Dickinson, Anna E. (1842–1932)

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Dickinson, Anna E. (1842–1932)

Popular American abolitionist who championed the idea of civil rights for women and blacks, achieved fame for her passionate political speeches, and helped redefine the role of women with her success. Born Anna Elizabeth Dickinson on October 28, 1842, in Philadelphia, Pennsylvania; died from cerebral apoplexy on October 22, 1932, in Goshen, New York; daughter of John Dickinson (a merchant) and Mary (Edmonson) Dickinson; received formal instruction from the Friends Select School of Philadelphia and the Westtown Boarding School until age 15; never married; no children.

Showed dedication to abolitionism and women's rights at an early age; published an anti-slavery essay at 13 (1855); started working at 15 (1857); at 17, delivered her first public speech on women's rights and within two years became the most popular female lecturer on abolition and equality of women in America (1859–61); lectured throughout the Northeast for the Republican Party (1863), which led to a profitable career in political campaigning; continued lecturing throughout the country about civil rights for women and blacks; began career as novelist in mid-20s; wrote her first novel (1868), second (1876), and third (1879); wrote plethora of plays and debuted as an actress (1876); resumed political campaigning for the Republicans (1888).

Novels:

What Answer? (1868); A Paying Investment (1876); A Ragged Register (of People Places and Opinions) (1879). Plays: A Crown of Thorns, or, Anne Boleyn (1876); Laura, or True to Herself (1876); Aurelian (1878); An American Girl (1880).

An attractive teenager shocked an audience and sparked a heated debate at a gathering of the Pennsylvania Anti-Slavery Society when she baldly stated: "The Constitution of the United States recognizes human slavery, and makes the souls of men articles of purchase and sale." Meeting near Philadelphia in 1860, the abolitionist society had come together to discuss the precarious state of the nation and the Dred Scott decision that declared slaves as property. Although some abolitionists could not concede that America's great founding fathers condoned slavery, 18-year-old Anna Dickinson went on to assert that "if the word slave is not in the Constitution the idea is." Declaring that "certain fundamental ideas of

right" were universal and the "laws of man's making which trample on these ideas are null and void," she questioned the sincerity of American democracy and demanded specific laws be designed that would curtail racial and gender discrimination. Her ideas provoked some angry reactions, but Dickinson's articulate speech and utilization of examples to defend her beliefs gained the attention and respect of many prominent reformers. This event, her first speaking engagement before a sizeable audience, revealed a talent for persuasive speech. A reporter from the Philadelphia Press noted that "Miss Anna E. Dickinson, … eloquent beyond her years, made the speech of the occasion."

As an adult, Dickinson would achieve unprecedented popularity as an orator and champion of civil rights for women and blacks in America. Throughout history, politics and public speaking were identified as masculine activities and deemed unsuitable for women. Her political involvement and unprecedented success as an orator expanded society's notion of women's intellectual capabilities and helped to remove the cultural barriers that prevented women from speaking in public.

Born in Philadelphia, Pennsylvania, on October 28, 1842, Anna Dickinson was the second daughter and fifth and last child of John andMary Edmonson Dickinson . Anna's devotion to abolitionism and women's rights stemmed from the ideology and activism of her family. Typical Quakers, the Dickinsons vehemently opposed slavery; often their home was utilized as a stop on the underground railroad. Anna's father, a dry goods merchant of meager means, possessed a talent for oration and devoted himself to abolitionism. Shortly after inspiring his community with a passionate anti-slavery speech, he suffered a heart attack and died. Anna, only two at the time, vaguely remembered him, but she was inspired by her mother's recounts of his dedicated activism.

Mary Dickinson also instilled the idea of gender equality in her daughter by reciting tales of Anna's ancestors. Within the Society of Friends, which encouraged female activism, her great grandmothers had served as preachers and were renowned for their eloquent and stirring sermons. Anna's parents had both descended from prominent families who had settled in America during the 17th century; despite their genteel lineage, the family was often impoverished. John Dickinson's untimely death left his family destitute and deeply in debt.

