When it comes to examining women and self-confidence, there is probably no one on the planet more qualified than Jess Weiner. A pioneering leader in the area of self-esteem, Jess travels the world speaking about self-image and self-confidence. She has consulted as a brand strategist for such giants as Wal-Mart, Time Warner Cable, Yale, Harvard, and the Centers for Disease Control, and serves as Global Ambassador for the Dove Movement for Self-Esteem. Her work has been featured on major media outlets including the Oprah show, the Washington Post and New York Times. She writes for MSN.com and Seventeen magazine, is a frequent contributor for "The Today Show" and CNN's "Showbiz Tonight," and in January 2010 was named by Forbes.com as one of the "14 Power Women to Follow on Twitter." We recently spent a delightful hour with Jess talking about what it takes to be an entrepreneur and about women and self-confidence in business. — J.D.M.

How did you become a spokesperson for women's self-confidence?

My story is similar to many entrepreneurs' stories: I started by following my passion, which at first was performing. I went to performing arts high schools and middle schools and thought I wanted to be a writer/actor.

That passion collided with some personal issues, including my own lack of self-confidence and feeling depressed about my appearance. I had a lot of teenage angst, and this propelled me to pursue another passion, which was connecting with people and talking about issues that could sometimes be hard to discuss.

In part, this was a direction I took for self-healing. Combining that with my passion for the performing arts, I also found a way to make it into a career by creating a nonprofit theater company.

How did you do that? It's not like there's a job application you go fill out!

When I graduated from college, I had three Bachelors degrees: in classics, in theater arts, and in women's studies. That basically qualified me to think, talk, and be an activist—but I had no idea how I'd get paid for doing those things!

So I set out doing a more traditional path, going to work in children's theater, thinking maybe this would be the way to express myself.

I soon found that was not the case. Most children's theater was about fairy tales and fantasy, not reality and social issues.

So I took a grant-writing class at a community college. Part of our finals project was to fill out a real grant application, and I did mine on the idea of starting a nonprofit theater company. I was awarded $5,000 from the Eli Lilly Foundation, and from that money, I started my business.

I started going to theater companies and asking if they wanted an educational outreach arm. I said, "I'll create it, all I need you to do is pay for the rent. Can I have this basement office?" They said yes.

I cobbled together my board of directors and used a local university as an outreach arm to get students involved.

How did you know what to do?

I started with what I had seen at college when I'd started a student-run theater company there, and replicated that out in the world with the little bit of seed money from my grant.

And then I started asking questions.

If you are in business for yourself, you cannot be afraid to ask silly questions. I was twenty-one years old; I had no idea how to make a budget or ask for matching funds. I didn't know how to build a business. So I asked people.

My naiveté really helped me. I would think, "I might as well call so-and-so and ask them for $10,000. Why not? I have nothing to lose." Not everything I did was a 100 percent hit. But I had more hits than the average bear would, just because I asked.

Within six years I had built a company with sixteen people on staff and an operating budget of $300,000. We had almost sixty actors working for us full-time, doing shows in prisons, hospitals, and school systems.

That's amazing! How did you achieve such rapid success in that business?

Not being afraid to ask "silly" questions (which often turned out to be great questions) was critical—and so was having the commitment to take action. I'm very diligent whenever somebody gives me a lead.

When somebody said, "Call my friend Fred, he's an entertainment attorney and he can help you with something," I didn't sit on that lead—I called Fred. And maybe Fred wasn't the guy I needed to connect with, but he might lead me to someone else.

I still do that today. I look at it as a big game of life, and that's how I think you have to play it.

Follow the bread crumbs in the forest.

That's really it. I think what comes up for a lot of people is the fear that they're going to fail. Or procrastination, or laziness, which are often rooted in self-sabotage.

What was the core message you were communicating in the presentations your nonprofit was doing?

My intention was to work with ripped-from-the-headlines stories about youth issues, which meant drug and alcohol abuse, homophobia, hate crimes, self-esteem and body image, all those things that were affecting people my own age at the time. I wanted to translate the news into something creative—a play, musical, or dance number, whatever would evoke people's feelings around it—and then talk to them about taking action.

It was very service-driven, very health- and healing-driven.

This is going back almost eighteen years now, and our media was very different then on these issues. They were often stigmatized in the media.

And simply less talked about.

