Workplace Weirdo? Shondaland Exec Pens Guide to Embracing Office Awkwardness


It's a small world when you're a weirdo. You think you're the only oddball, everyone else is normal and everyone but you has their acts together. How do you survive in a world where everyone else just seems to fit better than you do?

You don't.

Surviving in this world is a farce, because in fact, no one has their shit together, and nobody is perfect. You are not alone as a weirdo, and there are millions of “others" out there looking for a way to make it in their field, warts and all. Landing on your feet is possible. You merely need some social tools and how-to's to get there.

Enter Jennifer Romolini, former Editor-in-Chief at HelloGiggles, current Chief Content Officer of shondaland.com, and author of summer's break-out guide, Weird in a World That's Not: A Career Guide for Misfits, F*ckups, and Failures.

“I was always kind of socially awkward, physically clumsy, just kind of out of step," recalls Romolini, not-so-fondly remembering the years when she felt out of sync with the world. “My understanding of the world in a sensory way - understanding where my limbs were in space, has never been the best."

Characterizing herself as a youngster who was overly-emotional, sensitive and intense, Romolini looks back at why it was so difficult for her to navigate social channels and situations. Indeed, these characteristics would become the most lucrative traits for her going forward as she situates herself into the world of business.

“I always felt like I was wired a little differently," she remarks, laughing at the fact that there has been no point in her life through which she has glided. She has instead stumbled, and has been in a constant battle with herself and with societal mores she didn't quite fit into.

For her, the business world was a large, unreadable yet inescapable black hole where she felt out-of-sorts and underrepresented. “What I didn't see in the business world was an example of someone like me," she said. "It was as if once you became successful, you became this sort of poised mannequin. I didn't find that was happening to me, no matter what level of success I achieved."

So where exactly does a socially awkward, anxious, weirdo fit in amongst the poised busy-bodies of today's working elite? Ultimately, Romolini would seek to help those like her, who are attempting to rise up through the ranks without fitting in seamlessly, after she herself makes massive strides in a niche and difficult career.

“I was afraid to admit I wanted to be a writer," she recounts. She explains how coming from a working class, Italian-American background, the concept of a creative career was almost alien to her. She even goes so far as to say she couldn't visualize what life would be like as a writer.

She began checking off the boxes, reconciling herself with other jobs that might be more fitting or stable. She would, however, keep coming back to that which was alien, and says, "I finally figured out that I wanted to be around writing some time in my late twenties."

Jennifer Romolini.

After a few years waitressing, Romolini would kick start her writing career, and enjoyed a lengthy and lucrative stint in the publishing industry before becoming the EIC and Chief Content Officer at Zooey Deschanel's HelloGiggles in 2014. During the two years she was at the site that runs on quirky rhetoric and integrated weirdness, she grew the site's readership by 500 per cent.

It was during her time at HelloGiggles that she became faced with the creative career dilemma once again. She had an idea for a book: one with gravitas, spunk and a clear and positive voice. A book for the "weirdos, misfits and fuckups" of the world.

“I think it's hard to embrace entirely that you want to be solely a creative person"

-Jennifer Romolini

Having addressed and guided millennial women during her post there as EIC, she had become accustomed to the struggles they were facing and how they were viewed by the wider populace. "Millennial women were getting a bad rep," she says, continuing "I felt they were being told they were spoiled and entitled, and I didn't think that was true. But I felt like what they needed was someone to reach out and tell them: 'you're missing key points about how to survive in the business world.'"

It was not merely the readership of HelloGiggles that would inform her guide, however, as her daughter was also steadily creeping toward an age where she too would have to hop on the business ladder. “How do I teach her to be in the world, and to navigate the systems and authority without breaking her spirit?," she remembers asking herself. Ultimately, she would decide that it was a question that needed answering, and it would mean leaving her post at HelloGiggles to do so. “I wanted to give very solid advice while acknowledging that it was really hard to do, and you might not get it right the first time," she says. “I was still really scared to quit my job, but I did. I left the job behind to write the book. I made that decision and it was very terrifying."

Romolini took eight months off to pen the guide and in the midst of finishing her edits, she received an unexpected cold email from the one and only Shonda Rhimes about a job offer at Shondaland. “You can strategize all you want. You can white knuckle your career, but you never know what's going to happen," she asserts. And thus, Romolini had her next career turning point, at the helm of what she says will be a site for "really compelling stories - a special place that's not chasing social news traffic."

So instead of worrying about asking for a raise, leaving a shitty job, speaking up in meetings, ambition, or being a leader, Romolini gifts you the tools you need to execute and exceed in all of the above in her "soup to nuts guide." Given her proclivity for the weird and wonderful, but also her simultaneous success, we'd put our weight behind Romolini's book becoming a 2017 bestseller and a future go-to for all the world's up-and-coming misfits wishing to make waves and a name for themselves in the mainstream business world.

