The death of Alfred Pope on August 5, 1913, after a round of golf at Hill-Stead, was an unexpected shock to Theodate and her mother. While Theodate had followed her father's interest in art, he had supported his daughter's desire to remain both unmarried and an independent professional. She had rewarded her parents' confidence in her by creating for them the grandest house in Farmington. However, she felt constricted by their presence and beliefs.

A few years after she had brought her parents to Farmington, she dwelt in her diary on the conflict between conforming to her parents' image of her and living unfettered as she would have liked.

Cannot my body live in this life of luxury and my spirit utterly free itself from the outward life. I will clothe my body to live my life as my parents would have me? Is not my duty to humanity greater than to my parents. How much can I give my parents without taking from what is due to others. In what way can I serve others.¹

There were aspects of her life that she could not share with her parents. She hid from them the depth of her feelings for Mary Hillard and kept secret her relationship with Dr. Dana. The intensity of her suffering burst into expression in several poems confided to her diary. Above all she felt a tremendous need for her parents' affection for her as she was. Even after completing the plans for Westover, her own birthday inspired the following letter to her mother:

Do you really think I am worthwhile. I know on real conventional lines of what daughters should be. I am not a very daughterly daughter. And besides I drink and gamble (at poker) and sometimes lie, yet that is not all I do. Think of me as kindly as thee can seeing me as thee must through the increasing fog and faults that the years surround me with - and have me always - for I am sure thee will do that....²

These feelings of inadequacy were assuaged only after she proved that she could work successfully as an architect - a role which provided an exterior identity which seemed to Theodate far superior to that of a purveyor of charitable acts. Her increasing circle of professional female friends in both England and America bolstered her sense of worth; although she continued periodically to have periods of debilitating depression.

When it came to politics, she was at odds with her capitalist father. She flouted socialist ideas as if throwing down the gauntlet to him. She recollected later:

I was very radical when I was young - as I think every young person should be - and I used to talk about Socialism to everyone who would listen to me. My father was infuriated when he heard me, and my mother told me one day in her room, with her black eyes snapping, "I want to tell you that if you don't stop talking Socialism, your father is going to leave you out of his will." Of course, this impelled me to talking it more and more with delight.

One summer evening when we were sitting on the porch with guests who had dined with us, I began again. I could see my father getting red in the face. Then I said, suddenly, "Why, father, you think that I invented Socialism, and that if I just shut up there would be no Socialist party." Everyone laughed, even my father.³

Her socialist ideas had been fueled in part by her experience at the Henry Street Settlement. There she saw at close range the plight and degradation of the urban poor. Women like Lilian Wald, the Hamilton sisters, and Jane Addams at Hull House were steadfastly trying to combat some of the evils of a capitalist society by caring for the people who fell between the cracks and by educating the children of these people so that they in turn might not be lost. They also felt that if women could vote, then what a difference they might make.

But on the issue of women's suffrage, to which her father was opposed, Theodate remained docilely submissive, at least while her father was alive. This, in spite of the fact that Mary Cassatt and her friend Louisine Havemeyer were avid supporters, and that the painter's correspondence with her Farmington friend is full of references to it. In 1911 the Connecticut state senate passed a bill in favor of women's suffrage to which the conservative Hartford Daily Courant responded by publishing a list of "conservative, home-loving women" who opposed the bill.⁴ Theodate joined her friend Anna Roosevelt Cowles, the leader of the "antis" in Farmington, in adding her name to this list. More pressure of the opposite persuasion was applied in the following year when she joined the Connecticut branch of the Women's Auxiliary to the Progressive Party (Theodore Roosevelt was running for his third term as president on the Progressive plank, which included women's suffrage). This put her in contact with the most vociferous of the local suffragists.⁵ In the fall of 1913, not long after her father's death, she reversed her position, becoming a member of the executive committee in charge of forming an Equal Franchise League in Farmington.⁶ The women's rights issue continued to be a major political concern for the next seven years, during which Theodate continued to play an active role. On March 3, 1915, she spent an afternoon at a hearing on the suffrage bill in Hartford, willing, as she wrote to her mother, "to throw a brick if it would help in showing my seriousness."⁷ And finally, on March 30, 1920, when the issue was reaching its climax and it appeared that Connecticut might not ratify the suffrage amendment, Theodate wrote an open letter to the conservative governor, who was opposed to the bill, in the Courant. Her letter, very tongue-in-cheek, begins:

When you consider the terrible plight of the countries of the world today, are you and the anti-suffragists entirely satisfied that this man-controlled world is the last word in efficiency and wisdom? Have not the men made rather a mess of it?

The starving women and children in Europe and Asia undoubtedly think so as they have suffered most deplorably from it. Do you and the antis fear that, if, the women are given the vote by federal amendment, that they might, by its use, upset the present perfection of our own government? Could women make matters worse than they now are? Why not take a sporting chance that they might improve conditions? ...⁸

And so, devastated as she was by it, her father's death nevertheless had the effect of opening a pressure valve. She approached all matters that deeply concerned her much more aggressively, including her profession. In October of 1913, two months after her father's death, she opened an office in New York and began to work on being invited to join architectural organizations. In 1915 she joined the board of the Society of Preservation of New England Antiquities, which led in 1920 to her being asked with two other architects to plan the restoration of Bulfinch's Old State House at Hartford.⁹ And, although she closed her New York office in December 1915, she became certified as an architect in New York state the following year, after which she joined the American Institute of Architects.¹⁰

On the domestic front she fulfilled her early dream of taking in children, certainly an unorthodox action for an unmarried woman at the time. In 1914, through the State Charities Aid, she acquired a two-year-old, blond, curly-haired boy, named Gordon Brockway, much to her mother's dismay. Having moved into Hill-Stead after her father's death, she installed her new charge with a couple to care for him in the O'Rourkery. Joining Gordon at lunchtime, she made him drawings and watched his learning progress with doting pleasure. It was another, almost unbearable, loss when little Gordon, who had charmed everyone, died of polio two years later on December 21, 1916.