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Small Business Heroes

3 Things Every Female Leader Should Know About Being Confident in Her Pursuit of Success

'Weird in a World That's Not: A Career Guide for Misfits, F*ckups, and Failures' author Jennifer Romolini shares her top tips for boldly forging ahead.
3 Things Every Female Leader Should Know About Being Confident in Her Pursuit of Success
Image credit: David Land
Entrepreneur Staff
Staff Writer. Covers leadership, media, technology and culture.
5 min read

The parts of your personality and perspective that may have made you feel out of place are often the factors that will truly help you make an impact.

That’s what Jennifer Romolini says in her book, Weird in a World That's Not: A Career Guide for Misfits, F*ckups, and Failures. She is a career expert who served as the chief content officer of Shonda Rhimes’ and the editor-in-chief of HelloGiggles, a site geared toward millennial women that was co-founded by actress Zooey Deschanel.

But Romolini took a circuitous path on her way to being a boss, starting out in the media industry as a broke 27-year-old divorcee and college dropout. Which goes to show that even if you think that someone has everything together, there is usually more to the story.

It can be so easy to compare yourself to others, but Romolini says that it’s important not to let jealousy stand in your way. Instead, she advises taking a step back and using it as a motivator to find what matters most to you,

“Following our envy to its source is a great tool to teach us about who we are and what we actually want,” says Romolini. “But comparison just for comparison’s sake is a kind of masochism I no longer have time to indulge.”

She says that rather than chasing what a glamorous “influencer” seems like they have, take a hard look at what you want to accomplish, by asking yourself three questions. What work do I like? How can I continue to do it? And how can I get better at it?

And when failures come your way -- and they will -- Romolini says her best advice is, even if it’s painful to unpack what happened, to try and turn that rejection into something productive. It’s okay to mourn what you lost, but don’t let it define you. Instead, channel it into creating something so successful that it is undeniable.

Romolini shared her insights with us about how to find what makes you special and find the drive to unapologetically achieve your biggest goals.

Entrepreneur: What tips do you have for building a support network, especially if you’re just starting something new, whether it’s your own company or beginning in a new industry?

Romolini: Seek out people you admire, whose work you like and respect -- people who are kind, generous and make you feel good about who and where you are. Whenever you can, avoid the charlatans, the movers, shakers and natural-born fakers. Remember a good network is not a quantity game, but a quality one. You don’t need 100 phonies in your network; you need a handful of solid humans with whom you feel aligned professionally, who you can rely on long term, people who ultimately care.

Entrepreneur: How can women avoid the compulsion to apologize for who they are and for their success?

Romolini: I’ve gotten better at this, but I still do it sometimes. I still make myself small when I feel self-conscious, or I don’t want to seem highfalutin, insensitive or disconnected to the person I’m talking to. But what I’ve realized is apologizing or downplaying my success, even if it’s meant to make another person feel better, is actually worse than just owning what I’ve done and what I’ve earned. One trick I use, that I saw in Yao Xiao's great comic once, is not saying “I’m sorry” when I really mean “Thank you.” Now I try to say “Thank you” and move the conversation quickly on to more interesting topics than me.

Entrepreneur: What advice do you have about gaining confidence as a female leader?

Romolini. New leaders tend to enter into management roles in one of two ways. Either “I can be the boss and still be everyone’s friend. I’m the cool boss!” or “I’m insecure about this and afraid I don’t know what I’m doing, so I’ll show my leader competence by unnecessarily asserting authority and power. I’m #bossedup!”

Both of these strategies are flawed. Great leadership is about creating a safe, consistent environment where your staff can freely share their ideas; challenge themselves, each other and you; and thrive. This happens first through genuine curiosity -- by listening to your employees and finding out their ideas and obstacles -- and then synthesizing all of that into a long- and short-term strategy that works for the needs of the company and the individuals within it. Be reliable. Listen more than you talk, ask questions and then sit back and really absorb the answers.

Take your ego out of it. Be humble and kind. Own your mistakes. Set fair, realistic goals. Happy, productive, high-performing employees feel heard, seen and supported. They don’t care if you mess up occasionally, as long as you’re accountable. Demand accountability of yourself and others. Prioritize all of this as your leadership “style,” and you’ll quickly start being great at your job.  Being great, proving yourself to yourself, is what builds confidence as a leader, or really as anything.

Jennifer Romolini recently spoke at Ellevate Network's Mobilizing the Power of Women Summit. You can download the Action Guide from that event here, and learn more about Ellevate Network here.

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