Henry Ward Beecher">
Among the women of America who have broken down the prejudice of public speaking by women none has been more eminent than Anna E. Dickinson.
—Henry Ward Beecher

Struggling to sustain the family, Mary Dickinson accepted boarders and occasionally taught privately. Because she imbued her children with the Quaker tradition, Anna received a more complete education than many women of the time. She immersed herself in classical literature, poetry, history, ethics, Shakespeare, and the Bible; reading became her favorite pastime. In addition to the classical collection chosen by her mother, Anna secretly devoured the popular verses of Lord Byron, of whom Mary disapproved. At approximately age ten, Anna attended the Friends' Select School of Philadelphia, and for a brief interval received instruction from the Westtown Boarding School. Increasingly interested in abolitionism, Anna gleaned information about the national debate over slavery from the local newspapers. When she read of a Kentucky schoolmaster who had been tarred and feathered for writing an anti-slavery letter to an Ohio newspaper, she was incensed and wrote an essay that was published by the Liberator, William Lloyd Garrison's abolitionist newspaper, in 1856. "Can any man in this country … stand up firmly and say 'I am free,' when such evils and wrongs are constantly being enacted among us, without one word or act of denunciation?" wrote the 13-year-old.

The Dickinsons' financial problems continued, however, and at 15 Anna left school and sought employment to help support her family. (Her brothers Samuel and Edwin were both sickly and had unsuccessful careers; John taught religion and math at a college, while Susan Dickinson , a lover of the arts, taught for a short while before assuming the running of the household.) Briefly, Anna served as a copyist for a local law firm and publishing company; unsatisfied with this position, she embarked upon a career of teaching. "Mother wants thee, if thee can," wrote her sister Susan, nine years her senior, "to come home next seventh day prepared to pay the ice bill." During this time, Dickinson's participation in anti-slavery activities increased, and she also became an outspoken advocate for women's rights.

Raised to believe in gender equality, Dickinson was shocked by the blatant prejudice she experienced in the work force. Temporarily serving as assistant teacher in Beaver County, she applied for a full teaching position in a nearby school. Since society devalued the work of females, working women were often paid much less than men holding the same position. Inquiring about the teaching job, Dickinson was informed that a woman's salary would be $16 per month, whereas the male teacher who had held the same position earned nearly twice that amount. Outraged at the discrepancy, she wrote the school's administrator: "Are you a fool or do you take me for one? Though I am too poor today to buy a pair of cotton gloves, I would rather go in rags than degrade my womanhood by accepting anything at your hands."

Dickinson soon discovered that gender discrimination was not limited to the work force. In 1860, she attended a debate entitled, "The Rights and Wrongs of Women," sponsored by a local organization. Only 17, Anna unexpectedly became involved in her first debate when, appalled and angered by comments of a male speaker who was using his daughters and their abilities as yardsticks for womankind, she retorted:

You say that what your daughters cannot be, no man's daughters can be; that your daughters are incapable of being doctors, lawyers, priests, businessmen, bank presidents, authors, editors. In one word, as you yourself have summed it up, your daughters are fools! And, in heaven's name, what else is to be expected of the daughters of such a father?

This quick repartee marked the first step in her career as an orator. As 19th-century ideology relegated women into domesticity and essentially banned them from the public sphere, Dickinson's outspoken actions attracted attention. The idea of a gifted young woman aroused much curiosity; a novelty, she was invited to other local meetings. After her ringing declaration at the 1860 assembly of the Pennsylvania Anti-Slavery Society, she quickly developed a reputation as a skilled orator and devoted abolitionist. Her impromptu yet cogent speech impressed many, and soon she was befriended by Lucretia Mott and Dr. Hannah Longshore , distinguished reformers and active supporters of women's rights. Encouraged by her mentors, Dickinson addressed an audience of nearly 800 in the Philadelphia Concert Hall in February 1861. Her lecture, pointedly titled, "The Rights and Wrongs of Women," captivated the audience for nearly two hours and secured Anna immediate recognition in reform circles.

In spite of Dickinson's first oratorical achievement, pecuniary problems once again befell her family. The military enlistment of many men during the Civil War had created thousands of vacant jobs, and Anna easily secured employment at the U.S. Mint in Philadelphia. There, she earned $28 per month, much more than she had procured as a teacher, and, having Sundays off, she was able to attend abolitionist meetings. While addressing the Pennsylvania Anti-Slavery Society in the fall of 1861, Dickinson accused General George B. McClellan, the commander of the Army of the Potomac, of treason. McClellan's extreme military caution and well-known sympathy for slave-owners had created some speculation, but Anna's brash accusations remained unfounded. News of her speech spread, and within the week she was terminated from the mint.

