Introduction

I’m going to make a few assumptions about you. If I’m wrong, I hope you’ll read the rest of this book anyway. Also: I’m sorry for misreading you. If I’m right, well, I’m clearly some sort of wizard.

You look great, by the way.

Anyway, this is who I think you are. You’re smart. You’re talented. You’re ambitious. But you’re not “well-leveraged.” You don’t think you have an “edge” on the competition. You don’t have “hookups” that you can exploit. You don’t have a “stellar pedigree,” as if you are some sort of racehorse. You are not the spawn of a CEO and you can’t call upon the powers of nepotism when things aren’t “looking up.” You don’t “know” a lot of “people.”

You’re an outsider.

And your outsider status has made you a little uncomfortable. You’re not “sure of yourself” in a job interview. You don’t know how to “make a presentation” or “give a speech.” You’re not sure what to order when you’re at an “important lunch.”

You’re finding my use of quotation marks “kind of stupid.”

It’s important for you to know that all of those things describe me too. I’m pretty smart, kind of talented, and moderately ambitious, but when I unexpectedly (and, from my perspective, miraculously) got a call from Esquire magazine in 2005 to interview for an editor position, I felt crucially ill equipped for the job. I worked at Southwest Airlines’ in-flight magazine (the Esquire of airplane magazines), had a degree from the University of North Texas (the Harvard of the northeastern Texas / southern Oklahoma region), and knew sort-of-important people, but they were all in Dallas (the New York City of . . . eh, never mind).

I thought that my circumstances would determine my eventual failure in New York. Because I wasn’t the right type. And I didn’t deserve it. I was an impostor, and I was going to be found out about a month in. (Rule: Nothing can be found out about a person less than a month into a job. Nothing. Because you’re not seeing the real person. You’re seeing an agent for that person whose job it is to confusedly stare at the fancy electronic restroom faucets until someone comes along who knows how they work.)

The term “impostor phenomenon” was coined in 1978 by Georgia State University psychologists Pauline Clance and Suzanne Imes. Initially linked mainly to high-achieving women (but later seen as often—if not more so—in men), it can be broken down into three types of feelings: that you aren’t as successful as other people think; that your accomplishments can be chalked up to luck; and that even if you’ve attained success, it isn’t all that impressive.

Since that initial research, psychologists have studied and debated the possible causes of “impostorism.” Is it a trait or is it a state of mind? Is it a “situational condition” or is it deeply rooted in how we were parented? Is it merely a reflection of an anxious personality? Or depression? Are people who describe themselves as frauds actually more confident than they let on, as some researchers have suggested? Is it a “self-presentational strategy”—something that people do, consciously or not, to seem extra humble or to lower others’ expectations of them?

This book isn’t so concerned with why people feel like impostors but that people do.

And a lot of people do.

People like Supreme Court Justice Sonia Sotomayor: “My first month as a judge I was terrified. . . . I still couldn’t believe this had worked out as dreamed, and I felt myself almost an impostor meeting my fate so brazenly.”

And Kate Winslet: “Sometimes I wake up in the morning before going off to a shoot, and I think, I can’t do this. I’m a fraud.”

And Chuck Lorre, creator/writer/producer of The Big Bang Theory and Two and a Half Men: “When you go and watch a rehearsal of something you’ve written and it stinks, the natural feeling is ‘I stink. I’m a fraud. I need to go and hide.’”

And Alexis Ohanian, cofounder of Reddit: “I have no idea what I’m doing, and that’s awesome.”

And Tina Fey: “You just try to ride the egomania when it comes and enjoy it, and then slide through the idea of fraud.”

And Meryl Streep: “You think, ‘Why would anyone want to see me again in a movie? And I don’t know how to act anyway, so why am I doing this?’”

