Career Advice for Women From a 'Successful' 'Misfit': 'The Two Aren't Mutually Exclusive'

In Jennifer Romolini’s new and unconventional career guide for young women, Weird in a World That’s Not: A Career Guide for Misfits, F*ckups, and Failures, she is merciless in her self-deprecation: She calls herself “awkward” and “a weirdo”; writes “I failed and I failed and I failed,” at college and marriage and finances; admits to having wasted years of her life and having been “unpopular at school”; and that, ever since she was a young child, she’s felt like “an outsider looking in.”

And that’s all before Chapter 2.

Romolini — who, full disclosure, is a former Yahoo editor (and this writer’s former boss lady) — has spent years in the media business, most recently as editor-in-chief of Hello Giggles and, currently, as chief content officer for Shondaland, the new media venture from Shonda Rhimes. The Los Angeles–based editor is also mom to a 7-year-old girl, and is currently promoting her new book, which is part memoir, part advice tome, but definitely unlike anything in either category that you’ve ever read before. Yahoo Style got in on the conversation recently.

So which part of the book was the bigger challenge for you, writing the memoir or the advice part?

I think both things are presumptuous — like, hey! I’m writing a memoir! My life is important! And also, hey! I know what I’m talking about! I’m going to give advice! But I wrote advice that I could have used but didn’t get — and really desperately needed — in all these stages in my career. All the career books I had been reading were not useful to me. I think they forgot about what it’s like to feel low and insecure and gross. So I tried to get specific to the point of being mundane — thinking about people who have worked for me over the years, things that have happened IRL that I could put into a real book. The memoir part was way more vulnerable making because that’s about me, and I felt terribly exposed writing it. But I realized the only way this book was going to be useful was if I said I was trash, I felt like trash, everything was trash. But I kept going, and it worked out anyway.

So I first met you many years ago when we both worked at the same magazine. My perception of you was not as the nervous new person, as you describe in your book, but as somebody who was completely cool, and a bit intimidating. But when I stopped by your desk to chat you were so real and funny and refreshingly down-to-earth. Do you recall what you were thinking?

I remember that time specifically and I can’t believe you thought I was cool. I had two pairs of pants at the time, because I was so broke. I was wearing these purple jeans I had gotten [on discount], they were supposed to be denim colored but something had gone wrong. They were $15.99 and I wore them almost every single day. I remember one of the Style girls asking how I felt about the pants and saying, “I don’t know if they really suit you.” I thought that you were very smart. I thought you were going to find out that I wasn’t very smart and didn’t know how to do my job.

So when did you first embrace your identification of “misfit”? And is there still pain associated with it?

There still is [pain]. I can’t believe how hapless I am every day, how I can’t pull it together to have clothes to wear every day that aren’t dirty. I can’t believe I don’t feel like I live in the world as a high functioning adult and yet am very successful. But what I’ve learned between coming up with the idea of this book and writing it is that the two aren’t mutually exclusive. You can have tons of foibles, and still be successful. As I got further into the book, that was the real takeaway.

I feel like the “Surviving Yourself” section of your book, which deals with rejecting all those unkind, self-sabotaging conversations that women have with themselves, is one of the most important. Why is that such a struggle for young women entering professional life, do you think?

I think that women are still insecure and unkind to themselves, and that, because of the world that we live in now, it’s almost worse. Everything is so image focused and obsessed with sharing really positive images, so people are more afraid to admit their weakness or admit that they’re scared. I think young women are in a really difficult position: They have to be competent younger because a career goes so much faster now. They have to project an image into the world that they have it all together at a much younger age when they might not feel that they do. And they haven’t been mentored well. So it’s not entitlement, it’s just that they’re navigating careers in entirely different ways than we did.

You talk a lot about being a good leader. What if you simply don’t want to be the boss?

I think the meaning of success is that you’re happy with whatever you’re doing, and that you’re doing it as an authentic person in an authentic way. I think that’s it. It doesn’t matter what the job is. It doesn’t have to be the highest rung. That’s a bill of goods we’ve all been sold.

You shared an anecdote in the book about experiencing subtle yet disturbing sexual harassment at work, and about the shame you felt over your reaction to it. Why was that important to include?

I think I wasn’t so much ashamed of the situation as I was ashamed that who I was and who I thought I was wasn’t the same. I really had to deal with the question, “Am I projecting a false sense of feminism?” I took the abuse for quite some time and I was surprised by how scared I was by somebody who was making me feel small and stealing my power on a daily basis. It was barely enough to report to HR, but I knew it was happening, and that I wasn’t crazy. I think the way we overcome that is by having a zero tolerance policy for any inappropriate behavior at work. What I’m heartened to see is that the next generation of women is tolerating this bullsh*t much less than we did.

How are you navigating all of this as the mom of a young daughter?

I mean, I have no answers. I talk to her in the way I wanted to be talked to. I let her know that I’m on her side. I let her know that nothing she’s feeling or thinking is weird. I tell her that she’s smart and she’s sensitive and that people with a lot of feelings sometimes have a harder time in life. I don’t sugarcoat it for her. I just say, “Not everyone is going to be nice, and you’re not going to like everybody, and some people are going to make you feel bad. But that doesn’t mean that you are bad.” That’s the best I can do. She’s 7 and confident to a fault, which is exactly how I want her to be.

In the book you advise women to not fall into the trap being a “flighty-girl cliché” by buying expensive clothing they can’t afford just to look “fancy at work.” Did you do this?

I spend money daily in idiotic ways. But I did see a lot of women who felt pressure to own status items, who felt if only they could dress better — have a new purse, new shoes, these boots — they would have an easier time at work. It’s garbage, and just another way that we pressure ourselves to think that we’re not good enough. It doesn’t matter. I wanted to demystify that.

How do you practice self-care?

I have lots of indulgences that are not so healthy, but I’m pretty strict with my morning routine. I get up before anyone else is awake and I spin or I run three to four times a week — not so much for vanity but for my mental health. I have a shake for breakfast, with a bit of protein powder and vitamins for women and frozen blueberries and almond milk. I sip that while I make lunch and breakfast and sign permission slips and make sure my daughter is wearing two of the same shoes. I stay away from caffeine as much as I can because it makes me jittery and insane. And therapy — my god, who doesn’t need that?

Finally, what makes you feel like you look hot?

A good bangs trim, some red lipstick, and a jumpsuit can get you through anything.

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