We sat down with Jenn Romolini, author of the new career guide and book, Weird in a World That’s Not: A Career Guide for Misfits, F*ckups, and Failures, and former Editor-in-Chief and VP of Content of HelloGiggles, to chat about embracing your awkwardness and vulnerability in the workplace, how to say no to people, and what it was like meeting Shonda Rhimes for the first time.

Can you tell me about where you grew up and how you think your childhood influenced your ideas and creativity?

Well, I was the child of teenagers—my parents were 16 and 17 when they had me. They weren’t conservative, they were kind of wild teenagers. I was the only kid around, so I was lonely a lot and I was in a lot of situations with adults. I was going to grown-up parties, sharing space in our van, sharing one motel room. So it was kind of bohemian in some ways and I felt like I was very inside myself, looking out all the time.

And then the second part was that we didn’t have a lot of money and my parents were high school dropouts. My dad worked in the stockroom of a grocery store, and my mom was a stay-at-home wife. Eventually, they built a small business together and I watched them work really, really hard. I think that influenced me and my work ethic. In our family, you couldn’t be lazy and I came away learning that that you could get far by working really hard. I learned the value of hard work that way.

How did you become a writer? Is this something you knew you’d always want to do?

This is something I’m trying to debunk in this book. These origin stories that are fanciful. Like, “A magic sunbeam shone on my face and I just knew!” It’s like…maybe there is something about me that wanted to be a writer, but I wasn’t admitting it to myself for a long time. It felt very highfalutin and far from my reality. And when I did finally entertain it, I found it very terrifying. I felt writing to be very self-esteem-eroding and I was afraid to do it and I couldn’t fathom it. Eventually, through trial and error, I found that it was the thing that I’m most interested in.

I think we romanticize our careers and origin stories in the same way we romanticize love, and I think we have to stop having that kind of language around our lives and professional lives. It makes you think that if you don’t know it, you can’t do it. It’s important to actually stumble around a lot.

I think we romanticize our careers and origin stories in the same way we romanticize love, and I think we have to stop having that kind of language around our lives and professional lives.

Do you feel like you got to where you are today out of luck, or through hard work?

I think it’s a combination. I was a pretty earnest and sincere person, and I think there was a lot of goodwill around me. I think more than luck that was it. People cared about me and wanted to help me. But certainly, I muscled my way through the last twenty years—it’s never easy! With this most recent job I took on, I got it after Shonda Rhimes emailed me about it, and I guess in a way that was easy. But that doesn’t mean the work itself is going to be easy, nor am I not going to have to prove myself every day.

I guess once you’ve established yourself in your career, as you have, opportunities like that may be easier to come by.

Does it come easy? I don’t know, when I saw the Shondaland sign, I still had to tell myself like, “DON’T TAKE A SELFIE.”

Let’s talk about your book, “Weird in a World That’s Not: A Career Guide for Misfits, F*ckups, and Failures.” What made you decide to write it?

Well, there were two things: first, it was for me, and second, it was for the people I was managing and the women I was meeting.


I reached a point in my career where I was an Editor-in-Chief and Vice President, so objectively I had “made it.” But I didn’t really FEEL like the models of success I was seeing. I didn’t feel poised, I didn’t feel like I was #havingitall. None of the pictures of slick, Wonder Woman posing, perfectly coiffed woman felt like me. I felt really anxious still, and awkward. I wanted to show that there is a different model for success. Being anxious, awkward, emotional, and vulnerable does not preclude you from having what you want. I wrote the book because I didn’t think anyone was sending that message out.

Being anxious, awkward, emotional, and vulnerable does not preclude you from having what you want.

I showed up to a panel the other night and I had on sneakers to get there and fancy shoes in my bag. When I went to change, I found that I had only brought one of the fancy shoes. [laughs] So I want to show that you can still be hapless, and that it’s OKAY. You don’t have to be “Inbox Zero.” I don’t understand airline miles. All these things that “successful” people have—I don’t have them.

The second part of why I wrote the book, is that I was watching the women who work for me who are a lot like me, who were projecting negative fantasies of themselves, and who lacked a fundamental education about business etiquette. People are thrown into careers right now and they don’t know how to deal with basic business etiquette. There are so many questions like, “How do I send an email without sounding neurotic?”

I wanted to deliver advice in a generous, loving way. Like, here, these are the basics. It’s much more simple than you think. Don’t get in your head. I really wanted to give this to women who might feel like it’s all too overwhelming.

One of the chapters is titled “Don’t Fake It ‘Til You Make It.” This is a favorite phrase of mine, so I have to ask—why shouldn’t we?!