When I got to New York, I felt unlike all of my peers. I didn’t dress the part. I didn’t know anyone important. I didn’t know how to have a business lunch. I didn’t even really know how to order a drink in a bar. (At this point, you may be questioning my ability to clean and feed myself. Bear with me.) I didn’t know how to work at a big magazine and I didn’t know how to live in a city like New York.

But a few months after working in New York, a truth came into focus: Everyone around me was an impostor, too. We all have insecurities. And I think successful people are successful because of them. Not in spite of them. There’s great energy in the spot on the Venn diagram where awkwardness and ambition overlap. There’s a great energy in weirdness.

Hugely important rule: Everyone is weird and nervous. No matter how famous or important, everyone is just really weird and really nervous. Especially the people who don’t seem weird or nervous.

I came to see that the difference between those who are successful and those who aren’t isn’t just talent or behavior. The people I came to respect the most weren’t any better minds or workers than I was (though they were talented and hardworking, believe me). They were just better at seeming better. They acted like they belonged. They seemed to claim success by performing its mechanics with confidence.

And as I met more and more interesting people (from people in my industry to famous actors and musicians as a part of my job), I began to realize that most of the so-called rules of success don’t work. You don’t have to “sell” yourself. You don’t have to “network.” And you don’t have to dress the “right” way (although that has its advantages). But you do have to understand why people do those things. And you have to comport yourself with integrity, even when you have no idea what’s going on—in the meeting room, at a business lunch, or at the bar after work.

I also learned that the problem is not being ignorant of certain customs or devoid of certain skills. The problem is letting your inadequacies get to you.

This is a book about success, but my angle on success is a sideways one. I am not going to spell out any sort of “system” or “philosophy.” This is a self-help book for people who don’t like self-help books. It’s less concerned with how to “get” a job than how to interview for one. It’s less concerned with how to overcome a fear of public speaking than how to approach a podium. To borrow a now-overused construct from the military, this book is less concerned about strategy than it is about tactics. It’s not about the “what.” It’s about the “how” and the “who.”

This book is about the seemingly small things, which are important for three reasons: The small things can cause crippling anxiety when you don’t think you have a handle on them. (This kind of anxiety is totally unnecessary.) The small things are emblematic of greatness, signals to others that you are not messing around, code for integrity, dedication, and consideration. The small things are of huge practical importance—they’re what make other people feel comfortable around you, make an immediate impression, and cover up mistakes.

For my entire career, I’ve been obsessed with how the small things—from an amusing turn of phrase in a magazine story to a handshake at the beginning of a business lunch—are often the most memorable things and can add up to something very big. And important. And lucrative.

Impostorism is not something to overcome. It’s not something to “fake” your way out of. You can’t “fake it to make it.” No, you need to harness your fear to work for you. Embrace your outsider status. Embrace your mistakes. Success is about being a human being, not a drone. But in order to seem human you have to reckon with the small customs of professional life—even if you eventually reject their importance to you.

It’s possible to use small but meaningful moments to feel and seem comfortable even when you don’t think you belong.

But you do. Of course you do.

1

First, a Little Story

Monday, May 16, 2005

On the second floor of the northeast wing of a big office building in the middle of a nondescript business park in the suburbs between Dallas and Fort Worth, I arrived back at my desk after lunch. I was a young editor in chief of Spirit, the in-flight magazine of Southwest Airlines. My lunch was a number one value size from Chick-fil-A, eaten in my car while driving back to the office. My state was vaguely dissatisfied—both with my fried-chicken sandwich and with my job at an in-flight magazine in the suburbs of Dallas.

Placed conspicuously upon my keyboard was a message. There was the name of a person I didn’t recognize, the name of a media company I did recognize, and a New York phone number.

This was odd, because the company was Hearst—a major media corporation based in New York. Hearst owned Cosmopolitan, Marie Claire, Good Housekeeping, Popular Mechanics, Esquire, and lots of other “major newsstand” magazines.

So I called the guy back.

“I’m the recruiting director for Hearst Magazines, I’m looking for candidates for an open editor position, and I’d love to talk with you about it,” he said.