Weird in a World That's Not: A Career Guide for Misfits, F*ckups, and Failures is in stores now, and can be purchased online here. Portraits by Oriana Koren.

6 Min Read

All My Life I've Had To Fight

I live the pain and stress of being black in America every day: I am a black woman, the mother of a black son, sister to black men, and aunt to my black nephews. I remember what it was like as a young girl to be afraid to go to Howard Beach for fear of being chased out. I know what it's like to walk on Liberty Avenue and be called "nigger" and being so young that I didn't understand what the word meant, I had to ask my mother. I know too well that feeling in the pit of your stomach when a police car pulls up behind you and even though you know you haven't done anything wrong you fear that your life may be in danger from what should be a simple encounter. Like all African Americans, I am tired of this burden.

African Americans have a long history of having to fight for our humanity in America. We have had to fight for freedom, we have had to fight for equality, and we have had to fight for our lives. The fight continues to go on. I have often quoted that line from the character Sophia in Alice Walker's The Color Purple, "All my life I had to fight." When I say this to my white counterparts it can sometimes be uncomfortable because it's clear that they just don't get it. They view it as melodramatic. But it's not. It's part of the black experience, and it is the part of the black experience that black people don't want.

I have often quoted that line from the character Sophia in Alice Walker's The Color Purple, "All my life I had to fight."

While I was out yesterday, passing out PPE and talking to people, a woman asked me, "What is it going to take for this to change?" I told her that I think peaceful protesting is a good start. But it's just the start. We can't elect the same people for the past 20-30 years, some in the same positions, and then talk about how nothing has changed in the past 30 years.

This injustice, inequality, and inequity will not spontaneously disappear. It will take bold, outspoken, and fearless leadership to eradicate the systemic racism in our country. We must address the violence at the hands of a police force paid to serve and protect us. We must address the recurring experience of black people being passed over for a promotion and then being asked to train the white person who was hired. We must address the inequities in contract opportunities available to black businesses who are repeatedly deemed to lack the capacity. We must address the disparity in the quality of education provided to black students. We must address the right to a living wage, health care, and sick pay.

While we like to regard the system as broken, I've come to believe the system is working exactly as it was meant to for the people who are benefiting from it. We need a new system. One that works for all of us. I am running to become the mayor of New York City because I can't assume there's another person who has the courage to do the work that needs to be done to create a fair and just city.

We can't elect the same people for the past 20-30 years, some in the same positions, and then talk about how nothing has changed in the past 30 years.

There are some things we may not be able to change in people, but at this moment I think that whether you are black, white, purple, or yellow we all should be looking internally to see what is one thing that you can do to change this dynamic. Here's where we can start:

If we want change, we need a total reform of police departments throughout this country. That is going to require taking a hard look at our requirements to become a police officer, our disciplinary procedures when civilian complaints are filed, and a review of what and how we police. No one deserves to lose their life based upon the accusation of carrying counterfeit cash. We also need to hold police officers accountable for their actions. While it is their duty to protect and serve they should not be above the law. Even at this very moment, police officers are overstepping their boundaries.

If we want change, we have to build a sense of camaraderie between the police and community. A sense of working together and creating positive experiences. We have to be honest about the fact that we haven't allowed that to happen because we have utilized our police department as a revenue-generating entity. We are more concerned with cops writing tickets than protecting and serving. Even during these moments of protest we are witness to the differences made when the police supported the protesters and stood hand in hand with them or took a knee. It resulted in less violence and more peaceful protest. People felt heard; people felt respected; people felt like they mattered.

While we like to regard the system as broken, I've come to believe the system is working exactly as it was meant to for the people who are benefiting from it. We need a new system.

If we want change, we have to be willing to clean house. And that means that some of you are going to have to step up to the plate and take roles of leadership. In my city alone, there are 35 city council seats that are term-limited in 2021. There are some that aren't termed but maybe their term should be up. Step up to the plate and run. If nothing else it will let our elected officials see that they need to stop being comfortable and do more. We don't need you out in the street taking selfies or reporting the problems to us. We need solutions. We need you in a room implementing policies that will ensure that these things don't continue to happen.

If we want change, we need to support grassroots candidates that are not in corporate pockets, who are not taking PAC money, and who really want to make a difference to their community. We need candidates that know first-hand and can relate to the experiences that many of us are going through.

We are at a pivotal moment. It is inspiring to see people from all races and backgrounds in the streets protesting, standing up for justice, and wanting to see change. We must seize this moment, but we must also be mindful that change requires more.

People often ask me why I decided to run for office? I am running for me. I am running for the little girl that was called nigger on Liberty Avenue. For the woman who has been pulled over for no reason. For my nephew who was consistently stopped during the era of stop and frisk. I am running for your son, your brother, and your nephew. I am running so that the next generation will never have to say, "All my life I had to fight." Because although we won't stop until we see justice and changes that address inequality and inequity effectively, this fight is exhausting.