Growing up, Jennifer Romolini knew she was “weird.” But as a broke college dropout who was waiting tables in her late twenties while peers climbed the career ladder, that feeling of being an awkward, uncool outsider was magnified. So how did Romolini go from being the girl who didn’t have her shit together to being the girl who was actually running shit? In her new book, Weird in a World That’s Not: A Career Guide for Misfits, F*ckups, and Failures, she explains exactly how.
Like Romolini herself (who, full disclosure, I have known personally for several years and whose husband also works at MTV News), Weird in a World That’s Not is unconventional. Yes, it offers smart, practical advice, from dealing with horrible bosses to how to ask for a raise, but the shondaland.com chief content officer (and former editor-in-chief of HelloGiggles) also offers handfuls of squirm-worthy, reassuring, and honest anecdotes about how it really feels to be a sweaty, insecure mess while attempting to figure it all out. The good news? Even if the sweatiness and insecurities never completely go away, they don’t have to get in your way as you head to the top of whatever career ladder you’re climbing.
Over coffee in Los Angeles, I sat down with Romolini to discuss the biggest misconceptions of achieving success, the suckiest (and best) parts of being a boss, and what it’s like working for Shonda Rhimes, queen of TV.
From Sophia Amoruso’s #GIRLBOSS to Sheryl Sandberg’s Lean In: Women, Work, and the Will to Lead, there’s been an undeniable rise in career books for millennial women over the last few years. That being said, what inspired you to write Weird in a World That’s Not and what makes your book different from the other self-help books on shelves?
Jennifer Romolini: I wrote the book for two different reasons. One, because I was still experiencing a lot of anxiety and awkwardness and I felt like I didn’t fit into the shell of what “success” looked like. I didn’t feel polished and poised and blown-out perfectly in the way that all pictures of success looked like to me. The book was for me. Why do I feel so awkward? Why do I still feel like I don’t belong in this situation? I wanted to show a different kind of picture of success. And it wasn’t all, “Oh, you’ll overcome all this awkwardness and weirdness and emotional messiness and your slacker tendencies,” but that you could just be successful as who you are.
But the second thing was that I was seeing [in] the people who worked for me — who were mainly millennials at that point — that there were some fundamental things about working that they hadn’t been taught. There’s a real lack of mentorship specifically in offices right now because everything moves so fast. You jump from one thing to another and there’s no apprenticeship. There [are] no assistants anymore — or not as many. Things go too fast, so you miss out on the very basics of working: how to send an email, how to deal with networking, how to ask for a promotion. And sure, those things are common sense, but if you’re overthinking, very emotional, and sensitive, the common sense sometimes goes out the window and you just need someone to tell you how to get from A to B in a very specific way.
You went from being a college dropout to overseeing some of the biggest websites on the internet. As someone who didn’t have the fancy connections or the classic “overachiever” characteristics, how did you navigate your way to the top?
Romolini: Clumsily. Slowly. Awkwardly. I had a lot of humility. I didn’t have confidence so much as I forced myself to be brave. I didn’t turn down opportunities. Even if something seemed like, “Oh, I don’t know that business magazine — ew” or “I don’t know about that tech company. That’s not glamorous. That doesn’t seem sexy to me” — I still didn’t turn it down. I explored everything that was presented to me. I think that we get in our mind this idea of what our career should look like and they wind up looking very different from that. It’s having that flexibility and saying, “Well, maybe I don’t know exactly what I need here” and just sort of following what’s presented to you.
I also worked really hard. I gain a lot of pleasure by working hard and being good at what I do. I think that’s really why I’m successful. It’s as simple as that.
One of the things I really admired about your book was that you didn’t shy away from opening up about your fuckups and failures. Was it scary to write so vulnerably?
Romolini: Yes. I mean, I cried most of the time when I was writing this book. That’s the truth about writing a book: You cry a lot.
I wanted [the book to be]: I can relate to you. There is no fuckup you can have that I have not had. I was lazy at certain points in my life and lost and insecure and angry and putting my bullshit on other people. I wanted to own all of that. I wanted to own how I sabotaged and how I had self-doubt and places where I was inappropriate — all of my stumbles. We need to talk about that more. It’s like you’re supposed to start and end up in this perfect, shiny place. And I don’t think a lot of people are being honest about the road in between and just how disgusting you feel.
How do you define success?
Romolini: I feel content and I feel competent. For me, that’s the definition of success. I don’t always feel happy, but I feel mostly content with the choices I’ve made in my life and I feel competent at what I do. I can add a third “C” here: I feel challenged. And I think those three things make up success more than, “I’m happy! I have a lot of money! I have a big title!” Those things are just sort of bullshit. I’m very much interested right now in being a person — not a persona. Contentment, competence, and challenge really fulfill me more than anything else.
What do you think are the biggest misconceptions about achieving success?
Romolini: Well, it sucks being a boss. Nobody talks about that. It’s way more stressful, way lonelier, and it’s not as much fun. The truth is, the chase and the way up [to the top] is really fun. There’s a lot more camaraderie and, “Oh, I’ve never done this before!” or “This is the first time — it’s so exciting!” That freshness — you can’t get that back.
What you can get on the other side — if you’re smart and you make it a priority to be generous — is that you can give that to other people. You can give kindness back and mentorship, which can bring satisfaction when you’re more successful. I get a lot of satisfaction out of that. But nobody talks about how, like, it’s not fucking fun to be the boss and having to be a dick all the time.
What makes a good boss?