Which was a strange thing to hear. Now, I had a pretty good job. Of the nine or ten in-flight magazines in the United States, mine was certainly among the top, oh, seven. And at thirty, I was objectively successful. But while I was in the media, I was in a minor part of the media. If Esquire was the big dance, Spirit magazine was smoking pot behind the gym.

So it struck me as strange that the recruiter would want to talk to me. Turns out he had been on a Southwest Airlines flight from Philadelphia to Pittsburgh over the weekend, had pulled the in-flight magazine from the seatback pocket in front of him, had actually read it, and had thought that it wasn’t bad.

My first thought was “This could be big.” My second thought was “There’s probably been some mistake.” My third thought was “There’s definitely been some mistake.”

There’s a thing that happens to me when the odor of opportunity floats my way. It triggers a combination of giddiness and revulsion. (Outkast once remarked, “Don’t everybody like the smell of gasoline?” That’s how I feel about opportunity. Alternately pleasing and repellant.) Which describes my general state for the duration of the phone call. Over the course of about fifteen minutes, the recruiter asked me a lot of pointed questions about my career and my magazine. His end of the conversation was appropriately cryptic. Due to the general sense of discretion that aids in a recruiter’s work (as well as federal antidiscrimination laws that forbid certain kinds of questions during all job interviews), all screening conversations are like this.

After about twenty minutes of a one-sided conversation, I finally asked the recruiter a question.

“What’s this about?”

If you could somehow look at my brain’s thought log from that day, there would be a span lasting about two-thirds of a second in which there were forty-five instances of the thought, “Please say Esquire.”

“There’s a job at Esquire,” he said.

Now, because I am pathologically incapable of fully embracing an obviously positive professional development, likely due to a genetic defense mechanism inherited from a long line of humble, hardscrabble, frequently disappointed ancestors from Texas and Kentucky, I immediately thought that the whole thing was a scam. An involuntary psychological girding occurred. The odor of opportunity became a stench. I typed “magazine hiring scam” into Google. This situation was a little too Trading Places–esque for my liking. This guy was Don Ameche, the editor in chief was Ralph Bellamy, and I was Eddie Murphy rolling around on a furniture dolly, pretending to have no legs and begging for money. I wondered if I was being “punk’d” (to use a phrase that not only dates me but makes it seem like I used to watch MTV’s Punk’d hosted by Ashton Kutcher, which I did, but still).

“The lousy bastards,” I recall muttering away from the phone. (Note: I almost certainly didn’t mutter “The lousy bastards” away from the phone.)

The moment he said “Esquire” I remembered that one of the many questions he’d asked me earlier in the conversation was, “If you could work at any magazine at Hearst, which magazine would it be?” (This is a typical recruiter question—forces you to either qualify or disqualify yourself.) I’d said, “Esquire,” in the same way Oliver Twist says, “Please, sir, I want some more.”

And so, armed with deep skepticism, I responded like . . . an excitable schoolboy.

“Really?!”

“Could you come to New York next Monday?” he said.

Esquire had been my favorite magazine for years. It was the magazine I modeled my own magazine after. Working there was a dream I’d never allowed myself to have. “This will end in utter failure,” I thought. “If I don’t get rejected after the editor in chief reads my résumé and sees that I went to a school with a name involving a cardinal direction, I will screw up this interview like no one has ever screwed up an interview. I will spill coffee on the editor in chief’s desk. I will forget to wear socks.” (Years later, I would find out that socklessness is considered a virtue by people in fashion.) “I will improbably mispronounce ‘Esquire’ as ‘es-QUIRE,’ as if I am Javier Bardem. I will inexplicably urinate on a plant.

“Even worse, I will forget everybody’s name, talk too fast, and screw up the handshakes.”