After the abrupt dismissal, Dickinson visited a friend in Rhode Island and promoted abolitionism throughout New England. After hearing Anna speak on "The National Crisis" in Newport, the correspondent of the Providence Press proclaimed: "To witness the boldness of her manner, speech, and gesticulation, one is almost led to the conclusion that she needs only the sword, the charger, and the opportunity to become a second Joan of Arc, and … lead the 'grand army' on to victory and war."

Despite Dickinson's increasing popularity as a lecturer, her mother and sister remained

impoverished. Both Edwin and John would not send money, believing their sisters could care for themselves. Needing to secure substantial paid employment, Dickinson sought assistance from William Lloyd Garrison in the spring of 1862. Her eloquence had so impressed him that he arranged a series of engagements for her but warned her to speak up: "Most of the female lecturers fail for lack of voice and this has led those who are opposed to female speaking sneeringly to say, that if God had intended it, he would have given the necessary vocal powers." In April, among eminent speakers Ralph Waldo Emerson and Wendell Phillips, Dickinson addressed nearly 5,000 at Boston's Music Hall. Only 19, she argued the causes of abolitionism and women's rights before some of the most venerable reformers of the time. Once again, her powerful and emotional oratory affected many: Susan B. Anthony , the most revered advocate of women's rights, encouraged her to speak about women, and a lasting friendship was formed.

There was a side of the supremely confident Dickinson, however, that the public never saw. She had been terrified before the speech, in deep and inconsolable depression, sleeping little the night before, unable to eat the day of. Garrison wrote an abolitionist friend of hers, Elizabeth Buffum Chace : "It must be a great trial and even danger, to so young a person, to be the object of so much interest, to receive so much public applause, and to possess so great and happy a talent for holding and swaying the minds of large audiences." These pre-speech depressions and crises of self-confidence would eventually take a toll. But Dickinson was ecstatic over her reception, writing home: "One would suppose that 'no sich' had ever been seen in these quarters. Mr. Garrison says he has been over-run with thanks for finding me. However, I will stop blowing my own trumpet, being somewhat out of breath." To which Susan replied after suitable approbation, "Mother wants to know whether, if she gets the parlor chairs done up, a matting for our floor, and one or two little matters done up in the furniture line, thee can spare her money enough when thee comes home to pay the bill," while mother Mary advised, "Beware my child of being carried away by the voice of adulation."

Thrilled by her accomplishments, Dickinson suffered disappointment at the transience of success. Once again unemployed and broke, she returned to the family's home in Philadelphia. Scheduled to speak in Boston in the fall of 1862, she spent the summer preparing for a new speech, "Hospital Life," by interviewing wounded soldiers in army hospitals. Although she was an inexperienced female, only 20 years old, she received $100 per speech, the same amount paid to prominent male orators Henry Ward Beecher, Phillips, and Emerson. Despite Dickinson's increasing prestige and success as an orator, work was generally seasonal; immediately after a significant speech, she was often unemployed. By winter of 1862, her family, still dependent upon her for support, faced insolvency; in December, she lectured to soldiers for only $15–$20, but, by doing so, she managed to sustain herself and her family for the month.

At this time, there was unrest with the electorate throughout the United States. Many saw the war as a crusade to restore the Union, not as a conflict over slavery. Lincoln's Emancipation Proclamation may have soothed the abolitionists, but it fanned antiwar fervor, and Lincoln was a Republican. In the north, Peace Democrats were determined to fill the governorships and stop the war at the ballot box. The loss of one state meant the loss of one state's army to the Union cause.

During the spring of 1863, Anna Dickinson's luck drastically changed when Benjamin Franklin Prescott, the secretary of New Hampshire's Republican Committee, requested her assistance in the upcoming political campaign. Deeply moved by "Hospital Life," he believed that her charisma and eloquence could serve the Republicans in the upcoming gubernatorial election. Dickinson quickly exhibited persuasive skills in politics. "Her audiences are held as though they were electrified," wrote a local journalist. One of the first women to speak publicly on political issues, her characteristic pathos and wit was just what the Republicans needed to win in New Hampshire. The election was close and the governor-elect was sure that he owed his triumph to the young Miss Dickinson.

