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Some of the most successful women in the world may be building business empires, perhaps earning distinguished honors, but, frankly it’s not their title, fancy Fendi bag, or perfect blow out that distinguishes them. They’re the boundary pushers. Game changers. They are the women who drive our motivation and imaginations, merely by their example. If we’re lucky enough, we count them as friends, but more aptly, we call them our mentors.

In kicking off the inaugural edition of R29’s The Mentor Series, we spoke with seven women who are not only leaders in their respective fields, but also fully recognized the power and importance of knowing a woman who challenges and advises them by simply being who she is. Some took on-the-job lessons from Anna Wintour herself, others had Hillary Clinton standing in her (proverbial) corner, and then there are those who never forgot the advice from the wisest lady they know (Hi, mom!). In every success story ahead, the power of a fellow female mentor has proven to be immeasurable, and as we found out, truly inspiring.

Sally Singer

Claim to fame: If you’ve read a Vogue masthead sometime during the majority of the past 14 years (you have, haven’t you?), you probably are already well versed on the massive editorial contributions of Singer. She served as the fashion news director for the glossy before switching gears and moving to the editor-in-chief position at T: The New York Times Style Magazine. In October ’12, Singer returned to Vogue, now overseeing the web version as the creative director of digital.

Tell us about the most influential female mentor in your life.

“I’ve had three female mentors in my professional life who have been incredibly important in the way I shape the way I think. The first is a women by the name of Margaret Simmons of Travel Holiday magazine, which was the first job I got after graduate school. What I learned from her was all the mechanics of relaunching a magazine. The biggest lesson I learned from Maggie, though, was to have incredibly high standards, and to never think you have to compromise your view of what the reader should aspire to think about, read, or look at.

“The second is Sara Bershtel. When I went to work in books, she was an editor at Farrar, Straus, and Giroux (now publisher of Metropolitan Books). She taught me to be a text editor, and to work very collaboratively with authors. I really learned to edit from her. The interesting and important lesson she taught me was that you have to be able to think horizontally. Everything has been published, so what’s the state of your argument? How, then, do you think vertically and dive into the content matter to bring the elements you discovered through horizontal thinking deeper? To be a great editor you have to be able to think in both directions.

“The third is obvious. Anna Wintour. She taught me everything about everything. Anna, I think, has taught me to always be true to myself; to fight for what I see. She’s always been interested to see how I see things, but has taught me to take my idiosyncratic points of view and convey them to a very large audience. In other words, she taught me how to go from indie movies to Hollywood blockbusters in the way I see fashion and features, without ever compromising who I am in the process. It’s a really hard thing to learn, and she does it effortlessly.”

What’s the #1 piece of advice that has always steered you in the right direction?

“When I was thinking about leaving T, Anna suggested I take the job I have now as creative digital director. She said it’s a job I should have now based on the fact that I’ve shown I can do it and because it’s a job that will define the industry going forward. I felt that was an incredibly generous act; what she was saying was that she was thinking ahead for my interests. She knows print journalism, but she was thinking in the arch of my career what’s the next stage I needed.

“The trick to being a good mentor is not just answering someone’s immediate question, and not reassuring people that it’s fine; it’s about thinking about who is the person before you and what do they need that they might not even know they needed? To be a good mentor you have to really understand the person who’s looking to you as an extension of who they want to be, and how can you help them.”

How do you think YOU’VE been a good mentee?

“Well, I listen. I don’t look to people to confirm basic levels of self-worth. I sort of know who I am, and I know the things Anna amused me with. I believe that the point of going to work in the fields we work in is to be fun. You should really like the people you work with, and you should enjoy the privilege of doing it. I’m really loyal to the people I’ve worked for and worked with in my life. I take great pride and great pleasure that I’ve been able to work with them.”

Why, more so than ever, do women need a strong mentor? What do we gain by having one? And what do we risk without their guidance, wisdom, and example?

“Over the course of a career and decades of your life, so much happens: children grow, health concerns change, all of these rite-of-passage moments happen just as women move up in the work force. You can keep all of it out of the office, but it is important that other women know that. They don’t have to talk about it, but they have to get it. They get it when your children are sick. They get it when your relationship is good or it’s bad. There are specific pressures and rites of passage women go through. It’s invaluable to know someone understands.”

