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, 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.