Because of her phenomenal success, she was whisked to Connecticut. Her first speech in Hartford was reported in Charles Dudley Warner's Press the following morning:

The Hall, which was comfortably filled at the beginning of the address, was packed as we never saw it as the evening went on. And the audience, which began to listen in a quiet, half-critical manner, soon lost control of itself under the witchery of such a spell as a Hartford audience was never under before…. She spoke rapidly, her ideas evi dently outrunning even her lightning-like utterance, memory and imagination both crowding her…. In certain powers as a speaker we have never heard her excelled.

Somewhat alarmed by Dickinson's unexpected accomplishment in New Hampshire, Democrats endeavored to sabotage her speeches. Undaunted, she often capitalized on these diversions. When the lights were sabotaged in one hall and audience and speaker were pitched into temporary darkness, Dickinson sang out: "I see that there are those here who evidently love darkness better than light, because their deeds are evil." In another instance, the Democrats stood outside yelling "Fire!" while a fire engine clanged up the street. "Yes, there is a fire," retorted Dickinson, "we have kindled a fire, which these people by their acts are assisting, that will never go out" until nothing is left of the Democrats, "save ashes." The Hartford Courant, a leading newspaper, extolled her closing speech of the Connecticut campaign; its headline dubbed Dickinson, "THE MOST REMARKABLE WOMAN OF THE AGE." This description was not inaccurate; the Republicans credited their sweeping and unexpected victory to Dickinson's oratorical abilities. Officials presented her with a gold watch, $100 for every night that she spoke, plus $400 for the closing speech. Within two years of her first speech, Anna's eloquence, passion, and persuasive talent had achieved notoriety throughout the country.

Inspired by her accomplishments, the Republicans beseeched Dickinson to speak at Cooper Union in New York. Her popularity preceded her—over 5,000 crammed into the hall, and many more were sent away. One account of her speech was printed in The New York Times:

She sways the audience from the first moment of her electric utterance down to the last syllable of the ten thousand words which she must have spoken in one short hour. She is a walking encyclopedia of the events of the war, with all the pages open to you at a glance. She heaps history, fact, proverb, warning, story, appeal, and exhortation in convincing array, sweeping all before her in an avalanche of intellectual force.

As in the other states, a Republican victory followed. Once again, the party did not hesitate to credit Anna with the success; for her eloquent oratory in New York, she received $1,000 plus a request to deliver the same speech in Philadelphia. With the money, she rented a commodious house for her family, paid the bills, bought gifts for friends, donated to charities, and purchased a new wardrobe. "In her zeal to give to others," Anna "often gave more than she could afford," writes her biographer Giraud Chester.

Reformers were ecstatic with her success because her popularity gained support for the abolitionist cause. In turn, women's rights activists emphasized her importance as a pioneer; her triumphs in politics and public speaking forced society to reexamine the limited roles that women were impelled to assume. "I am thoroughly satisfied with this noble girl," commented Eliza-beth Cady Stanton . "How many life-long hopes and prayers I realized as I listened to her eloquence." As a result of her youth, passionate convictions, and effect upon audiences, many people proclaimed Dickinson the American Joan of Arc.

Anna Dickinson attracted the attention of the press for a variety of reasons. Curious, the multitude initially flocked to see her because of her age and gender, but soon she became renowned and respected for her style. Many were impressed that she spoke extemporaneously. She generally had only a few notes scribbled on a scrap of paper. Although Democratic newspapers sporadically mocked Dickinson and called her "unsexed," most journalists praised her for her style and unique charismatic appeal. Petite, with penetrating blue eyes, and short, shiny, curling black hair, Anna's appearance and simple dress were pleasing. The Boston Commonwealth commented: "[I]n these days when women seem to have gone insane" adhering to fads that 'torture' and 'disfigure,' wearing 'corsets, crinolines and trailing skirts,' it is singularly refreshing to see a woman who entirely understands the art of dress. And that woman is Anna Dickinson."

