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June 1, 2017

Editor's Choice: Weird in a World That's Not: A Career Guide for Misfits, F*ckups, and Failures

By: Dylan Schleicher @ 2:59 PM – Filed under: Big Ideas & New Perspectives, Biography & Narrative, Personal Development & Human Behavior

Weirdworldthatsnot

Weird in a World That's Not: A Career Guide for Misfits, F*ckups, and Failures by Jennifer Romolini, Harper Business, 304 pages, Hardcover, June 2017, ISBN 9780062472724

We prefer our success stories neatly packaged, linear and straight. We like envisioning that kind of success because that’s the version we think we would like for ourselves—uncomplicated, struggle- and drama-free. But, those stories are boring. It’s when it gets a little weird that it gets really entertaining.

Jennifer Romolini’s story, told in her new book and career guide, Weird in a World That's Not, is anything but boring. It is as much a memoir as a book on how to make it in your own career, and it is punctuated by beautiful, poetic, funny, heartbreaking and inspiring prose. For instance, speaking of the time she spent living with her first husband in a hotel for business travelers, working in the hotel restaurant and nannying for the General Manager’s kids from California in a hotel suite on the hotel’s twenty-second floor, she writes:

 

We were all strangers and nomads. The hotel restaurant revolved. Everything felt unmoored, like one day we could all float away.

 

It was not her first waitressing job. That was at a roach-infested Mexican restaurant in a strip mall owned by two Indian men whose empathy and positivity informed her management style later on. It was her first real job after failing out of college and being cut off financially by her parents, and waitressing would be her main source of income fort he next seven years. They were not wasted years. They gave her confidence and “a semblance of grace,” and provided lessons that would prove to be crucial for her later: 

 

For the most part, you get what you put into waitressing—the more you hustle, the more money you make. Waiting tables became the foundational education for everything I’d do in my professional life. The constant multitasking, the precision necessary to execute a meal, learning to perfect my timing and collaborate with a team—these were lessons I’d carry with me for years, and even use today. The family feeling of a restaurant, the feeling that you are all in it together, because you have to be, because you need each other to get the work done, is an apt model for team building in office jobs.

 

And as she worked her way up into steadily fancier restaurants, she gained an understanding of the well-heeled patrons of those places and learned how to dine in places like it, which would also help her later in her career. 

But making that leap is not the rah rah tale you might expect in a book about success. It is full of self-doubt and loathing, awkwardness and nervousness, and constant striving and overcoming.

The first thing she decided to do is head back to school with an aim of getting a job in some sort of publishing. And while the story is exhilarating, it isn’t ever easy:

 

You shed skin, and you shed comfort. You shed what you know. […] Which means that for many of us, discovering our dreams, or even the next step to achieve success, feels less like an obvious, meant-to-be golden road laid out before us and more like an excavation of fear.

 

Okay… are you pumped yet!?

When she tells you it’s just as instructive to listen to your bad feelings and “follow them to their origin”—to let your jealousy and anger and envy of others lead you toward discovering what you want to do—it sounds awful. But, if you can let them inform you and engage you in creating your own life anew, then those bad feelings will cease to engulf you. And it comes with some incredibly open-eyed, practical advice on deciding what you want to do next:

 

Don’t say you’re too old, don’t say it will take three years and by the time you’re done you’ll be twenty-six, or thirty-four, or forty-one. Barring some seriously bad shit, you’ll turn twenty-six or thirty-four or forty-one anyway. You’ll feel a lot better about yourself if you accomplish something in those years, rather than staying stuck where you are right now.

 

She’ll lead you to the questions you need to ask yourself, give you real-world, hold-the-bullshit advice on constructing a résumé, and how to interview (Romolini went on twenty-three before landing her first job in publishing):

 

First, don’t fake it until you make it. Sure, fake feeling more confident than you do, fake using a real-person voice when you want to use a robot voice, fake that you know what to do with your hands. But, in interviews especially, it’s crucial that you accurately represent what it is you can and cannot do. […] Don’t oversell yourself. A smart boss will see right through it and will not hire you; a less smart boss will believe you and expect you to flex those skills on day one, and you will start your job on the wrong foot and perhaps never recover. You have merit as precisely what you are at this moment. Stick with that.

