by Megan Hustad
There’s been some theorizing about why VIPs flaunt their less than glitzy beginnings. In his studies on high-status people (and how they finagled their way into people’s hearts), Edward E. Jones claimed that self-deprecation made them more approachable. Being at the top of the heap, they needed to command respect and authority, but they also needed to be seen as regular folks in order to enjoy unmolested success. If they were too aloof, too distant, they were more likely to be attacked by disgruntled employees—or by anyone they outranked. But if they made self-denigrating remarks now and then, or stressed how, at the core, they were painfully plain people, they would be less vulnerable.42 They would also, Jones believed, be associating themselves with characteristics Americans prized, like modesty and honesty. Most important was the simple fact that they delivered these humble beginnings stories from the very top of their professions. That provided the punch line: they’d scrambled up from nowhere special, sometimes from somewhere very crummy indeed, and so were clearly made of the right stuff. It made their success even greater. (Getting a book deal, so you can explain all this at length, never hurts.)
Self-deprecation is obviously trickier when you’re low on the totem pole—you have no status, and maybe for good reason. You can’t exercise your humility too much because there’s no roaring success to serve as juxtaposition (and make the larger point of your brilliance for you). Here’s one example of how an attempt at self-deprecation can go terribly wrong: During an informal job interview at a small retail-design firm, I was asked about my first real out-of-college job, which, it so happens, was assistant manager of the Fifty-seventh Street Rizzoli Bookstore in New York. My first day on the job—I was twenty-two—I was given a set of keys. Three days a week, I opened the store—switched on the lights, booted up the computers, opened the basement safe, counted the cash and put the cash drawers in the cash registers, and made sure all three floors of the store and everyone on them were ready for business. Then I ran around for eight hours. Three nights a week I closed the store—tallied the day’s receipts, counted the cash, closed the safe, shut off the lights, and locked the doors behind me.
Ten years later, this is how I described that job to my interviewer: “Pretty much everything. I ordered the toilet paper.” I realized my mistake when he, sitting across the cafe table, repeated this phrase back to me: “You ordered the toilet paper.” He said it flatly, declaratively, without affect, as if he were accusing me of an unhealthy fixation on bathroom humor. I was counting on the chance to expand, to explain how in fact the job was much more than that, but he quickly changed the subject.
Clearly my attempt at self-deprecation fell flat. (I’d just come off five years in a corporate setting, and didn’t want to appear to be above retail work. But he evidently thought my qualifications plenty humble.) There’s some comfort in knowing this mistake is a fairly common one: people will trumpet their humility and unimpressiveness to convey that they’re really down-to-earth when, in fact, everyone thinks of them as quite earth-bound already. “There was this girl in our office who boasted about the dismal small town where she went to high school,” said Jill. “You know, one of those ‘Population: 817’ towns, as if she wanted to say, ‘Hey, look at me now!’ but the thing is, she was a mess. So for me it became more like, oh, that explains why you saunter in at 10:30 with your hair unbrushed.”43
But a humble beginning is too great a potential asset to waste, regardless of your position on the totem pole. In Secrets of a Corporate Headhunter; from 1980, the author and executive recruiter John Wareham claimed that a little bad start went a long way. He said that he always looked for “a slight abrasiveness” in the people he recommended for million-dollar leadership positions. These men and women needed to have a kernel of resentment somewhere inside—like “the grit an oyster needs to produce a pearl, or the rich manure that feeds a luxuriant rose”—in order to be truly effective. Coupled with complementary character traits like tenacity, an inferiority complex could be very useful in an executive (as it meant he would always be “proving something to the demons in his head”).
Wareham’s book wasn’t alone among books that ushered in the business-mad 1980s in highlighting the appeal of a less than spectacular past—as long as resentment didn’t take over. In his book The Over-Achievers, the former Helena Rubinstein executive Peter Engel ventured that the key component in an executive mindset was not being spectacularly smart (excess intelligence being “a very sly asset” in his opinion), or in any way pedigreed, but that you were above all “emotionally glamorous.” Every important businessman, he claimed, knew how to turn liabilities into assets, and this required complete objectivity, even when considering personal matters. Being emotionally glamorous, then, meant being able to assess one’s own strengths and weaknesses as critically and dispassionately as if they were someone else’s. Overachievers knew better than anyone else what was wrong with them—and they weren’t afraid to have their faults, flaws, or shortcomings aired.44
Figuring out where the chinks in your personal armor were could be difficult, and so it was important to undergo regular and ruthless self-inventories. “Don’t kid yourself,” advised Crawley A. Parris, author of Mastering Executive Arts and Skills. “Essential to successful self-development is the ability to see yourself as you really are.” Easier said than done, of course, which is why so much of the success canon stresses listening over talking—if you weren’t really listening and observing other people “aggressively” (as Mark McCormack advocated in his 1984 What They Don’t Teach You at Harvard Business School), you wouldn’t be aware of how other people were reacting to you, and if you weren’t aware of how other people were reacting to you, you’d be much more prone to self-delusion. Therefore much of the work of becoming emotionally glamorous took place off the clock, at home alone, while you stared into the bathroom mirror and pondered the events of the day.