How do you think the Internet and social media have changed the way women find a mentor? Does mentoring work just as well over the web?

“I imagine it can. I know, anecdotally, women who have formed relationships (email or text) with someone older over the web — in fashion particularly. Tavi first met the girls of Rodarte because of something she blogged about. There’s a very young generation, and not just women — my son, who’s 14 now, when he had a question about skate shoes, he’d email a terrifically skilled skater to get an answer. You can access people if they’re game for that kind of relationship.

“I think there’s a value in daily contact. There’s a value in watching someone over time, but that could be because as a journalist and when I interview, it’s never what I ask them; it’s how they move within a space that fascinates me. For a relationship that’s lush and complex, and rewarding over time, it might start online, but I’d hope it would evolve to something where the computer gets turned off.”

Judith Jamison

Claim to fame: Jamison is currently the Artistic Director Emerita of Alvin Ailey American Dance Theater, but the reputation of her historic dance career precedes her. The dancer, choreographer, and creator of her own company, The Jamison Project, is recognized world wide for her contribution to the arts and the many awards she’s earned, including an Emmy, a Kennedy Center Honor, and a place in the Hall of Fame at the National Museum of Dance.

Tell us about the most influential female mentor in your life.

“There are too many to name! It’s not just one female who did anything. My opinion is that no one female does anything for one female. We do things without even knowing we’re touching other people. I’ve been very fortunate to have many women help me. I have to start with family first because you have to start with your mom. My mom would always say — she loved Shakespeare — ‘This above all: to thine own self to be true.’ It just sticks, and it’s worked all my life.

“There’s my ballet teacher, Marion Cuyjet. She was my first at the age of six. In my home, you learned the importance of sharing and being kind to others. This was reinforced by Cuyjet.

“Carmen De Lavallade. When I first came to New York, she and her husband Geoffrey Holder, embraced me. I had seen Carmen on television in the ’50s. She was the first woman of color I had seen dance on television, and doing something other than ballet. She certainly was an inspiration to me — just by her presence. She didn’t have to say anything even though she was remarkable with words. She reinforced me to keep my feet grounded and let my head stay in the clouds. She taught me that fame and beauty are fleeting, but what’s interior is important. You have to be there as a performer to not just show up, but to stay connected.”

Why, more so than ever, do women need a strong mentor? What do we gain by having one? And what do we risk without their guidance, wisdom, and example?

“It’s someone to emulate and then go beyond. If you have it in front of you — dancers are famous for this because we emulate all the time — the honest example bolsters you. Dancers go through their moments of, ‘Oh, her leg is higher than mine.’ That, to me, is exactly the competition you aspire to, but you have to be competing with yourself. You are always raising the bar for yourself, and in dance, there are other dancers to watch.”

How do you think this translates outside the dance world?

“You become responsible with what you do on stage. Of course, if you’re fabulous, make it your whole life; aspire to that kind of level of excellence. It all translates the same. Life, love, dance, move, etc. You’re always on.”

How do you think the Internet and social media have changed the way women find a mentor? Does mentoring work just as well over the web?

“I’ve done it before — not very well — but I have done it. There are so many levels of it on the web. It’s the difference of having a book in your hand and having a Kindle (I happen to love both). I think whatever can reinforce the mentorship of being there in actuality is excellent. I just fear the erasure of the one-on-one. Since we’re proliferated with 21st Century technology, then God forbid we don’t use it to its fullest and connect to as many as people, especially young women. They have to know someone cares.”

Whitney Cummings

Claim to fame: You probably have Cummings to thank for many a laughing fit, and probably several hours of productivity lost to YouTubing some of her best stand-up acts. The actress and comedian is a regular guest on The Chelsea Handler Show, and is the creator of 2 Broke Girls and (sadly, now-cancelled) Whitney.

Tell us about the most influential female mentor in your life.

“I think Chelsea Handler was a mentor to me early on. She’s like the worst possible mentor to have, being the drunken fool that she is, but I think she mentored me without knowing it because she was doing a lot of the things I saw myself doing and doing them with such fearless qualm. She was kind of the first female comedian I was able to look to. I didn’t have to make myself masculine or ambiguous – she was really the same person on stage and in her show as she was offstage as a person. That was the first time I was like ‘oh, you don’t have to be different, you can be authentic.’ It seems really obvious but I think that’s something that takes comics a long time to figure out.”

