Images courtesy the author, Harper Business

Not to assume too much about you, but Jennifer Romolini definitely has your dream job. She’s the Chief Content Officer of, Shonda Rhimes’ new website that is just about to launch. Shonda Rhimes. Jenn is a boss alongside Shonda flippin Rhimes.

But she wasn’t always at the very tip-top of the career game, making us seethe with jealousy. She wasn’t born rich, she dropped out of college, she pin-balled her way around the world to scrape rent together for many, many years before figuring out what she really wanted to do. And then she took even more time learning how to do it, all the while feeling like she was too awkward or spazzy or simply too much to achieve true success.


Now that she has, she’s letting us all know how you can be both a ding dong and a success in her new book, Weird In a World That’s Not: A Career Guide for Misfits, F*ckups, and Failures. It’s part memoir—and a riveting one, at that—part self-help, in the “you can do it!” sort of way, and partly a practical and straightforward guide to getting where you want to be in your professional life. If you’ve never cared for this sort of book, don’t worry: it’s unlike anything out there. You will not find advice about how to “have it all,” nor will you feel ashamed at not having done it all already. There’s no presupposition that you’ve been to the “right” school or taken the “correct” path thus far. What’s most lovely about this book is that it is for anyone at any stage in life who feels like they just don’t and won’t fit in and “make it.” Jenn proves you can.

Jezebel spoke her about how she got where she is and what steps we need to take to steal her job. This interview has been condensed and edited for clarity.

JEZEBEL: To start this interview, will you just run through your career history as fast as you can?


JENNIFER ROMOLINI: Flower stand outside my dad’s store, video store clerk, telemarketer, worked at Express, worked at The Gap, worked at a pizza place, worked at a Mexican restaurant, worked at a diner, worked at another diner, worked at a Spanish tapas restaurant, worked at a hotel restaurant, worked at a hotel restaurant that revolved, worked at an all you can eat buffet, worked in a French restaurant, worked in a wine bar, worked at a tapas restaurant where I wore a sequined vest and sang “Happy Birthday” in Spanish—got fired, worked at the Beacon Hill paper, worked at the Boston Phoenix, Boston Magazine,, Talk Magazine, Glamour, Cosmo, Poz, Allure, Lucky, Time Out New York, Yahoo, Hello Giggles, worked for Shonda Rhimes.

You mentioned getting fired in there. Whenever I hear people our age talking about getting fired, I’m like, “Uh huh.” And then they’re complaining it’s the first time, I’m thinking what the FUCK have you been doing? You have to get fired or you’re not doing life! I think I’ve been fired three times just for being a human being.

Oh, I’ve been fired for being an asshole. I had a chip on my shoulder for so long and I also didn’t understand that injustice was not your responsibility to point out? And I wasn’t self protective enough. I didn’t realize that if I didn’t tell them the truth in that situation I would be able to pay rent. I was in Express like, “I can’t tell her she looks good in that. I’m not going to lie for six dollars an hour!”


Alright, another list: your weirdnesses that made you think you couldn’t do what you’re doing now.

I drool. I rouge up. Major hives person.

You drool?

I do! In meetings I spittle. If I’m nervous I spittle. I throw limbs. I’m an over-sharer. I have a temper. I’m just a really emotive person with not a lot of ability to hold it back. So I thought, you don’t see people like this in business!


This is echoing a lot of the advice in your book, which is just to be yourself.

Yes! There’s always a side door, as long as you’re ambitious and good at what you do. I think there’s not enough investment in competence and that’s actually so much more important than confidence.

For me growing up, I didn’t know what all was possible in terms of making money. You know those quizzes in 7th grade that they give you where you can only be one of maybe 20 professions and they range from trades to a licensed career like a veterinarian? It felt like I can either be a nurse or teacher. Those are jobs.


I think Sassy Magazine really changed that a lot for me. I remember being like what in the fuck is this? Sassy was the first moment where I was like, wait a second, those are my people! But I never imagined that I actually could do that. Those people have a pedigree, they have connections. But then I finally got to work with those people!

Here’s a question: how do you write a book?

Really? You make a chart. I couldn’t fathom writing a book but then I was like fuck this, I’m gonna write a book. I also have this good-girl thing and didn’t realize deadlines were bullshit. I turned my book in three days early. I approached it like this real good-girl thing, like I have to do this! So I made a chart, a war wall with every chapter of the book and then I had it color coded and every day I wrote 2,000 words. It was a total mindfuck. But I just did it every day because it’s my job. I knew it would be very easy to not do it. It’s cliché writing advice but it actually works.


It’s the advice in The Artist’s Way.

Is it? I own that book but I’ve never read it! It’s like one of those books I just rub on my body.

Why did you decide to make it a choose your own adventure?

You’re the only one who picked up on that fact—that I squeezed a choose your own adventure chapter into the book. It was a huge fight with the publisher because it was a production nightmare, but I felt like as I was writing this book, a lot of this advice has been told before. There are not that many ways to be great in an interview, there aren’t that many ways to build a great resume, but the delivery system could be different and the person giving the advice could be different. I felt like if I told the advice in a different way and was also personal and honest about myself, the advice would get through. Basically I wrote the advice book I wish I’d had.


You and I basically have parallel lives: we had teen parents, we did not get very good grades, and our paths in college were all twisted. I love talking to authors who come from that in order to find out what gave you the nerve to think you could write a book? And that anyone would read it? Does that go through your head?  

Yes! That was the whole thing. I was getting to a point where I was “successful.” There was no denying, no amount of self-loathing. But there was no one around me who was like me. There was no one at that level who was giving advice. Everyone giving career advice was like, “Put on a blazer and wear stilettos and get your hair blown out and don’t have emotion.”

And pretend you went to Harvard...

Exactly, or just never talk about your schooling. And then I was seeing women coming up who were bumbling around in the same ways I’d bumbled around and who were not finding answers. Even though there’s this weird fetish around advice and success porn and leaning in, I didn’t feel like the messages were getting through. So I thought, well, why not try to write it?


How important do you feel like it is to be liked?

Oh god... if you have an extreme personality, which I do, people are going to have extreme reactions to you. So, in every job I’ve been in it’s pretty much half and half. And it’s real love, the people who love me. It’s sincere and I wind up knowing them for years. The people who dislike me, it’s equally strong. And it’s all about learning to navigate that. Because if you’re going to walk this walk of being authentic, then you have no fucking choice about people liking you. I spent a long time trying to make people like me. You know, doing the fake conversations and compliments and pats on the back and it’s just wasted energy. You shouldn’t go out of your way to be an asshole, but if people just don’t like the cut of your jib, what are you gonna do? Also, you can work with people you don’t like. I do it all the time, I mean everybody does. And also the last part of that is that things change. So somebody that you’re like, oh god, I hate that fucking person, after six months or a year or five years, you’re suddenly like oh, I missed that part about them, or I projected that onto them. So fixating on that is actually one of the worst things you can do.

Right, some places you fit in and some places you don’t and there’s not a lot you can do about that. It’s like love.


It’s all like relationships. Matching up to jobs is very much like matching up romantically and there are all these fallacies about it. It really comes down to timing, luck, chemistry, and people wanting you, not just you wanting them.

Jennifer Romolini is the Chief Content Officer at Jane Marie is the host of DTR, Tinder’s official podcast, and owns a podcast production company, Little Everywhere.