That's right. It's been a blessing to get the kind of coverage I have in my work. I still remember the early pieces in the Washington Post and New York Times—they were groundbreaking.

Today you see these things covered every day on someone's blog. Especially with social media, our communication has really evolved. But when I was first speaking out on issues like self-esteem and body image, there weren't many people doing this.

And on issues like bullying in schools, we weren't hearing anything at all.

No, and I think those issues have actually been exacerbated by social media. That's why I think we hear about them more from the same sources that are making them worse.

The connectivity is different today than when I started. When we were doing our presentations in those early years, we would actually get in the car and drive out to those schools, hospitals, and prisons. We had no Skype, no DVDs. We brought live art to people and places that didn't have that kind of exposure.

I don't know if a company like that could exist as successfully in today's market.

How has your approach shifted in the years since?

A pivotal moment came in 1999 when the Columbine massacre happened.

I had written a play entitled Battered Souls that centered on the life of a school shooter. We were hired to put on the play at the schools surrounding Columbine that were affected by the shootings. It was so powerful—and it also showed me that the nature of connectivity to our audience was changing.

Reality shows were starting to populate television, and more and more kids were getting personal cell phones and their own email accounts and getting online.

I wanted to match my audience and go deeper into the media.

Given that I had no background in media, I went back to my mentors and business contacts and asked more questions.

"How do I get more involved in the media? How do I make messages that eight billion people see, versus the eight hundred kids in an auditorium?"

The next year I moved to Los Angeles to crawl into the belly of the beast.

And that changed your whole approach?

That has been the most significant change. My focus shifted from direct, face-to-face interaction with an audience to reaching them by influencing the media they consumed.

This changed the scope of my business, too, because I started working more in the capacity of a spokesperson and consultant wielding influence from the inside.

At what point did you start working with large companies in their media campaigns?

This was another huge shift.

When I changed my focus to media consulting, at first it was still all about working with nonprofits. Then Dove approached me five years ago. Their Real Beauty campaign was revolutionizing the way we talk about true beauty versus the airbrushing/retouching kind of beauty we typically see in ads and the media. They were looking for a spokesperson to communicate to the daughters of the moms who were their primary audience.

That whole campaign was so common-sense that it was completely outside the box.

You're exactly right. It was almost as if Dove had pulled out of our heads what we were all thinking and put it out there. Women were saying, "Oh, my God, that's exactly how I feel! That's what I want to see!"

Because Dove did that, today this is a commonplace conversation.

It was exciting to join them and feel that I could help make sure the messaging they were delivering was sound, sufficient, and authentic.

This has also helped me understand the role corporations can play in social responsibility through PR and marketing. Now I'm really enjoying the chance to consult to corporations and work with brands.

Maybe its my radical New England roots showing, but we're so used to vilifying large corporations that the idea of their being a positive force in terms of self-esteem is incredibly refreshing.

I'll tell you, I join in your skepticism, and I haven't drunk all the Kool-Aid. But my vision for my business is to have a far-reaching impact on the way people, and women and girls in particular, think about their confidence and self-esteem. And one of the biggest influences in this, like it or not, is media and corporate advertising.

You can either stand on the outside and protest and critique it, which we need people to do, or you can work on things from the inside, which we also need.

Sometimes people question working with a business that may have a controversial parent company or an unfavorable ad campaign for a different product. And those are valid critiques. I just don't want us to throw the baby out with the bathwater. I look at the impact I'm seeing firsthand. Like the girl who walked out of a London workshop, feeling like a million dollars because she had been able to say something to her mom that she normally could not have said, because of the curriculum this company provided. Those, to me, are really valuable moments, and I attribute that to the corporation's willingness to take that risk.

And to your being open to the opportunity in the first place.

Well it was certainly unexpected! I don't think this could have worked out nearly as well if I had tried to plan it. I've learned to have a dream, but not hold on to it so tightly that I don't let it have its own life.

I think our dreams and goals give us a vision, but we can't get attached to their coming out exactly as we imagine, because that could be limiting. Some of my dreams have turned out way bigger than I imagined. Some haven't happened at all.

I've learned to say, "Well, that one didn't work out, but this one did, and who knows where it's going to lead?"

The way I describe it is this: "When you're following your dream, don't listen to what anyone tells you—and at the same time listen to what everyone tells you."