What makes a mentor truly amazing?

“I think the best thing about a good mentor is that they’re not someone who tells you what to do, they let you have your own experience and are a good role model. You can look at them and the choices they make and that inspires you to make choices unique to you. A mentor shouldn’t just be someone you emulate, because then you’d be a carbon copy and that’s not original. It’s someone who inspires you to be the best version of yourself.”

Tell us about a time you needed your mentor the most and she really pulled through for you.

“I was trying to figure out how to do a talk show and she was straight with me and told me things no one else had the balls to tell me. She was like ‘why are you talking so loud? It’s annoying.’ It was a really good point that no one else would have told me. And then she was like, ‘Why are you wearing high-heeled shoes? You never wear high-heeled shoes in real life. Just wear sneakers.’ I thought if I’m on TV I need to wear high heels, it was just really obvious stuff that I missed.”

Why, more so than ever, do women need a strong mentor? What do we gain by having one? And what do we risk without their guidance, wisdom, and example?

“Well, because we need emotional support. That seems like a question that is so obvious [but] it seems hard. We need love and encouragement and emotional support and to not be competitive with each other, because otherwise you’re just alone. But, women can provide that kind of emotional support. I think families are getting more and more dysfunctional now, and we choose our families. And, if your mom didn’t do it right, or your dad didn’t do it right and provide you with the guidance you needed, you can choose your own family later on in life in the form of mentors and friends.”

Kate Somerville

Claim to fame: Kate Somerville’s name is likely one that’s splashed all over your medicine cabinet. The estheti­cian is the founder of Kate Somerville Skin Health Experts and, as such, has developed her own skincare line and methods for improving the health and appearance of women’s and men’s skin across the globe.

Tell us about the most influential female mentor in your life.

“Barbara Wells: She was my college boyfriend’s mother and remains the most inspirational woman I have ever known. She was loving and supportive and taught me that I didn’t have to live in chaos. I was in control of my life, and I had the power to change whatever it was I didn’t like. I could be whatever I wanted to be, have whatever I wanted to have, and achieve whatever I wanted to achieve. Even today, I continue to play her words of encouragement in my head. Barbara was my guiding light, showing me that anything is possible in life. After having battled cancer for 10 years, she died from the disease when I was about 20. Her message continues to guide me, personally and professionally.”

What makes a mentor truly amazing? And in turn, how have YOU been a better mentee to that person?

“What makes a mentor amazing is support, guidance, and life experience. Self-reflection is a huge part of this process. As I meet challenges in my life, I take the time to think about the tools I need to succeed, and I look back on what was successful in getting me through difficult times. It’s not only about challenges, it’s also about celebrating the small victories! One of our biggest tools is our ability to stay positive — give yourself the benefit of the doubt, and get out of your own way!”

What’s the #1 piece of advice that has always steered you in the right direction?

“I would go on and on to Barbara about my troubles and my disappointments. One time she told me, ‘You know, you have a choice. You can make your life good or you can continue to dwell on your hardships.’ I honestly didn’t know that I had a choice, but because of Barbara, I was finally able to make decisions based on what I wanted.”

Why, more so than ever, do women need a strong mentor? What do we gain by having one? And what do we risk without their guidance, wisdom, and example?

“Experience is such an important factor in being a mentor. When you speak to someone with 20 years of experience, you are learning from the years of their successes and failures. You’re learning tips and tricks and wisdom from someone who has seen a lot and been through a lot. There’s beauty in that experience and wisdom. You can learn valuable lessons, but you must be willing to listen and apply those learnings to your own life.

“As a mentor, listening is really important, too. It’s not a one-way street. The more I know about someone I am giving advice to, the better I can assist them in achieving their goals. Women are expected to do it all, and do it well, and it’s important to know that, as women, we have a community. We have a support system to guide us and empower us to be the best versions of ourselves.”

Reshma Saujani

Claim to fame: Saujani is the founder of Girls Who Code, an organization aimed toward providing young women with the resources and education to pursue careers in technology. In addition, she also has held the position of Deputy Public Advocate for the City of New York, and recently ran for Public Advocate. Saujani’s book, Women Who Don’t Wait in Line releases October 8.

Tell us about the most influential female mentor in your life.