Well first, I don’t think that we should misrepresent ourselves. In terms of faking your skills, I feel like there’s a really transparent world right now and you can be found out. For example, I see people who present themselves on their LinkedIn as a “political commentator” but they’ve only written one listicle on Bernie Sanders.

Also, you have value as precisely as who you are right now. So figure out what that value is rather than faking another value.

You have value as precisely as who you are right now. Figure out what that value is rather than faking another value.

The last reason is, I am a terrible faker. It never went well for me. I’m not a good liar, I can’t fake! Misrepresenting yourself will never work for you.

I’d love to ask you for some advice on something I’ve struggled with as the founder of a business. How do you say “no” to people when you’re someone who is so used to saying yes, or wanting to make sure everyone feels great and welcomed?

Well, I think there is a gentle way to say “no.” I think we’re so nervous to say “no” that sometimes we say “no” more aggressively than we have to. Or the opposite: we are overly apologetic.

I think being realistic of your time is one of the most important things for self-care. I’m very honest in these situations and I say, “I can’t do this right now, this sounds interesting, but I’m not in a place to do this right now.” I let them down easy and say that maybe there’s an opportunity in the future, and maybe we can check back in in six months. You can also steer somebody in somebody else’s direction. So the redirect is a kind way to let someone down. Saying, “Have you thought about this…?”

There’s a quote from a recent interview you did that spoke to me. You said, “I was [also] seeing that there was this expectation of what a successful woman looked like. She was polished and poised and blown-out and blazered, and it didn’t feel like me.” Do you think that this type of expectation is changing, slowly?

I think that’s my hope. I think we need to get away from this model of success porn. That success is sexy and perfect! It’s an image of success that men have put on us, in a way. It can’t be that the only way that you can show up to a professional situation is if you spend four hours getting ready that morning. Men don’t have to do that! That is not equality. That you have to pay $300 for a glam squad to get you suitable for public consumption is garbage! And we have to get away from it.


Let’s talk about your new role at Shondaland. I read that Shonda Rhimes emailed you about the job, and you met with her. What was it like getting that first meeting with Shonda?! She’s such a force.

Well, I mean the only reason that I was able to maintain any sort of composure is because I really didn’t think I wanted a job. I had just spent a year off work writing a book. And I had kind of, in my mind, thought “I think I’m done with internet content” and I’ll maybe teach or pitch another book, etc. It was like a fantasy life and new path that I was going down. So I wasn’t desperate for the job because I had this other plan in my mind.

It was only once I got in her presence that I got unbelievably excited, unbelievably engaged, and only until then did I feel that OMG, I must have this job. She lived up to every expectation that I had of her.

What lessons did you learn while at HelloGiggles that have shaped how you view your new role?

I think that I maybe was a little unwavering about my point of view or my instinct on things. I think that something like editorial quality and voice can be so subjective that people can try to argue you out of it. I’ve now been doing this for so long that now I can start trusting myself.

For the first time, I feel competent. And that’s just not a posture I’m putting on. And that only came from years of doing a thing, you know? I can trusting my instinct on things, and I’m not going to question things as much.

What is your vision for Shondaland and what can we expect?

I think that you can expect an inclusive place that’s highlighting the issues that are important to women, women of color, and progressive men. I think that we will be highlighting voices in culture, politics, activism, tech and entertainment that we find compelling. We want to highlight people that are really making a difference in the world right now. But also, we’ll be really intimate and funny and talk about the things that are happening to us. This is a really critical time and I feel like a lot of people feel helpless. We want to be a gathering place for people to talk about these things.


Let’s talk about self-care for a bit. What does self-care mean to you?

I need to be spacious with myself. I’m ultimately an introvert. I need lots of time to just be quiet. That took me a long time to learn. I was being really social because I thought that was what I needed, but I really needed more time to go in.

How do you practice self-care?

I try to get still and centered as much as possible. Just standing still and closing my eyes. I also do exercise more than I ever had. I take a lot of baths. It’s embarrassing. Maybe once a night. I take a nightly bath. I’ll just sit in there for a very long time.

What would you like your personal legacy to be?

I want to help a lot of people. I want to help people feel better than they think they are. I want them to know that it’s okay, and I want them to know that they can do it.

That’s what I bring to my day-to-day life with the people who work for me. I try to be selfless with the people I’m mentoring. Ultimately, that’s why I wrote the book. I wrote the book I wish I had.

As told to Alisha Ramos in June 2017. Lightly edited for clarity and conciseness. The book “Weird in a World That’s Not: A Career Guide for Misfits, F-ckups, and Failures” is available for purchase on Amazon.

Photos by Oriana Koren.