In practice, on the clock, demonstrating emotional glamour meant mastering a jaunty, “Well, that sure blew, but what do I care about it now? Life is good!” way of describing the past. All humble beginnings stories needed to sound matter-of-fact, to minimize real suffering and conveniently skip over any emotional fallout. Some people do this very well. They recall stupid incidents from their past and deliver them with a laugh.
This is how my colleague Jenny describes her first job out of college. She wasn’t keen on going back home to Wisconsin after graduating from Cornell; instead, she wanted to explore more of the East Coast, and eventually found a job at Harvard’s career counseling office. She found it somewhat awkward dispensing advice on how to get jobs, given that this was her very first one. But it was good work, and she calculated that being able to add Harvard to her resume couldn’t hurt either. Still, the students Jenny was asked to counsel were only two years younger, and she always felt a little self-conscious about that. She decided to use her own inexperience as a plus, a way to relate to them better. “I just graduated from Cornell,” she’d say. Then, as she tells it now, she often received the following response: “Oh, but that’s a good school!” These students were taking her “just” to mean not “recently,” but “only”—that is, they were assuming she probably felt a little inferior. Jenny, who now works in fundraising, clearly enjoys telling this story. Every time she delves into it (I’ve heard it three times now), her eyes—big and brown—sparkle.45
As Parris insisted in Mastering Executive Arts and Skills, griping was a definite no-no for any middle-management guy who aspired to higher levels. Griping had a decidedly “unexecutive look” to it. One also needed to avoid any sort of hangdog, woe-is-me posture. This too is critical to the effective self-deprecating remark: it has to focus, if not directly then with a sideways glance and a wink, people’s attention on a slate of positive, ready-for-prime-time qualities. And this is where most people go wrong. In his work on ingratiation, Edward E. Jones floated the idea that a lot of low-status people tend to deprecate important qualities and play up insignificant ones. In other w
ords, they think they are testifying to their grit, when in fact they are making themselves look like the guy who’s going to careen off the edge in a haze of self-destructive tendencies and unresolved seventeen-year-old rage. Or they want to show off a sense of humor, when their basic integrity hasn’t yet been established. This is a costly mistake.
The wrong type of self-deprecation always has an element of self-mortification to it—and it generally follows the same pattern. Coworker drapes herself over the top of your cubicle, leans in, rests her head on her hand, and sleepily drawls out a story of stupidly agreeing to that one last drink, or of getting lost and arriving late and stepping in a huge puddle, of losing a wallet in the back of a cab, or of making a mistake that elicited a spectacularly scathing fax from a major client. She tells you how her college Italian professor had requested that she please drop the class because she was clearly never going to learn, or how her roommate blamed her for the new dead-animal smell in their fifth-floor walkup apartment.
Caroline—who admits this now with admirable candor— prided herself on telling these stories, which nearly always got a laugh. Then she noticed some other reactions, reactions like, “You poor thing. That would only happen to you.” Caroline was tempted to ignore the first person who resisted her charms because this other woman generally limited her interoffice chitchat to things like her last visit to London, and how funny it was that she went to the British Museum looking for the Rosetta stone and walked right past it—twice—before she finally asked a security guard and he informed her—stupid, right?—that she was standing only six feet away from it. Or how that novel she edited, the one that became such a sleeper hit, well, the fact that she even discovered its author was a fluke. Caroline was aware that she sounded very different from her colleague, whose style —which she found weirdly brittle and hollow—was one she did not want for herself (“I think not admitting to weakness is itself a sign of weakness”). Then one morning a more soft-spoken colleague, a friend, left a long pause after one of her puddle stories before saying: “You always have stories like this.”
Which suggests that in addition to boring people, her stab at emotional glamour was not making the correct larger point. She was always the unwitting victim of circumstance; that is, when she wasn’t laying down and rolling around in it. While growing up in some backwater town or receiving an inferior education can be overcome, the same can’t be said for a bad work ethic, chronic lateness, or sloppiness—so if your audience already has misgivings about your ability to compete, best not to encourage those doubts. Caroline was also making the rookie mistake of volunteering information no one needed to know. As the rundown in The Over-Achievers suggests, the smart self-deprecator would have figured out what flaws people had already picked up on, or what exactly about her habits, looks, or resume any given person might find tacky or objectionable. And then she’d bring these things up herself, essentially saying out loud what she guessed her audience was thinking already.
