In 1935, Dempsey moved to Toronto, briefly working at the Star Weekly, before being hired by Chatelaine Magazine as assistant editor.

[4] The store eventually grew into a full grocery and Lotta worked with her father assisting customers, washing fruits and vegetables, stocking shelves, and sometimes making deliveries.

[17] The women's section typically covered social and charity events, household tips, recipes, clothing, and prominent personalities.

Despite not being allowed to write hard news stories, Dempsey was happy to be working as a reporter,[11] but after four years, she was offered CA$40 per week at the Edmonton Bulletin.

[11][18] The salary was very high, particularly for a woman at that time, and she was offered the opportunity to cover more newsworthy events and travel, prompting her to change jobs.

She was assigned to cover Vancouver and Winnipeg, and wrote stories about education, trappers and traders, First Nations reserves, and Mennonite settlements.

[11] Wanting to improve her skill, in 1929, Dempsey asked Charlie Campbell, her publisher, for six weeks off to take a journalism class at Columbia University.

He set up an itinerary from among his friends which included stops at the Seattle Post-Intelligencer, The Oregonian in Portland, The San Francisco News and the Los Angeles Herald Examiner.

[17][19] Activists like Henrietta Edwards, Nellie McClung, Emily Murphy, and Irene Parlby taught her that covering issues like addiction, child abuse, and domestic violence were necessary for her to become a "good reporter, and more important, a worthwhile human being".

[21] Given a CA$500 bonus by Campbell for staying with the paper during the worst of the depression, Dempsey made plans to move to Toronto.

[11] She wrote for the magazine under numerous pseudonyms, using John Alexander for features, Carolyn Damon for fashion, and Annabel Lee for beauty pieces.

[2][11] Within a few months, she met the architect Richard "Dick" Fisher, a young father of two boys,[11] and they married on 5 December 1936 at Hart House chapel at the University of Toronto.

[25] On deciding to return to work, Dempsey hired a gay houseman named Stanley Burrows, who bought and cooked the meals, decorated their home with flowers, and did the chores and gardening.

[27][28] Dempsey returned to Chatelaine in 1944, as the women's page editor,[11] and the family moved to a new home on Woodlawn Avenue near her office.

[29] Her style of editing went beyond the usual sphere of the home and encouraged Canadian women to learn about and be involved in the broader issues affecting the country.

The managing editor had wanted to be editor-in-chief and frequently undermined Dempsey, who did not enjoy all the administrative tasks associated with the top editorial post at the magazine.

[47] She also met and wrote about Jacqueline and John F. Kennedy, and Pierre Trudeau, as well as celebrities such as Humphrey Bogart, Noël Coward,[2] and Lorne Greene.

[50] Around the same time, Dempsey used a situation, which occurred when her managing editor Charles Templeton asked her to take his daughter to the restroom, to drive the point home that women's washrooms were still not available on the floor where the editorial staff worked.

When the East-West Summit planned between Dwight Eisenhower and Khrushchev was cancelled in 1960 after a US U-2 plane was shot down in Soviet air space, Dempsey wrote a series of columns about what women could do to calm Cold War tensions.

[53] Dempsey was a founding member of the organization,[17] supporting its efforts and those of other activists to ban nuclear weapons and prevent war.

[58] Despite her years of writing, Dempsey was never promoted to a more prestigious reporting position than her general interest column and never became a senior manager for a newspaper.

[62][63] The book told her life story with her typical humour, relaying missteps she had made, encounters with royalty and celebrities, and memorable world events that occurred during her career.

[27][64] Reviews by journalists Alsop of The Province, Eleanor Callaghan of the Montreal Star, and Judy Creighton of The Canadian Press, all commented on Dempsey's ability to laugh at herself, her honesty about the notables she liked and disliked, and her portrayal of journalism as a career in her era.

[66] The hosts presented information on useful topics including cooking, pensions, and staying active, but also practical issues such as loneliness and loss.