Exactly! I think that's great advice, because you actually will get to what your gut is telling you.

Your gut is your internal GPS. My gut has never led me astray. What's led me astray is my mind, my ego, my ambition. But when I say, "Is this a person I want to do business with, yes or no?" my gut has always been strong. It's when I try to rationalize it that I get into trouble.

Do you see certain challenges and certain strengths that are particular to women in business?

Yes, to both.

Women still don't earn as much as men do, at least in traditional business. Right now we still earn on average 79¢ for every $1 a man earns. I wish that were an outdated statistic, but we haven't moved the needle much, and that still sends the message that we are almost worthy, but not quite.

On the other hand, a lot of women are entering the workforce and creating their own businesses, and I think that's fantastic.

I'm seeing women holding a lot of positions at very high corporate levels. In fact, they are largely the people steering that shift towards corporate social responsibility, towards authentic and empowering messaging.

I think women often get a bad rap for being overly emotional in work, but I have to tell you, I think that kind of connection to feeling and connection to humanity is what we need more of in our work.

I also think today's woman is very distracted by cultural messages about weight and appearance. If you don't feel you match society's definition of beauty, it can wreak havoc, especially for women over the age of forty. In the media women over forty disappear. You just don't see them anymore. In television commercials, it's like you go from being twenty to being eighty—there's practically no in-between.

A forty-five-year-old woman is seeing her body begin to age and progress in a different way, which is completely normal—but we live in a culture that constantly tells us we can never be too young.

I think this plays upon questions of confidence women often have: "Am I still sexy? Am I still important? Am I still vital and relevant?"

How that plays out in business is they may not take the risks required to grow their business because they feel bad about their appearance—even though the one has rationally nothing to do with the other.

Let's say I am a woman in my fifties. I've never built a business before. What can I do to build my genuine confidence?

Especially for women of that age, I love focusing on the business of being you. Take an honest assessment of your business acumen and skills that you might not even think of as business abilities.

For instance, are you that person who can talk to anybody in line at the grocery store or post office? That ability to smile at someone and make an authentic connection, to take small talk into something deeper—that's an incredible business skill.

It's also important to look at your relationship to saying no and saying yes. This is huge, especially for women in business. Women do not like to say no. We feel we're going to let somebody down. We have this people-pleasing gene. I know I'm giving sweeping stereotypes here, but in general it is harder for women to negotiate, to say no to what they don't want, and to say yes to what they do want and believe they're worthy of receiving it.

You may have dealt with setting boundaries and saying no while raising children—well, it's a critically important skill in business, too!

Even something as simple as saying, "I have ten minutes for this phone call," and then, when the ten minutes is up, saying, "Okay, I have to stop now."

Yes! I'm bad at that. That's something I am absolutely working on. If I added it all up, I have probably spent hours, maybe even days on the phone with people who were not helping me build my business or reciprocally giving anything back. I'm learning to say, "You know what? I'm sorry, that's all the time I have," or, "Let's just do this on email—it's not necessary to get on the phone."

If a guy says, "My ten minutes are up and I really have to go," he's just being firm. But if a woman says it, the perception often goes, she's being something else. Is that an issue there?

Yes, she's being the b-word! That's the thought we default to when women exert their power. But having firm boundaries and a clear sense of your ambition does not make you masculine—and it does not make you a bitch. It makes you a good business person: someone who is mindful of her and others' time, of the bottom line, of finding the right partners to serve the goal she is going for.

You can always make more money, but you can't get time back.

Those are the building blocks of a great business: using your own strengths and skills, becoming comfortable with creating boundaries, and managing your time well.

It boils down to who are you being in your business. For me, that is what makes a strong business and a strong business leader.

When you value yourself, your time, your ability to make money, and what you can offer others, then you don't have to push, or oversell, or be too aggressive, because you're starting from a place of confident respect.

From a practical standpoint, I liken self-confidence to fuel for your car. You can't fill up your tank once and expect to drive your car the rest of your life. You have to constantly refill it, every day. Same thing with self-confidence.

You have to build your life so that you are feeling the most confident you can, and even on days when you lose a connection, or someone who's working with you quits, or whatever the setback is, you can separate yourself from that obstacle and not lose yourself in what's happening. That's a powerful life lesson.

And that's really it, in the end: it's life. Your business is a reflection of your life.