Like all of us, Cosmopolitan magazine’s longtime editor Helen Gurley Brown lived with conflicting drives and desires. But Gurley Brown’s ideas and insecurities had a public platform, where she championed sex for singles while downplaying workplace sexual harassment and featured feminist voices while upholding the beauty ideals that made her own life difficult.

A workhorse who played hard, Gurley Brown, who died in 2012, is presented as an often contradictory heroine and an unexpected success story in journalist Gerri Hirshey’s new 500-page biography, Not Pretty Enough: The Unlikely Triumph of Helen Gurley Brown.

Helen Gurley Brown’s life and example—almost a classic Horatio Alger “rags to riches” tale—affirms that the American idea of surmounting humble origins is sometimes possible, if improbable. But Gurley Brown’s story also illustrates both personal grit and endurance. Wily, willing to take risks, and sexually audacious, she might be a questionable role model for 21st century women, but her amazing story, as told by Hirshey, will nonetheless inspire and entertain.

Born in 1922, Gurley Brown led Cosmopolitan for 32 years. She moved the magazine, which had been published continuously since 1886, from relative obscurity into the limelight. Known for its brash cover chatter and how-to articles on heterosexual man-pleasing, Cosmo is the world’s highest-selling women’s magazine, with 61 print editions. Its long history—alongside Helen Gurley Brown’s personal story—offers a fascinating window into the intersection between U.S. publishing and burgeoning 20th-century feminist ideologies.

Hirshey (whose earlier books include Nowhere to Run: The Story of Soul Music and We Gotta Get Out of This Place: The True, Tough Story of Women in Rock) presents Gurley Brown as a mess of pushes and pulls: insecure, brilliant, bold, self-effacing, loyal, independent, jittery, and frugal to the point of deprivation. Indeed, Hirshey’s revealing and detailed biography describes the pioneering editor as someone hungry for experiences; a sophisticated New Yorker with deep roots in rural America; and a writer of guidebooks who had trouble taking advice. In short, Helen Gurley Brown was limited by a host of personal issues, but that did not stop her from trying to push societal boundaries and shatter sexual propriety.

A native of small-town Arkansas, Helen’s childhood was marred by tragedy. Her father died in an accident when she was 10; several years later, her older sister, Mary, contracted polio, which left her partially paralyzed. Helen’s mother, Cleo, was overwhelmed and often depressed. Nonetheless, she scrambled to keep the creditors at bay, and the family lived in numerous decrepit rentals during Helen’s childhood.

Poverty was not the only obstacle Helen faced. According to Hirshey, “By the time Mary and Helen were school age, Cleo had begun her steady warnings that pretty girls got the best in life.” While Cleo never used the word “plain” to describe her offspring, it was clear that she did not think them comely. Helen was devastated. What’s more, the fear of being unattractive dogged her for her entire life and she had multiple surgeries to correct “flaws.” She also starved herself and exercised compulsively—and would likely now be labeled as having an eating disorder—to keep her weight at an unwavering 105 pounds.

Her success, Hirshey writes, was the result of luck, tenacity, and sheer chutzpah.

It started in the 1940s, shortly after she finished high school and secured the first of a string of secretarial jobs. During her tenure as a typist and stenographer, Helen cozied up to her male bosses and slept with some of them.

“It was the first time she truly observed and understood that sex is power,” Hirshey writes. “Helen had come to realize that sex was a surprising and thrilling equalizer between the sheets.” Gurley Brown pooh-poohed the idea that people should wait until marriage to have sex and had no problem dating men who were cheating on their wives. The same went, Hirshey writes, for racists and overt anti-Semites. Since she was giving a large part of her earnings to her mother and her sister, it was the size of a man’s bank book, rather than his politics, that evidently curried her favor.

Nevertheless, being a mistress had a downside, and Helen’s diary reveals that she felt like a “little bird … expected to stay in her cage, always available yet always alone.”