This preemptive self-deprecation works, I believe, because most of us—perversely, sometimes meanly—enjoy locating the chinks in someone else’s armor. If you can point out where your own chinks are first, you take away someone else’s fun—and disrupt whatever play for dominance he or she might be attempting. It’s undoubtedly why a writer I know often says, “Oh, I went to a stupid school…” before going on to say that he attended the University of Michigan.46 An aspiring Hollywood player who has never sold a screenplay but who regularly gets enthusiastic commendations from producers and agents says he is “the Dan Marino of Screenwriters” (and then relates how a studio exec once called him that to his face, only he didn’t know who Dan Marino was, and then the studio exec had to explain that Dan Marino is widely considered the greatest quarterback who never won a Super Bowl). This preemptive self-deprecation disposition is on every page of Bridget Jones’s Diary. With Ms. Jones admitting that she “smoke[d] self into disgusted frenzy” on a regular basis, Helen Fielding has her character flagellate herself before anyone else does, making her less pathetic, more endearing.46
It’s a more nuanced strategy than it seems at first hearing. “The Million-dollar Executive”—Wareham’s term for the new high-rolling head honcho—was very aware that he might be called on his bluff someday (that alone was reason for trotting out that humble beginning story). So he had to develop something close to clairvoyance. Which is to say that F. Scott Fitzgerald made a strange choice when he had Jay Gatsby going around telling people he was educated at Oxford, and boasting of having spent subsequent years “like a young rajah in all the capitals of Europe—Paris, Venice, Rome—collecting jewels.” Surely Gatsby would have already figured out it was better to let folks know he’d brushed the dust of North Dakota off his jacket before coming to Long Island.
The successful self-deprecating remark also has a particular inflection—it ends with a falling intonation (not the “uptalk” that suggests a question, or implies you have no idea what you’re talking about). It’s delivered snappily, and sometimes veers into the cinematic. Wareham’s own version reads like the opening scene of a black-and-white movie: “sixteen years ago, clutching the proceeds of a $1,000 IOU scrawled upon the back of an envelope, I took my first office and hung my first shingle outside a 200-square-foot walk-up office suite. It boasted rat holes and the solid vista of a decaying brick wall.” The most perfect one-line example I’ve heard was delivered by a D.C. congressional aide, who summed up her background by stating simply—and factually—that her high school’s mascot was a cotton-picker. The same rule of delivery applies to mistakes or professional miscalculations. The screenwriter William Goldman claims that one of the best pieces of film dialogue ever, the one that makes the lead character come across as personable, fallible, honest, tough, and generally sympathetic all at the same time, is when Casablanca’s Rick, after being asked what had brought him to Casablanca, responds, “The waters.” What waters? his questioner wants to know—Casablanca was in the desert. Says Rick: “I was misinformed.”
In order to demonstrate how high-status people emphasize their positive character traits in important areas, it’s worth returning to Helen Gurley Brown. One version of her many humble beginnings stories goes something like this: at eighteen—“flatchested, pale, acne-skinned, terrified”—she gets her first job, sorting mail for Mr. Wilson, the emcee of a radio breakfast show called Rise and Shine. A big part of his show was announcing listeners’ birthdays, anniversaries, and so on, and it was Helen’s job to distill the pertinent information from listener letters and type it up on index cards. Wilson would take these cards into the studio and pretend to read, pausing and hemming as if he were perusing the actual letters. “Well, well!… Little Deborah Jean Dallyrumple over in Gardena is having a fourth birthday! Let’s see. It says here if Deborah Jean will go look out in the garage in Daddy’s tool chest, she’ll find something…” Gurley Brown claims she wasn’t good at this, often mixing up names and locations, and that she botched a lot of Happy Birthdays for boys and girls across Southern California.
Now, whether she was really terrible at this job is beside the point. The story somehow manages to suggest that she was a dedicated worker (job at eighteen), has a good memory (lots of details), is honest almost to a fault, that she tried but failed sometimes, and maybe only failed because she knew how inconsequential her job was (is four-year-old Deborah Jean really going to remember, later on, that the radio announcer man directed her to the wrong part of the house?). And yet her post was not so inconsequential that her gaffes didn’t have far-reaching effect (it’s possible she made Deborah Jean, and hundreds like her, cry).
The successful self-deprecator always places herself not just at the center of her narratives, but as the character performing the pivotal action. Not only is she no victim of circumstance, but things happen because of her. She sets things in motion. This is perhaps the big-money, bedrock reason for self-deprecation’s effectiveness. One of the stories told about Jack Welch is of a GE managem
ent training class held sometime in the mid-1980s. It’s late in the evening, and in the conference room are ten new hires, mostly young guys, who’ve been at it all day. At the end of the table is a flip chart, on which are scribbled two propositions for debate: (1) Jack Welch is an asshole, and (2) Jack Welch is the greatest CEO GE has ever had. This exercise was done with Welch’s full blessing—it may even have been his idea. It struck me as particularly shrewd, for several reasons. Holding yourself up for criticism when you’re on the top of the heap, even instructing your minions to do it, is smart. But Welch also sketched out the very terms by which they could do it. No dabbling in gray areas for him, none of the shadowy regions inhabited by more lackluster personas. Either Welch was a jerk or he was the best man that company had ever seen. (Or both. The categories aren’t mutually exclusive.) But any way you sliced it, he was an archetype, one for the ages.