“Hillary Clinton has been the most influential mentor in my life. I met her while volunteering on her campaign as a fundraiser when I was a young lawyer, obsessed with politics but still on the sidelines. There was this culture of encouragement and sponsorship that started at the top with Hillary. She would always look for opportunities to let me introduce her, or call to say thank you and congratulations after an event. Years later, I feel — and I think many women in politics feel — a sense that she has our backs.”

What makes a mentor truly amazing? And in turn, how have YOU been a better mentee to that person?

“An amazing mentor is someone who guides you both with their words and deeds. We may not have the same goals, but good mentors help their mentees along their own paths. Being a good mentee sometimes means dropping your guard and letting your mentor support you, especially when you encounter obstacles along the way. Women sometimes are so ashamed of our failures that we don’t talk about them, and we have to!”

What’s the #1 piece of advice that has always steered you in the right direction?

“During Hillary’s concession speech in 2008, she said something to the effect of, ‘Just because I failed, doesn’t mean you shouldn’t try, too.’ That stuck with me, and it’s something I shared with my own campaign volunteers on election night after I lost. As women, we have to keep running, keep applying for the job we don’t think we’re qualified for, keep reaching. That’s how we win.”

How do you think the Internet and social media have changed the way women find a mentor? Does mentoring work just as well over the web?

“The web has changed mentorship vastly, both vertically and horizontally. There’s nothing to stop a young woman in tech from tweeting at a celebrity or a CEO for advice. At the same time I’ve seen girls from my Girls Who Code program in Detroit connecting with girls in our California and New York programs for peer mentorship. The boundaries of the sisterhood are being eliminated thanks to social media.”

Why, more so than ever, do women need a strong mentor? What do we gain by having one? And what do we risk without their guidance, wisdom, and example?

“I love the quote ‘you can’t be what you can’t see.’ Sponsorship and mentorship is what feminism today is all about, and especially in career fields where there aren’t a lot of senior women. Role models are essential for closing the gender gap. There are so many factors that discourage and derail young women — from a stereotype that girls aren’t as good at math and science to a T-shirt at Forever 21 that says ‘Math Sucks.’ But, the reality is women like Sheryl Sandberg, or a female computer science teacher in your high school, or a rock star engineer at a tech company can trump those notions in a powerful way.”

Jennifer Baumgardner

Claim to fame: Baumgardner is a journalist whose profound work can not only be found in publications such as The New York Times, Harper’s Bazaar, and Glamour, but also within the six books she has penned. An activist, filmmaker, and inspiring voice of female empowerment, Baumgardner currently holds the position of executive director and publisher of Feminist Press.

Tell us about the most influential female mentor in your life.

“I’ve had many, but the one who really stands out is Barbara Seaman, who died in 2008. She was a magazine writer, author, and a founder of the women’s health movement — but also an amazing character. She knew and connected everyone. I met her when I was a lowly editorial assistant at Ms. Magazine. She called, invited me to lunch, and then asked if I would introduce her at her book party the next week that was being hosted by Shelby and Cy Coleman (the Broadway composer). Oh, the other person, besides me (a no name 22 year old from Fargo) who would be making remarks was Katie Couric….she would just sort of drop that kind of fabulousness in and act like it was normal. She would always say things like ‘When you win a MacArthur Genius grant…’ or ‘You really remind me of Gloria Steinem’— she saw things in me I wanted to be and then I tried to be them to meet her expectations.

“What made Barbara so valuable is that she supported me like a grandmother (knitted my son a hat, gave me cab money), but she was also a very radical feminist who knew everyone in the Women’s Liberation Movement— from Andrea Dworkin to Flo Kennedy to Kate Millett and on and on. I could call her at midnight if I needed to and she would pick up. I think I learned from her the concept of co-mentoring or mentoring down, as she really made me feel that she was learning as much from me as I was from her.”

Tell us about a time you needed your mentor the most and she really pulled through for you.

“I was going to Cosmo to interview Helen Gurley Brown (and I was quite fascinated and intimidated by HGB). Helen had been interviewed thousands of times — what could I possibly ask that hadn’t been asked a million times before and would prompt new insight? Barbara had randomly met a retired Brooklyn College professor named Suki Nishi the week before who had mentioned she went to high school, in the 1940s, with Helen Gurley. Barbara suggested I call her, saying, ‘it’s these unexpected interviews that give biographies and profiles life.’