Her fortunes turned shortly after her 26th birthday, when she became secretary to Don Belding, chairman of the board at prestigious ad agency Foote, Cone, and Belding. Belding paid Helen $75 a week and treated her like a long-lost daughter; she considered him a surrogate father.

Alice Belding, Don’s wife, took a particular interest in Helen and, after reading something she’d written, persuaded her husband to give Helen a chance as a copywriter. He did, making her one of the first women to break into the field.

Meanwhile, there were men. Lots of men. “Certainly, men love beautiful women,” Hirshey writes. But Helen realized that when “the lights went out, Miss Universe might just as well be the poor, sooty match girl if she couldn’t make him shout hallelujah.” She loved the power sex gave her, but was hurt during a group therapy session when another participant dubbed her a slut. “Spoken with venom, it had the effect of a gut-punch,” Hirshey writes.  Still, it proved clarifying for Helen, allowing her to formulate the idea at the heart of her 1962 book, Sex and the Single Girl: There is nothing shameful about unmarried people having sex as long as it’s consensual.

Helen met David Brown, a high-profile movie executive, in 1958, when she was 36. David was 42, twice married and twice divorced, and had no interest in returning to the altar anytime soon.  This was fine with Helen. Nonetheless, as they spent more and more time together, they formed a strategic partnership. Yes, there was love, but Helen Gurley craved financial security, which David could provide. They wed in September 1959.

At that point, David suggested that Helen take a professional detour and write “a guidebook of sorts for single women.” Hirshey reports that he envisioned “something along the lines of ‘How to Have a Successful Affair’” and ticked off possible subjects, including how to snare a guy and dress for conquest. He also wanted the manual to include concrete sex tips. Helen loved the idea and the pair began to work on it, she as writer, he as editor.

Sex and the Single Girl told the truth as Helen saw it. Hirshey notes that the book was meant as a practicum, “and was never intended as an overtly feminist tract. Systemic change was not at all on her radar; she addressed herself to bettering the small, quotidian lives toiling within the status quo, of those, herself included, she would come to call ‘mouseburgers.’ Sexism was not even in her vocabulary.”

Her message was quite simple: Sex needed to be decoupled from marriage. As for gender roles, she was fine with women playing coy. In fact, she explicitly advised women to go out with men only if they could pay for everything, from dinner and drinks to “prezzies.”

There were of course, detractors, but Sex and the Single Girl sold millions of copies and made Helen Gurley Brown a household name. She appeared on countless TV talk shows and was the first woman featured in Playboy’s famous centerpiece interviews.

In the throes of her success, however, David was offered a job in New York and the couple decided to leave California, where they’d both lived for decades. David, Hirshey reports, knew that Helen needed to work, “that Helen unemployed would be Helen unhinged.” Together, they developed a prototype for a monthly women’s magazine that would popularize and expand upon the ideas in Sex and the Single Girl. They called it Femme and floated the idea to every publisher they knew. No one liked it.

Eventually, Hearst Corporation suggested “superimposing” the format on one of the corporation’s least successful publications, Cosmopolitan, with Helen Gurley Brown at the helm.

It worked, not only boosting sagging sales but catapulting “The Cosmo Girl” to prominence. Sexual freedom, Gurley Brown enthused, was in–but apparently only for heterosexuals, since the magazine rarely acknowledged the existence of same-sex relationships or bisexuality.

Nonetheless, the first few issues tackled then-risqué themes, as these titles suggest: “The Bugaboo of Male Impotence”; “I was a Nude Model (and This is What Happened)”; “Things I’ll Never Do with a Man Again”; “The Astonishingly Frank Diary of an Unfaithful Wife”; and “How to Make a Small Bosom Amount to Something.”

As the “sexual revolution” of the 1960s took hold, Cosmo flourished, albeit steering clear of covering racial unrest, the Vietnam War, or the counterculture and anti-militarism movements. Likewise, if Gurley Brown had any thoughts about the civil rights or peace movements, Hirshey neglects to mention them. She does note that for Helen, “readers of color scarcely registered.” It’s too bad this is not probed more deeply in Not Pretty Enough, and why the editor remained above the fray—was it fear, disinterest, or hostility?—remains unclear.

