When the Going Was Good: An Editor's Adventures During the Last Golden Age of Magazines

When the Going Was Good: An Editor’s Adventures During the Last Golden Age of Magazines is a memoir by Canadian journalist and editor Graydon Carter. Originally published in 2025, When the Going Was Good traces Carter’s life from his humble Canadian upbringing through his high-powered tenure as the editor-in-chief of Vanity Fair. Carter writes from the first person point of view and incorporates anecdotes and wit into his renderings of 1990s and 2000s New York culture. The memoir explores themes including the Evolution of Print Journalism in the Digital Era, the Entanglement of Success, Celebrity, and Power, and the Media’s Impact on the Political and Cultural Narrative.

This study guide refers to the 2025 Penguin Press hardback edition of the memoir.

Content Warning: The source text and guide include depictions of graphic violence, sexual harassment, drug use, alcohol consumption, and themes of death and loss.

Summary

Graydon Carter sets out to recount the story of his adventures in the publishing world. He does so by detailing his childhood in Canada and his early dreams of moving to New York. As a young boy, Carter didn’t know what he wanted to be when he grew up. He was an average student, had average looks, and an average personality. However, he did develop an early love for reading and hockey.

After Carter finished high school, he took a six-month gig with the Canadian Railway. Carter liked the job despite its challenges, but quickly realized that he wanted a more glamorous lifestyle. Once he finished this job, he started taking classes at the University of Ottawa. He didn’t focus on his coursework and instead focused his attention on co-founding The Canadian Review. Carter loved the magazine and was thrilled by its success. However, the magazine struggled financially and soon folded.

After his time with the Review, Carter pursued a publishing program at Sarah Lawrence in New York. Through the program, he secured a job at Time as a floater. He moved between departments, trying to work hard and prove himself. He then worked for Life, a now tired publication struggling to keep up with the television industry. Seeking a more vibrant working environment, Carter founded Spy magazine with his friend and colleague Kurt Andersen. Spy was a monthly publication that satirized the New York wealthy and elite—and particularly targeted the Vanity Fair culture. The magazine did well, but Carter eventually left to revitalize the dying Observer newspaper.

While Carter was at The Observer, Condé Nast owner Si Newhouse asked Carter to step in as editor of The New Yorker. Carter accepted, but Si ended up giving the position to another editor. Instead, Si told Carter he could step in as the editor of Vanity Fair. The magazine had folded in 1936 and Si was trying to resurrect it.

Carter was flattered by Si’s trust in him but also worried about earning the respect of his new colleagues. It took time for him to orient to the high-profile Condé Nast realm and to establish trust with the Vanity Fair team. However, he soon reinvented the company culture—firing toxic team members and hiring new writers and editors. He lists all of the positive relationships he had during his time with the magazine, and details how each of these individuals impacted him personally.

Carter reflects on his work with Vanity Fair. He again notes how nervous he was about letting Si down and losing his job. However, he also acknowledges how much he learned and grew while there. He particularly underscores the importance of his friends and mentors at the time. He also details his biggest accomplishments with the magazine—most notably, starting the Vanity Fair Oscars party in Hollywood. In 1993, Carter felt that Hollywood was forgetting its romantic history. With Vanity Fair, he started to host an after-party on Oscars weekend defined by an elite guest list, elaborate decorations and venues, and surprising party favors. Carter holds that he and Vanity Fair are responsible for renewing Hollywood’s glamour.

Carter is also proud of how he changed the face of Vanity Fair. He incorporated more political stories, determined to make amends for the magazine’s failure to properly document the events leading up to World War II in Europe. In particular, Carter featured in-depth reportage on the 9/11 al-Qaeda terrorist attacks and the 2008 Great Recession. (Outside of Vanity Fair, Carter was also broadening his cultural reach via making documentaries on important cultural figures and historical events.)

Carter made the decision to leave Vanity Fair in 2017 when Anna Wintour pushed for Condé Nast to restructure the company. Carter disagreed with her decision because it didn’t align with his editorial ethos or standards. Although the decision to retire was difficult, Carter is glad that he left when he did. He is also grateful for his trusted colleagues’ assistance in a seamless transition. Since his retirement, he has launched and been running the online publication Air Mail. He acknowledges the challenges of this work, but also holds that Air Mail is a testament to his love for editing.

In closing, Carter offers his reader a series of lessons he learned from his time in the magazine industry. He gives advice on establishing healthy relationships, taking oneself seriously, and enjoying life to the fullest.