Dickinson's most impressive feature, however, was her deep, rich voice and speaking style. "She was an orator to remember," writes Chester. "Her rich, vibrant voice carried to every corner of the chamber without obvious effort, yet when she dropped it to underscore an impelling point, its grim intensity made it audible to every listener. Her poise was manifest and her earnestness overwhelming. Each word bore the stamp of conviction, as if she was prepared to stake her life upon its truth." In the traditional praise-one-woman-by-disparaging-the-rest, the New York Independent wrote that, unlike other female orators, "Miss Dickinson is not a woman speaking like a man," and by maintaining femininity "she proves beyond all controversy that there are elements of truth, and phases of public affairs, … that can be given from no standpoint than the heart of a true woman." Many prominent men proposed matrimony to Dickinson, but Whitelaw Reid, a leading journalist for the New York Tribune, seemed to be the man most likely to marry her. The press often linked the couple's names, and for a time Reid frequented the Dickinson home. Though the two maintained a close friendship for a number of years, they became badly estranged in the 1870s. Despite the many proposals, Dickinson chose not to marry.

During the fall of 1863, the Republicans entreated her to lecture throughout the coal-mining towns of Pennsylvania, places known to be dangerous. Since the majority of the working class in this area vehemently opposed the Republicans and the conscription laws, rioting often occurred. But the Pennsylvania Republicans viewed Anna, who had been part of the working-class and sympathized with their concerns, as their only chance at victory. Officials offered her $12,000 to lecture for 12 days where no male speaker dared to tread. Agreeing, Dickinson occasionally encountered violence firsthand. Before delivering one speech, a disgruntled man shot at her; the bullet actually cut off a lock of her hair. Seemingly undaunted, she began to speak, and, impressed by her courage, the miners listened to her lecture. On the next stop, when met with loud hisses by one gentleman, she replied: "I know of but two animals that use that mode of expressing themselves, the goose and the snake. If you, sir, can sit and listen to falsehoods in a Democratic meeting, and cannot listen to plain facts now, use the mode of locomotion designed by nature for your kind, and get down and wriggle out!" Reported the Pottsville Miner's Journal: "Not another hiss was heard." After this tour, the Republicans in Pennsylvania were victorious. Although they showered her liberally with praise and once again credited the success with her speaking, Dickinson never received the promised $12,000. From that time on, she insisted on signed contracts, but the erosion in trust in political friends would take its toll.

Dickinson continued to lecture in upstate New York, then New England and Chicago. After completing these tours, she was invited to Washington D.C. to address Congress. At first, it was to be in a local theater with Congressmen attending, but Dickinson would only agree if it was an official invitation to the Hall of Representatives. Even though no woman had ever been invited to speak there, Anna stuck to her terms. On January 16, 1864, in the House of Representatives, in a speech intended to sway Republican opponents, she attacked Southern secessionists, Democrats, the Supreme Court for the Dred Scott verdict, and President Abraham Lincoln himself for his December Amnesty Proclamation. By the end of the lecture, she had turned her criticism into a passionate demand for Lincoln's re-election. The press was ecstatic, calling "the young Quakeress" a genius. Whitelaw Reid wrote in the Cincinnati Gazette:

Washington has witnessed strange scenes, betokening strange changes, in the last two years, but I can recall none so strange as that witnessed in the Hall of the House of Representatives last Saturday night. Before the largest and most distinguished audience ever assembled there, there came a young Quaker girl, eight months before a humble employee of the mint, tonight the bravest advocate for the integrity of the Republic and the demand for universal liberty throughout it. Her success has been the most remarkable won at the capitol.

However, throughout the year her opinion vacillated, and, after publicly condemning the president, she was compelled to support him after the Democrats nominated her enemy, McClelland. (Dickinson quipped that she agreed with the little old lady who stuck up for the Civil War general: "Why will the people keep attacking poor, dear, little George McClellan? I'm sure he never attacked anybody.") Though still popular, these seemingly unmotivated oscillations disturbed fellow abolitionists and signaled the first of a series of actions that alienated Anna from a few reformers.

After Lincoln's re-election, Dickinson became an integral addition to the lyceum circuit. At that time, the public speeches held in various lyceums across the country provided a form of entertainment and informed the populace about contemporary news. For nearly five years, Dickinson toured the South, Midwest, and West, delivering speeches on issues of social reform almost every day. Because the Republican success enhanced her popularity, she often earned an annual salary of over $20,000, an extraordinary income for any American at that time. She was at the top of the ladder, "rivaled by only one or two men," wrote Chester.

