Last week, I had the privilege of watching ABC anchor Diane Sawyer moderate a conversation between Supreme Court Justice Ruth Bader Ginsburg and former Supreme Court Justice Sandra Day O'Connor. The extraordinary coffee klatch was part of The Women's Conference, a mega-watt, multi-day convention hosted by Maria Shriver. With her uber Kennedy-Schwarzenegger sphere of influence, Ms. Shriver has become the George Clooney of women's events. She can lasso some of the country's most fascinating female leaders and celebrity role models -- think Oprah and Michelle Obama -- to speak at her annual festival of jacked-up Girl Power.
Sitting in an estrogen-packed auditorium with 14,000 other women (and a few token guys, including NBC's male Dream Team: Matt Lauer, Brian Williams and Al Roker), I listened as two of the most influential and extraordinary women of our time spoke about the struggles and in-your-face discrimination they experienced as they ascended the ranks from law school to the Supreme Court.
Sandra Day O'Connor's story makes for feminist folklore. The Stanford law school graduate couldn't get a job when she graduated in 1949. She sent out dozens of resumes only to be told, "We don't hire women lawyers. How well do you type?" Eventually, through a family friend, Ms. O'Connor interviewed with the county attorney's office in San Mateo, California, where she actually offered to work for free. She got the gig, but if working for bupkis didn't marginalize her enough, Ms. O'Connor was also forced to sit with the secretaries.
A few years later, across the country, newly married Ruth Bader Ginsburg had ambitions of going to law school. She had taken her LSATs and applied to Harvard. But then she got pregnant and thought she may have to quash her law school plans. As she agonized, it was Ms. Ginsburg's father-in-law who set her straight and told her, "You have the best excuse in the world now not to go to law school, but if you want to go, you'll figure it out."
So Ms. Ginsberg chose to man-up in a man's world and take on Harvard Law School while raising a baby. She was one of nine women in a class of 500.
Like Ms. O'Connor, Ms. Ginsberg found that having a uterus was a big-time job impediment. No one wanted to interview her. And despite her credentials and a strong recommendation from the dean of Harvard Law School, Ms. Ginsberg was denied a clerkship for Justice Felix Frankfurter because she was a woman.
Five decades later, the cultural landscape has significantly shifted. Today, there are more women in law school than there are men. We have a female Secretary of State and a female Speaker of the House and dozens of women in Congress. Women are no longer a novelty in politics but a permanent fixture -- witches, Mama Grizzlies and all. And two more women, courtesy of the Obama administration, have joined the Supreme Court's growing sorority: Elena Kagan and Sonia Sotomayor.
When Diane Sawyer asked the justices, "How many women are enough on the court?" Ginsburg replied, without missing a beat, "Nine. There have been nine men there for a long time, so why not nine women?"
Then, after a boxed lunch of couscous and chicken salad, in a cultural whiplash, the conversation swung from the Supreme Court's judicial giants to the supermarket stardom of Jessica Simpson. The platinum blonde, best known for her Daisy Dukes, failed relationships and burgeoning clothing line, joined a panel to speak about empowering young women with self-esteem.
The irony was not lost on anyone.
So while we women stand on the shoulders of Justice O'Connor and Justice Ginsburg because they broke down barriers, we also stand at the checkout line staring at Jessica Simpson's thighs because they make headlines.
Yes, we've come a long way, baby.
But Simpson's message about owning her body, ignoring the media, and living an authentic life was refreshingly honest and real, even in its Oprahesque, self-helpy way. Joined by WNBA star Lisa Leslie, self-esteem guru Jess Weiner and Maria Shriver's 19-year-old daughter, Katherine Schwarzenegger, who recently wrote "Rock What You've Got," a book about body image, the women candidly discussed the modern-day dilemma of female self-esteem, unattainable beauty standards, and the relentless pressure of the paparazzi.
While self-esteem is hardly frivolous, perhaps it seemed a frivolity back in the O'Connor-Ginsburg era of gross gender discrimination. Five decades ago, there were weightier issues at stake for women than their personal weight woes. But in a post-Title-VII era, we have the luxury of having lengthy discussions that encourage us to own our curvy hips as well as our brains.
Back in the day, Ms. Ginsburg was more troubled that there were no women's toilets in the Harvard Law School building and that she couldn't get a job interview. Whether the media made her feel fat or not probably seemed inconsequential.
But while we've made incredible progress as women and can collectively get thousands into a room to discuss everything from the need for affordable childcare to weight loss, Justice Ginsburg pointedly shows us that despite the progress, there is still serious work to be done.
"If I could design an affirmative action program, my dream for the world would be for every child to grow up with two loving parents," Justice Ginsburg told the rapt audience. "Women will truly be liberated when men take as much responsibility for raising the next generation as women."
HuffPost Lifestyle is a daily newsletter that will make you happier and healthier — one email at a time. Learn more