The women’s movement of the 1960s and 1970s did capture Helen’s interest, though, and she considered herself a devout feminist, with a particular passion for promoting reproductive rights. She wrote numerous articles about the need to overhaul abortion policies pre-Roe v. Wade, openly declaring that “it’s a shame that girls have to go to Mexico or Europe to be operated on.” At Cosmo, she cheered the arrival of the birth control pill in 1960; hailed the 1965 Supreme Court decision in Griswold v. Connecticut that gave married heterosexuals access to birth control; and was exuberant when Eisenstadt v. Baird gave unmarried couples the same right to control their fertility in 1972.

Sexual harassment, on the other hand, was befuddling to her. Remembering her days as a secretary, she dubbed slaps on the ass and sexually suggestive comments to be harmless fun. “When a man finds you sexually attractive, he is paying you a compliment,” she wrote in a monthly Cosmo column. “When he doesn’t, that’s when you have to worry.”

Small wonder that Kate Millett picketed Cosmo for its “reactionary politics” or that Betty Friedan slammed it for its sexism and preponderance of inane articles on keeping men happy.

Despite disagreeing with these thinkers, Helen Gurley Brown marched down New York City’s Fifth Avenue to celebrate the 50th anniversary of women’s suffrage in August 1970 and published articles written by prominent feminists as the 1970s unfolded.

Then, at the height of the AIDS crisis, Gurley Brown stepped in it. In early 1988, Cosmo ran an article that minimized the possibility of heterosexual transmission of HIV and made it sound as if straight women were immune from infection. Equally horrifying, the author, psychiatrist Dr. Robert E. Gould, was overtly racist. “Many men in Africa take their women in a brutal way,” he wrote, “so that some heterosexual activity regarded as normal by them would be close to rape by our standards.”

Oy. Readers were aghast, and Gurley Brown was roundly and deservedly criticized. Even Surgeon General C. Everett Koop weighed in, saying the article did “such a disservice” by suggesting that the risk of contracting the virus was low for heterosexual women. Hirshey reports that, inexplicably, the article was never retracted or corrected.

By this point, however, Helen was showing signs of dementia—she had periodical temper tantrums in public and was becoming less reliable and sharp—so Hearst Corporation brought in several new editors, albeit without firing Helen. She continued going into the office until shortly before her 2012 death. She had done paid work for 71 years.

Hirshey’s sources range from primary documents and in-person interviews with people who knew Gurley Brown, including Gloria Vanderbilt and Barbara Walters. Correspondence and recorded talks between her and friends such as Jacqueline Susann and Joan Rivers provide incisive, funny, and poignant anecdotes. These interviews give the book reportorial gravitas and intimacy. And although Hirshey had only a passing acquaintance with her subject—she had interviewed Gurley Brown decades earlier for an article about marriage proposals—she nonetheless manages to show Gurley Brown as a regular Jane who spoke openly about her nagging doubts.

Many readers will feel as if they can relate to Gurley Brown’s struggles and triumphs. Throughout the book, I felt sad for her, but also wished we’d met.

In fact, I closed the book wanting more; among other things, I wanted to better understand what it was like for her to move between near-poverty and the upper crust. Did she feel like an impostor? Did her lifelong conviction that she was not pretty enough or smart enough keep her from feeling connected to others? Did she ever feel truly secure?

Perhaps Gurley Brown’s self-doubts are what kept her from becoming arrogant or abusive to others; even those who hated Cosmopolitan or were frustrated by her racial and political blind spots admired her kindness. Similarly, these doubts did not prompt her to disguise her eccentricities—among them, pilfering from petty cash and always taking public transportation rather than cabs. Indeed, whatever Gurley Brown felt about her own appeal, Hirshey’s biography presents Helen Gurley Brown the woman as quirky, humble, and utterly fascinating.