Did you excel academically your whole life, only to feel like the world shift beneath your feet once you entered adulthood? There’s a reason for that: the ways women excel in school isn't what's valued in the working world. Claire Shipman and Katty Kay unpack this phenomenon in their new book, The Confidence Code for Girls. Shipman joined me on The Ladies Room to talk about how women are set up to fail.

Shipman thinks we're teaching girls the wrong lessons, focusing on "coloring in the lines, sitting quietly for the teacher, pleasing people," and putting emphasis on gets As. As a result, girls internalize those skills as what they need to do to succeed. But it's a bait-and-switch situation, Shipman says, and the working world celebrate an entirely different set of skills.

What young women need to survive is confidence, not competence. It's a big problem that parents encourage young women to be people-pleasers. “It’s so much easier as a parent to have a people-pleasing girl who is focused on outward success," Shipman says. "Who doesn’t want that? You have to actively fight against that and to keep reminding yourself that gliding through life without experiencing failure is not what you want for your child.”

Not surprisingly, boys are more confident because they’ve been taking risks and failing their whole lives. They weren’t over-preparing. As Steven Colbert admits, men don’t over prepare. Instead, “we wing it!”

Why aren’t women confident enough to wing it? “It’s that feeling that we’re not quite good enough, we’re not confident enough to wing it. We’re not quite the experts we’re making ourselves out to be, so we better just know everything," Shipman says. "I think the most important thing again for women to understand about overpreparing in life is a zero-sum game. We have a finite amount of time, so you don’t want to spend a lot of time on stuff you don’t need to be spending time on.”

So what does it take to be more confident? “The testosterone [boys] are getting at puberty makes them more able to take risks, and risk is an important and essential component for building confidence," says Shipman. "To build more confidence you need to take risks, fail, struggle, work through it. That builds confidence.”

Not only is it okay to fail, it might be the the best thing for your career in the long run.

Make sure to check out The Confidence Code and The Confidence Code for Girls. For more conversations from The Ladies Room, be sure to follow Refinery29’s Strong Opinions Loosely Held page.