Romolini: I mean, I don’t know if I’m allowed to say the word “dick” —
Romolini: But going back to what I was saying to that “dick reality,” which is you can’t be people’s friends. You have to be their boss. You have to give them clear assignments and clear boundaries. When they fuck up, you have to tell them that they’re fucking up — not with aggression, but because that’s the way work gets done. You need to zero in on each individual employee’s strengths and weaknesses and have them know at all times that you’re there for them and interested in their career path. Because that’s when employees perform the best — when they know that you’re in it together and, also, that they’re going to grow by working with you.
On the flip side of that, what should you do if your boss sucks?
Romolini: If your boss sucks, you’re in a different position because you’re not gonna learn from the boss. You need to learn what in the job you can learn before you move on. So what kind of job do you want next and what skills or title or projects do you need to work on before you can get out of the situation? When your boss sucks, you need to overmanage your boss. It’s just like if you have a parent that sucks and you end up being the parent to your parent. You wind up filling in the gaps, but you have to overmanage. You have to feed them “I’m doing all of this and this” and get them off your back. And create boundaries. That’s like the magic word, but you really can do it and say, “You know what? I’m sorry, I can’t work until 8 p.m. tonight.” And if you’re a competent person and you get fired, it’s worth it to get fired anyway because you don’t want to be in a situation where you’re being abused.
One of the chapters in your book is titled, “Don’t Fake It Until You Make It,” which is interesting, because we’re often told the opposite — that we should be faking it until we make it. What do you mean by this?
Romolini: We’re in a situation now in the world of social media and online networking where we can basically create whatever we want — whatever profile we want. We can turn a couple of listicles about Bernie Sanders into “I’m a political correspondent.” We can be a brand. But what happens is, if you’re faking, somebody is going to figure it out at some point. And you don’t want to be figured out. It’s embarrassing, it’s going to do you no good, and it’s going to piss people off.
I also say “don’t fake it until you make it” because I’m a terrible faker. It wasn’t totally an option for me, but every time I stretch the truth, every time I tried to pretend I was competent in a way that I wasn’t, it backfired for me. I think that there are ways to fake it. If you’re really anxious, you should fake that you’re not anxious. But in terms of faking your skills or even just pretending to be something you’re not, I think you’re going to have the most rewarding professional experiences when you’re your authentic self.
In what ways have you changed the most since your early twenties? In what ways have you stayed the same?
Romolini: I’m not as angry as I used to be. I was really just pissed off. I was jealous and angry and I think that fueled a lot of my need to succeed because I really had a lot to prove. I had a chip on my shoulder. I definitely shook a lot of that.
I think the way in which I’m the same — I know the way in which I’m still the same — is that I’m compulsively honest, which got me into trouble when I was younger, but doesn’t get me into trouble as much now. Now it’s actually kind of an asset to be a boss who’s compulsively honest. It’s less of an asset to be a junior employee who is compulsively honest. So different qualities will work to your advantage at different points in your life.
Let’s say that there’s a twentysomething who’s grinding away at her job and she wakes up one day and decides that she hates it. She wants out, but feels like it’s too late to start over with a career that’s completely different. What would you say to her?
Romolini: Well, first off, I really believe that it’s never too late. To the person in their twenties, I would say that I was waiting tables until my late twenties. If you don’t like what you’re doing, start to explore what you do like to do and then everything becomes very systematic. It becomes very much like, “OK, let’s look at this in a very organized way and take my emotions away from it. I don’t want to do this anymore, but I may want to do one of these three things.” What do those things look like? How do you get training to do those things? What do you need to get from here to there? And just start doing it. People don’t go back to school and say, “Oh, I’ll be 30 by the time I graduate.” You’re gonna be 30 anyway. Why not?
Also, accept that in order to make a transition like that, you’re gonna have to give up something. You’re gonna have to give up money and time. You’re gonna have to give up comfort. But the end result of being in something that you actually love and can engage with — a career that satisfies you — is worth that couple of years of discomfort.
I want to go back to the idea of misconceptions. When we think about the qualities of powerful women, we’re not thinking of words like “awkward” or “anxious.” There’s a myth that these types of women don’t have these characteristics, or if they do have these characteristics, they can’t possibly become a boss one day. Why isn’t that true?
Romolini: I don’t know why everybody is afraid to admit it. I don’t know why everybody is afraid to admit that they get stains on their pants, or they sniff their shirts in the morning to see if they’re clean. I don’t know why there’s this “you’re going to be dragged off by security” fallibility.
I think that one of the ways that you become an amazing leader is by having empathy — that being honest about your feelings will help you get through all of this. So pretending to be a contained person — if you’re not a contained person — is not gonna work for you. I don’t know if those successful women are different than me or if they hide it better than I do, but I can’t hide it. That’s not who I am. Whatever you are, just be that. Don’t try to fit into the mold of what “success” looks like. Be who you are throughout the entirety of your career.
You recently took on a new role as chief content officer of shondaland.com. What’s it like working for the queen of TV?
Romolini: I mean ...
Romolini: Shonda [Rhimes] is such a compelling, smart, mighty woman. She’s such a woman of integrity. I really didn’t think I was going to go back into another content job and when I got the call from Shonda, I thought, OK, everything’s changed now.
What’s the best career advice you’ve ever received?
Romolini: I think the best advice I got — and she didn’t say this precisely like this — but Kim France [former editor-in-chief of Lucky magazine] at some point told me to slow my roll. And my roll needed slowing [laughs].
I also had somebody tell me that a little sugar goes a long way, but I hate that because it means you have be sweet. But I actually did need to be a little sweeter.
If you could go back in time and tell your 21-year-old self one thing, what would it be?
Romolini: Chill the fuck out.
You can find Weird in a World That’s Not in stores on June 6.