This kind of auto-psych-out is routine for me. I never feel “up to the task.” I feel “at war with the task.” I feel like the task is taunting me, reminding me that I grew up in a neighborhood in Dallas supposedly on the wrong side of the tracks; that I played lot of ragtag neighborhood games when I was a kid but never competed in an organized way; that I made terrible grades in school; that every day of my seventh-grade year I was literally kicked in the ass by a kid whose name I didn’t know and who never said a word to me; that my mom—who raised me as a single mom from the time I was three months old—took me out of what she considered a dangerous public school where a mute kid could daily kick her son’s ass unchecked and put me into a tiny evangelical private school simply because it was near our home; that my teachers there constantly “prayed for me” because I didn’t seem to be “accepting Jesus as my personal Lord and Savior”; that my graduating class had only eight people in it—eight!; that, despite my terrible grades, I was the salutatorian in that class of eight people—salutatorian!—but that I was only “acting” salutatorian because the kid who earned the spot was kicked out of school for behavior reasons right before graduation; that I went to the University of North Texas, not the University of Texas; that I worked at an in-flight magazine, not a newsstand magazine; that even despite my automatically privileged status as a random white guy, I’ve always felt like I was in the second or third tier and never the first. Ever. The recruiter, who represented the big stage, was talking to someone who’d never been on the big stage. I was never part of the main thing. I was always part of the other thing. Challenges like going to New York that Monday only highlighted my class B status.

(Fortunately for my career, when I am faced with a challenge, my reaction is fight, not flight.)

Despite the near certainty of those failures of comportment that surely awaited me—at a magazine that is an authority on comportment!—I gave him the only answer I could possibly give, the answer we all must give when opportunity calls us up and seems to taunt us by asking if we are bold enough to become more successful: “You shittin’ me?”

I eventually said something that meant yes, because a week later, I was leaning against the wall of Merchants’ Gate at the southwest corner of Central Park, across from Columbus Circle, a block away from the magazine’s offices, on a beautiful Monday morning in May, reviewing ten pages of responses to possible interview questions that I’d handwritten the night before, and feeling like I was a character in a lesser Nora Ephron movie.

I was very early. I was wearing my nicest shoes. I was wearing a tie. I was—

Wait a minute. I wasn’t wearing a suit jacket.

I should’ve been wearing a jacket.

Why wasn’t I wearing a jacket?

2

Should You Keep Reading This Book?

Circle each answer that applies, and add up the points to find out if you should stick with this.

Which word best describes how you read the first two chapters?

Devoured (5)

Skimmed (4)

Used as makeshift umbrella (2)

When you walk into a room, which type of gait are you most likely to exhibit?

Swagger (0)

Mosey (3)

A slink-type deal (5)

Is your alma mater part of the Ivy League?

Yes (–8)

No (2)

If your alma mater is part of the Ivy League, are its buildings actually covered in ivy?

Yes (–15)

No (0)

Are you aware of any of the following? Circle all that apply.

What color your parachute is (–4)

Where your cheese might be (–4)

Whether you’re leaning in or leaning out (–4)

Which of the following have you accidentally said in a professional situation instead of saying “Thank you” because of anxiety?

“You’re welcome.” (2)

“Thank welcome.” (4)

“You’re you.” (6)

Which of the following do you regularly do at work?

Chew your fingernails (3)

Weep (4)

Weep while chewing your fingernails (10)

You’re hired!

“I knew it!” (–7)

“Oh shit.” (5)

Quick: Draw a boat that represents you on your professional journey.

Which kind of boat is that up there?

Yacht (0)

Cruise ship (–10)

Dinghy (4)

One of those banana things they got in the Caribbean (7)

Draw a boat? How is this helping me? (-30)

Which is the most useful professional tool?

Ambition (–5)

Competitiveness (–6)

Eye contact (4)

Staple remover (0)

Backup staple remover (0)

Which best describes your mouth right now?

Smile (0)

Robotic grin (–3)

Frown (10)

Indifferent simper (5)