very well.
Her sense of urgency was undoubtedly exacerbated by the realization that St. Margaret’s was in debt and in decline. She had quickly discovered problems with the school’s faltering furnaces and its drafty, dilapidated Victorian wooden structure. About a year after her arrival, Dr. Russell became ill, entered a New York City hospital, and sent in his resignation. The board of trustees asked Mary to take his job. In an act of astonishing audacity by a woman barely over the age of thirty, she said no. Instead, she responded with a counteroffer in which she proposed to rent the rambling building from the trustees and run St. Margaret’s as her own school. As gestures to reassure the trustees, she offered to hire Dr. Russell, who had remained in New York to teach theology, as rector and to meet with them once a year.
Mary Hillard obviously did not want to be under the thumb of older, more cautious male trustees who, she feared, might not be willing to borrow enough money to turn the school around. She felt supremely confident that any debts she took on would be eventually repaid as she increased enrollment. The trustees, including Frederick Kingsbury, must have been taken aback by the demands of the young woman, but by 1894 they agreed to them. Kingsbury, whose mother had gone to Miss Pierce’s School in Litchfield, was a firm believer in women’s education and most likely in women educators as well. The young headmistress was equally persuasive with Waterbury bankers. At the end of every school year, when tuition income ended and teachers had to be paid and repairs undertaken, she would take out a personal bank loan endorsed by Dr. Russell simply on the strength of a handshake.
It was during this time in the late 1890s when she began to hire the teachers a few years younger than herself who would follow her to Westover and be lifelong friends. She asked Helen Dean LaMonte, a member of the Smith College class of 1885, to teach art history and literature. Lucy Bailey Pratt, a teachers’ college graduate, took charge of the kindergarten. She also hired Henriette Coffin, a young Frenchwoman, to teach the French language and literature, and Helen Andrews, an artist, to teach drawing and painting. In 1900 her younger sister, Fanny, was teaching psychology and history at the school, but she, like their oldest sister Martha, gave up teaching when she married. During the first decade of her sixteen years at St. Margaret’s, Mary borrowed and repaid huge amounts of money for repairs and, with the help of a gift in 1902, finally got the school