“So, I interviewed Professor Nishi and learned that during the height of anti-Japanese sentiment in the U.S., Helen had lobbied for Suki to become the first non-white member of some honors club at their high school. Soon after, Suki and her entire family were sent to an internment camp in the US. Helen was the only friend from high school that wrote to her during that ordeal. I loved learning this, because conventional wisdom had it that Helen was a grab-a-martini and get-a-man kind of pre-feminist, but I think her instincts were always very humane and ahead of her time — when it came to race, women and human rights. I was able to get her to talk about Suki and how she had the strength to do the right thing even at that young age.

“The interview was a peak experience for me. A few days later, I received a typed note on Helen’s personal stationery. She told me that after 40 years of being interviewed, no one had ever talked to her about that time or Suki and that provoked memories long since dormant. Barbara was so right about getting those off-the-beaten path interviews and that success changed my approach to writing stories.”

What’s the #1 piece of advice that has always steered you in the right direction?

“Pick up the phone. By which, I mean, make the personal gesture, verify, and take initiative. Like many people, I send emails with requests I’m too scared to make in person. Heartfelt, direct, sensitive personal requests are persuasive. Everything else is just more spam.”

Caroline Ghosn

Claim to fame: Ghosn is the founder and CEO of Levo League, a start-up social network aimed toward providing career advice, mentor connections, and helping the women of Gen Y break into and excel in their careers.

Tell us about the most influential female mentor in your life.

“I have multiple female mentors who have had transformative impacts on my life, to the point where narrowing it down to one person would be unfair to the others who have put their time, secrets, and in some cases, political capital on the line to help me succeed. The group of advisors and investors that I work with through Levo — whether it be Fran Hauser, Kelly Hoey, Gina Bianchini, Susan Lyne, Lubna Olayan, or Sheryl Sandberg — are leaders who mentor me through the journey of setting Levo up for success and setting myself up for professional success and happiness on a personal level, because I believe that those two are aligned around the same mission.

“I met all of them through the uncomfortable process of gathering feedback for and pitching our startup in its infancy, and they serve as a reminder of what incredible things can come from pushing your personal limits, meeting new people, and daring to ask them for their support. This is something that I have only recently learned to do, and that I 100% advocate young women become more comfortable with: Overcome your fear of asking. If I had followed my fear, I never would have asked Sheryl to invest in us, especially since she hadn’t invested in any startups before. The moral of the story is: You get what you ask for.

“Beyond Levo, I have had a mentor, couture designer Reem Acra, outside of my sphere of day-to-day operation, which has been an incredible blessing and source of perspective. She encouraged me and assured me that I had ‘something special’ before I had taken any of the leaps that I wanted to in my career. ”

What makes a mentor truly amazing? And in turn, how have YOU been a better mentee to that person?

“I believe what defines an excellent mentor is their ability to give you feedback that isn’t always aligned with their own experience or interest, because this proves that they are empathizing with you and your path, independently of how it reflects on or affects their own. This is, coincidentally, one of the toughest things to do, which I have also learned from being a mentor myself.

“On the mentee side, let’s not forget that we are all human and all need affirmation. That executive who you idolize? She might not know that she has a reputation amongst young startup founders for being a joy to work with. She may never receive candid feedback in her workplace, because as the boss, people will be unlikely to confront her with her own opportunities for development. You can provide that as the mentee — you have license, as well as (in my humble opinion) an obligation, to help her be a more aware and better person out of this two-way street.”

How do you think the Internet and social media have changed the way women find a mentor? Does mentoring work just as well over the web?

“Technology like Levo’s Connections hub has allowed us to democratize success and mentorship, to make it available to everyone. For every one mentor there are hundreds, thousands of mentees — all hungry for advice and guidance. Technology lets us make the most of those conversations that have been typically reserved for one-on-one settings in the past, providing an open forum for all to benefit.

“The web presents an extremely powerful mentorship access opportunity. Our Office Hourssessions have the ability to serve millions of people around the world, which is something one-on-one conversations cannot do. When we sat down with Warren Buffett to share his mentorship advice, he transformed the lives of nearly eight million people instantly, the equivalent of having continuously mentored Gen Y-ers in 78 global locations for four years. Technology is the key to that kind of scale and that kind of democratic impact.”

Original post by Gina Marinelli on Refinery29