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Gibbs certificate became all the more valuable during the Great Depression, especially among former debutantes now looking for work. Here a 1930s catalog for the school shows two young women on the Barbizon terrace, looking out over the expanse of Manhattan and its possibilities.

If someone had told Katharine Gibbs that one day, through her own efforts, she would find herself living in a grand Park Avenue apartment with three live-in servants, she would not have believed it. But she did just this, single-handedly, by creating the Katharine Gibbs Secretarial School. It was not only a school but also a phenomenon, a pathway for young women to find work, especially at the very moment when most everything else was suddenly closed to them. In New York, Katharine would also create a home for her students: a veritable dormitory, across two floors of the Barbizon Hotel, with curfews, house mothers, and lights-out rules. As restrictive as this seemed to some, it was a liberation for others; a chance for her charges to create new lives for themselves, to forge independent livelihoods despite the odds, much like Katharine herself had done, if not on quite the same scale.

In 1909, already forty-six years old, Katharine Gibbs was suddenly widowed and left with two sons and one unmarried sister to support. It was not a good era in which to be a husbandless, middle-aged, penniless woman (not that there ever has been), but Katharine decided that if her husband had failed to leave her a will, at least he had had the good grace to leave her a fine Protestant name. She felt she could do something with that. Borrowing money from friends at Brown University, she founded the Katharine Gibbs School for Secretarial and Executive Training for Educated Women on Brown’s campus, in a building that is today the Africana Studies Department. A granddaughter of Irish Catholic immigrants who, despite her married name, would not be looked at twice by the Protestant old-money set, she nevertheless marketed to the WASPish upper classes and their not-yet-married daughters graduating from elite colleges. Katharine, as it turned out, was a born saleswoman. Her advertising suggested that her “private” school would protect America’s upper-crust young ladies from the riffraff attending the more commercial secretarial schools, and she did not hesitate to mine the Social Register directories even as she, a single working mother, could never be listed in them.

By 1918, she had expanded to New York. She now advertised in Harper’s Bazaar because that was what the rich read. The school’s 1920 tagline was “a school of unusual character and distinctive purpose,” and Katharine offered seniors at top colleges like Barnard and Radcliffe a shot at limited-enrollment intensive courses for young ladies with “High Academic Standing.” In 1928, the same year the Barbizon officially opened its doors, the catalog for Katie Gibbs—as the school came to be known—pointed out that inherited wealth was “the most uncertain of all forms of protection,” and that the young women who entered Gibbs were looking to make their own living even as they well knew that “a woman’s career is blocked by lack of openings; by prejudice; by the fact that business is outside a woman’s natural sphere; and finally, that she seldom is granted a just reward by way of salary, recognition, or responsibility.”

Despite this feminist ring, a glamorous touch and the whiff of the posh were key to Katharine’s business model. In fact, these provocative words about women’s career opportunities appeared in a catalog that at the same time mimicked a debutante’s dance card—heavy white board, front and back, with a rich white cord as binding. The product fit the very image Katharine was striving for, but it also spoke to the backgrounds of so many of the students themselves, such as Helen Estabrook, who had attended the Bancroft School in Massachusetts, then Vassar College, then the Sorbonne in Paris, all of which she topped off with a Katie Gibbs secretarial certificate—although she knew she would never use it. In 1933, she would marry Robert Waring Stoddard, a founder of the far-right John Birch Society, and use her vast education to become an “impeccably dressed” Massachusetts-based philanthropist, who could hold her own on any topic, from “bird hunting in Scotland to the art of the Bomboccianti in seventeenth-century Rome.”

As the New York branch of Katie Gibbs expanded, it moved its classrooms to 247 Park Avenue, proudly declaring its new location on Manhattan’s only green thoroughfare open exclusively for the use of private cars. The young women studying business administration, speed typing, and shorthand, with no time for a formal lunch, ate their sandwiches at the same tables where they worked, which they covered with green cloths, shaking out the crumbs down onto Park Avenue. It was the Roaring Twenties, and the Katie Gibbs School in New York was filled with young ladies like Helen Estabrook. For them, it was part finishing school and part party school, where they could escape for a year between college and getting married and let their hair down—even if the experience did come with some intense typing practice. But then came “Black Thursday,” and nothing was ever the same again.

The stock market crashed on a Thursday in October 1929. The future British prime minister Winston Churchill was in New York that day and came upon a crowd of people standing on the street looking up at an unfinished skyscraper. When he followed their line of vision, he saw they had mistaken a workman perched four hundred feet up on the girder for a Wall Street speculator preparing to jump. But it was not so outlandish to think they were watching a man about to jump to his death: that day, Americans had lost what the United States had spent on the whole of World War I. By Tuesday it would be twice as much. Syndicated columnist Will Rogers, also in New York on Black Thursday, claimed “you

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