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.

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Do 2020 Presidential Candidates Still Have Rules to Play By?

Not too many years ago, my advice to political candidates would have been pretty simple: "Don't do or say anything stupid." But the last few elections have rendered that advice outdated.

When Barack Obama referred to his grandmother as a "typical white woman" during the 2008 campaign, for example, many people thought it would cost him the election -- and once upon a time, it probably would have. But his supporters were focused on the values and positions he professed, and they weren't going to let one unwise comment distract them. Candidate Obama didn't even get much pushback for saying, "We're five days away from fundamentally transforming the United States of America." That statement should have given even his most ardent supporters pause, but it didn't. It was in line with everything Obama had previously said, and it was what his supporters wanted to hear.

2016: What rules?

Fast forward to 2016, and Donald Trump didn't just ignore traditional norms, he almost seemed to relish violating them. Who would have ever dreamed we'd elect a man who talked openly about grabbing women by the **** and who was constantly blasting out crazy-sounding Tweets? But Trump did get elected. Why? Some people believe it was because Americans finally felt like they had permission to show their bigotry. Others think Obama had pushed things so far to the left that right-wing voters were more interested in dragging public policy back toward the middle than in what Trump was Tweeting.

Another theory is that Trump's lewd, crude, and socially unacceptable behavior was deliberately designed to make Democrats feel comfortable campaigning on policies that were far further to the left than they ever would have attempted before. Why? Because they were sure America would never elect someone who acted like Trump. If that theory is right, and Democrats took the bait, Trump's "digital policies" served him well.

And although Trump's brash style drew the most handlines, he wasn't the only one who seemed to have forgotten the, "Don't do or say anything stupid," rule. Hillary Clinton also made news when she made a "basket of deplorables" comment at a private fundraiser, but it leaked out, and it dogged her for the rest of the election cycle.

And that's where we need to start our discussion. Now that all the old rules about candidate behavior have been blown away, do presidential candidates even need digital policies?

Yes, they do. More than ever, in my opinion. Let me tell you why.

Digital policies for 2020 and beyond

While the 2016 election tossed traditional rules about political campaigns to the trash heap, that doesn't mean you can do anything you want. Even if it's just for the sake of consistency, candidates need digital policies for their own campaigns, regardless of what anybody else is doing. Here are some important things to consider.

Align your digital policies with your campaign strategy

Aside from all the accompanying bells and whistles, why do you want to be president? What ideological beliefs are driving you? If you were to become president, what would you want your legacy to be? Once you've answered those questions honestly, you can develop your campaign strategy. Only then can you develop digital policies that are in alignment with the overall purpose -- the "Why?" -- of your campaign:

  • If part of your campaign strategy, for example, is to position yourself as someone who's above the fray of the nastiness of modern politics, then one of your digital policies should be that your campaign will never post or share anything that attacks another candidate on a personal level. Attacks will be targeted only at the policy level.
  • While it's not something I would recommend, if your campaign strategy is to depict the other side as "deplorables," then one of your digital policies should be to post and share every post, meme, image, etc. that supports your claim.
  • If a central piece of your platform is that detaining would-be refugees at the border is inhumane, then your digital policies should state that you will never say, post, or share anything that contradicts that belief, even if Trump plans to relocate some of them to your own city. Complaining that such a move would put too big a strain on local resources -- even if true -- would be making an argument for the other side. Don't do it.
  • Don't be too quick to share posts or Tweets from supporters. If it's a text post, read all of it to make sure there's not something in there that would reflect negatively on you. And examine images closely to make sure there's not a small detail that someone may notice.
  • Decide what your campaign's voice and tone will be. When you send out emails asking for donations, will you address the recipient as "friend" and stress the urgency of donating so you can continue to fight for them? Or will you personalize each email and use a more low-key, collaborative approach?

Those are just a few examples. The takeaway is that your online behavior should always support your campaign strategy. While you could probably get away with posting or sharing something that seems mean or "unpresidential," posting something that contradicts who you say you are could be deadly to your campaign. Trust me on this -- if there are inconsistencies, Twitter will find them and broadcast them to the world. And you'll have to waste valuable time, resources, and public trust to explain those inconsistencies away.

Remember that the most common-sense digital policies still apply

The 2016 election didn't abolish all of the rules. Some still apply and should definitely be included in your digital policies:

  1. Claim every domain you can think of that a supporter might type into a search engine. Jeb Bush not claiming www.jebbush.com (the official campaign domain was www.jeb2016.com) was a rookie mistake, and he deserved to have his supporters redirected to Trump's site.
  2. Choose your campaign's Twitter handle wisely. It should be obvious, not clever or cutesy. In addition, consider creating accounts with possible variations of the Twitter handle you chose so that no one else can use them.
  3. Give the same care to selecting hashtags. When considering a hashtag, conduct a search to understand its current use -- it might not be what you think! When making up new hashtags, try to avoid anything that could be hijacked for a different purpose -- one that might end up embarrassing you.
  4. Make sure that anyone authorized to Tweet, post, etc., on your behalf has a copy of your digital policies and understands the reasons behind them. (People are more likely to follow a rule if they understand why it's important.)
  5. Decide what you'll do if you make an online faux pas that starts a firestorm. What's your emergency plan?
  6. Consider sending an email to supporters who sign up on your website, thanking them for their support and suggesting ways (based on digital policies) they can help your messaging efforts. If you let them know how they can best help you, most should be happy to comply. It's a small ask that could prevent you from having to publicly disavow an ardent supporter.
  7. Make sure you're compliant with all applicable regulations: campaign finance, accessibility, privacy, etc. Adopt a double opt-in policy, so that users who sign up for your newsletter or email list through your website have to confirm by clicking on a link in an email. (And make sure your email template provides an easy way for people to unsubscribe.)
  8. Few people thought 2016 would end the way it did. And there's no way to predict quite yet what forces will shape the 2020 election. Careful tracking of your messaging (likes, shares, comments, etc.) will tell you if you're on track or if public opinion has shifted yet again. If so, your messaging needs to shift with it. Ideally, one person should be responsible for monitoring reaction to the campaign's messaging and for raising a red flag if reactions aren't what was expected.

Thankfully, the world hasn't completely lost its marbles

Whatever the outcome of the election may be, candidates now face a situation where long-standing rules of behavior no longer apply. You now have to make your own rules -- your own digital policies. You can't make assumptions about what the voting public will or won't accept. You can't assume that "They'll never vote for someone who acts like that"; neither can you assume, "Oh, I can get away with that, too." So do it right from the beginning. Because in this election, I predict that sound digital policies combined with authenticity will be your best friend.