Anna was rich on her own earnings; she was beholden to no man; she would not be shackled by Victorian rectitude or the vestments of tradition. In an era when propriety seemingly was the foremost of virtues, she recognized no master save her impulses and her means. She was blatantly and self-consciously nonconformist, and seemed to take delight only in asserting her individuality and refusing to accept without question or protest the code of behavior that shaped the lives of her contemporaries. She dressed as she desired; she traveled where and how she willed; she delivered lectures on subjects many people felt should not even be mentioned in the presence of unmarried young ladies. As a result, she antagonized many of her former friends and supporters. Conservative newspapers now began to find fault with her and even to ridicule some of her habits and beliefs.

After encountering Mormonism in the West, her speeches often criticized polygamy, an "unmitigated despotism," which she felt stifled and degraded women.

In 1866, Dickinson met with Frederick Douglass, the celebrated abolitionist, and Theodore Tilton, editor of the Independent; the three formulated a Constitutional amendment that would prohibit disenfranchisement on account of race, color, or sex. As politicians revised the idea, however, the word "sex" was lost. When ratified four years later, the 15th amendment provided suffrage to men of all races, but excluded women, idiots, and criminals. Although Dickinson promoted the equality of women and maintained a friendship with Anthony and Stanton, she declined active participation within the suffrage movement.

Throughout, Dickinson dealt with frequent bouts of bronchitis, forcing her to remain in bed in strange hotels, sometimes for weeks. She also endured swings of high energy and deep depression. Having once again crossed paths with her on a lecture tour, Susan B. Anthony commented, "I found her the most weary and worn I had ever seen her, and desperately tired of the lecture field." Dickinson had peaked as an orator and political pundit, the natural next step was seeking a political life, but that was barred to her because of her gender. "An unmarried woman who must live by her labors and can expect no political office," said Dickinson, "needs to look to matters of money."

In the 1870s, the popularity of the lyceum circuit declined in America, and, tired of constant traveling, Dickinson embarked upon a new career as an author. Her first novel What Answer? attacked the problem of racism in American culture by defending the marriage of an interracial couple. The book was more of a social commentary than fictional work, and some critics challenged her creative ability. Respected reformer Harriet Beecher Stowe wrote to her, praising her labors: "Well done, good and faithful Anna…. don't mind what anybody says about it as a work of art. Works of art be hanged! You had a braver thought than that." Dickinson likely appreciated this comment because her personal life was undergoing upheaval. Despite her considerable income, the Dickinsons were, once again, on the verge of penury. Anna's extravagance in gifts and charitable donations, and her sister Susan's poor monetary management, steadily drained any savings. In addition, their brother Samuel passed away and Edwin became severely ill. With hospital bills and debts mounting, Dickinson resumed lecturing.

During the presidential campaign of 1872, her expert oratory was sought by both the Republicans and Democrats. The former, with whom she had achieved unprecedented popularity, offered her $20,000, while the latter proposed only half that amount. Despite her previously successful affiliation with the Republicans and the larger salary, Dickinson decided to campaign for the newly formed third party, the Liberal Republican Party, and its nominee Horace Greeley, famed editor of the New York Tribune, because she deplored the corruption and nepotism of the Grant administration. In spite of her vehement attack of Ulysses Grant, the Republicans won in a landslide victory. Gradually, Dickinson realized that her affiliation with the Democrats, who had backed Greeley, had damaged her career. Because Greeley refused to endorse women's rights, and the Republicans had a plank in their platform stating that the party was "mindful of its obligations to women," she had alienated herself from some suffragists. Furthermore, by endorsing Greeley, she disappointed many reformers and forfeited over $5,000 from cancelled lectures. She had lost much sympathy with the press who now began to demand that she "get married."