 

She lost that first job six months later when the company failed. That’s right… just as she thought she had escaped her own history of failure, the company she found herself in failed. And then two more after that. But instead of returning to waitressing, she opted for another often thankless job—freelance fact-checking—for two years before she found another full-time job in publishing. And, just like her days working in restaurants, that work taught her a lot:

 

Fact-checking taught me how writers found and pulled stories together. It taught me how stories fell apart and what you needed to keep them from getting killed.

 

And the entire time she was doing this during the day, she was writing stories and pitching them everywhere she could at night. And she eventually landed in a full-time position.

Most of all, she’ll teach you how to embrace your weirdness in the workplace, and overcome the awkwardness that accompanies working in the bizarre land of corporate America. She’ll also get super basic and tell you things about professional life like how to engage in small talk (providing one of the best lines in the book, “You may go weird, but you don’t have to go home.”), how to write an email, and how to drink in a professional setting. One of the recurring lessons she offers is that others aren’t obsessing over how odd you are, as this tidbit on meetings reflects:

 

Last thought on meetings—and this is super-important to realize as you enter more and more business situations—no matter how heart-thumpingly anxious you feel, no one knows how weird it feels inside your head. As long as you don’t say “Let’s burn this motherfucker down!” or run through the room wearing zero pants, no one is noticing all your weird quirks. Everyone is distracted by their own stuff.

 

She gets into more profound issues like how to own your ambition so that you don’t come off as entitled. And, yes, she’ll tell you how to ask for a raise. But she’ll also help you determine when and if you really deserve one, and when to quit.

I think the lesson to take away from the book is pretty simple: accept and get over yourself, be yourself, be honest, work hard, get good at what you do, be kind and active (rather than passive and passive-aggressive), and get shit done. But Jennifer Romolini makes that lesson personal and entertaining. She’s blunt. She swears a lot. She will tell you why Leslie Knope is the only reliable role model for women bosses on TV, and what was wrong with “the formative career movies of her youth.” She says boldly obvious things like:

 

The reason we rarely see great female leadership on film is because the world is sexist …

 

While also being more nuanced about it and reflecting that it’s also “because being a good leader isn’t actually all that glamorous, exciting, and entertaining,” and that “most people aren’t that good at it.” She acknowledges the seriousness and importance of leadership experts and leadership books, and then gives you her real-life tale of leadership and the mistakes she made along the way before acknowledging what she says is the hardest sentence for her to write in the book:

 

Over the years, I’ve become a great fucking boss.

 

And then she tells you how to be a good boss—a brave boss­—how to hire and fire people, how to interview and give productive feedback. It all comes across as common sense, because it is. But it is hard won and perhaps counterintuitive in a business world full of jargon and appearances. There is none of that in Romolini. It is all real, and it is all on display. She tells embarrassing and raw stories about herself and the jobs she’s had. She tells you how to deal with domineering, abusive men in the workplace—simply and straightforwardly and with spine—and about her experience as a mom who is also a boss and a business person. She gives great advice from the perspective of someone struggling to make it, and from the perspective of someone who has made it—who is now literally a boss—and wants desperately to help you do the same. And she does it in a way that makes you understand and empathize with both.

Listen: I am a thirty-six year old man who really enjoys reading books on socioeconomics and foreign policy and psychology, on the history of banks and business and baseball and politics and people. Jennifer Romolini’s Weird in a World That's Not is a book written with an audience of young, still-somewhat uncomfortable-in-their-own-skin women just entering the workforce in mind. It’s largely about building a career and being a boss—things I’m not all that interested in reading about. And it’s my favorite book at the moment, my favorite book of the year so far.

It’s funny and idiosyncratic and irreverent and inspiring and satisfying and honest. I wish I could have read this book tens years ago. I want to read it again ten years from now. And I hope a lot of other people choose to read it.


About Dylan Schleicher


Dylan Schleicher has been a part of the 800-CEO-READ claque since 2003. Even though he's stayed on at the company, he has not stayed put. After beginning in shipping & receiving, he joined customer service and accounting before moving into his current, highly elliptical orbit of duties overseeing the ChangeThis and In the Books websites, the company's annual review of books and in-house design. He lives with his wife and two children in the Washington Heights neighborhood on Milwaukee's West Side.