Her association with Greeley was not the only reason for cancelled lectures and a decline in popularity. While delivering a speech about "Demagogues and Workingmen" during 1871–72, Dickinson assailed industrial corporations and, in so doing, earned their disdain. In the same speech, however, she attacked trade unions and opposed the eight-hour day, and irreparably estranged the working class, who had always seen her as a hero. Antagonizing both groups also reduced her lecturing schedule and diminished her popularity. Likely disappointed by the turn of events and unaccustomed to being shunned from the limelight, Dickinson's health rapidly deteriorated. Her family was forced to move from their extravagant home to the small town of West Pittston, Pennsylvania. Desperately in need of employment, Dickinson turned again to lecturing. During 1873–74, she provided eloquent discourses about the problem of prostitution. Though she displayed remarkable insight into the problem, a woman lecturing about prostitution shocked the 19th-century code of propriety. The Philadelphia Inquirer advised "all respectable people to remain away" from her speeches.

After delivering a few unprofitable lectures, she wrote a second novel. A Paying Investment, another social commentary, demanded compulsory education, examined the roles of citizenship, and emphasized the civic responsibility to vote. Though reformers praised the text, it was not a financial success, and, Dickinson, at 30, turned to a career in the theater. Because Quakers considered the theater a vice, she risked severe maternal disapproval. In May 1876, she made her stage debut in Boston, starring in the title role of the play she had written, Crown of Thorns or, Anne Boleyn. Though reviews in Boston were somewhat encouraging, the New York critics were severe, ridiculing not only Dickinson's acting ability, but the script itself; the play closed after a brief continental tour.

Following the failure of Crown of Thorns, Anna wrote a handful of other plays that were not performed. In 1879, she wrote her final published novel, A Ragged Register (of People Places and Opinions). Though the text provides an interesting, select account of Dickinson's speaking experiences, it did not become the success she had imagined. Undaunted and in need of income, within a year she produced another play. American Girl, the first performance in which Dickinson did not star, became her most popular production. With celebrated actress Fanny Davenport playing the lead, the play enjoyed modest success in 1880 and received encouraging reviews. Theatrical victory, however, was ephemeral. Following a clash of egos between Dickinson and Davenport, performances ceased; Dickinson continued writing plays, but she could not produce them.

After a brief hiatus, in 1881 38-year-old Dickinson attempted to resume her acting career. This time, she shocked audiences by playing traditional male roles, such as Hamlet; as with her former sojourn in the theater, reviews were mixed. After nearly four years of touring the country with occasional dramatic work, Dickinson lost most of her belongings in a fire; she returned to stay with her mother and sister in West Pittston.

In 1888, the Republican National Committee requested that Dickinson speak on their behalf during the upcoming presidential campaign; nearly broke and bored, she quickly consented. As in previous years, her eloquent speeches proved immediately successful in Indiana and Michigan. Unfortunately, her popularity dwindled somewhat when she vehemently attacked Grover Cleveland. As she railed against the "the hangman of Buffalo," some questioned her reasoning. She proceeded to New York, but after only a limited number of speeches, her role in the campaign deteriorated. Frustrated, she returned to her family at West Pittston. Within months, her mother, who had been ill, died. Feeling stifled and out of place in the small community, Dickinson's health deteriorated both physically and mentally. Throughout her life, she had sporadically suffered from a frail constitution; now, she was seized with unbearable headaches. Rumors circulated throughout the town that she was an alcoholic, and, over time, her eccentric behavior was identified by locals as paranoia. After a reported confrontation with her sister, Dickinson was taken to the Danville State Hospital for the Insane.

After five weeks, she was re-evaluated by a different doctor and released. Befriended by this physician and his wife, she relocated to their home in Goshen, New York. Immediately following her release, she brought litigation against her sister and the doctor responsible for her commitment. The trial, held in 1895, resulted in a hung jury: two years later, the case was retried. Although Dickinson was found unquestionably sane, she was awarded only six and one-quarter cents and held responsible for court costs that were over $3,500. However, she did collect some compensation from a libel suit against the New York newspapers; in addition, the $25,000 lawsuit against the physician who had committed Dickinson to Danville was settled out of court. Dickinson lived to be nearly 90, spending the last 40 years of her life peacefully in New York. Though she continued writing plays, these were never published. Outliving most of her contemporaries, she faced obscurity and often reminisced over old newspaper clippings and letters. She died in Goshen six days before her 90th birthday. Though the new generation did not realize how Anna Dickinson's passionate speeches had expanded their role, all women are indebted to her; for her actions helped dismantle the cultural ideals that restricted women who spoke in public.