How Far Can You “Lean In” if You’re Not Pretty?

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There’s been a lot of talk lately about the so-called “lean in” concept, and the pressures put on young women in our culture to be and do it all, whatever “all” is, and work-life balance and all that. In the midst of which, as the mother of college-aged daughters, I often find myself wondering: would female executives like Facebook’s Sheryl Sandberg (author of the “Lean In” concept) or Yahoo!’s Marissa Mayer be where they are today if they weren’t so darned attractive? And what do I tell my daughters about the answer to that question?

Of course, female attractiveness is unrelated to merit or ability. That’s the feminist party line—and yet we all know that attractiveness matters. It matters whether one is male or female, but if you are female it matters a whole hell of a lot more. And yet, it’s a complicated subject.

Back when Gloria Steinem went undercover as a Playboy Bunny, the rules by which women’s bodies were objectified in our culture were simple: men looked, and men set the rules. Today, women largely determine whether, and in what way, we will allow ourselves to be objectified, whether it is on a “Girls Gone Wild” video or a shareholders’ meeting; the difference is, we call it something else, like “owning our sexuality”—and men are not supposed to notice, unless they are talking about their wives or girlfriends.

Remember when President Obama stepped in it for calling California Attorney General Kamala Harris “the best-looking attorney general in the country”—which she probably is, by the way—and Obama immediately got smacked with the label of “sexist”? His crime wasn’t noticing an attractive woman; his faux pas was in saying he noticed.

We have entered a strange new sexual territory in which Sheryl Sandberg can wear a slinky red dress and glam it up in front of some computer infrastructure, but to state the obvious—that she is totally hot—is considered déclassé. In fact, the more beautiful a woman is, the less her looks are supposed to matter.

But they do. They may not matter in the way such things used to—nobody would suspect Sandberg of sleeping her way to the top at Facebook—but they matter. According to my own exacting scientific survey, which consisted of Googling the names I found in a couple of Fortune 500 “Top 20 CEOs” lists and looking at a lot of pictures, there’s practically no such thing as an unattractive female CEO. (I say “practically” because I did find one woman who either is admirably immune to our culture’s superficial obsession with looks, or who needs to find a new stylist immediatemente. Call me, sweetie.)

Of the top female executives, six easily qualified for the “wow” factor, and you could argue for a seventh, based on the fact that in her younger pictures she simply glows with loveliness. We’re talking way-above-average looks here, of the kind that could get a person work in the movies. Life insurance executive Deanna Mulligan bears more than a passing resemblance to a young Charlotte Rampling, who was ravishing in her day; pharmaceutical executive Heather Bresch could find work as a film double for actress Nia Vardalos.

Now for the guys. I am a sucker for the powerful-but-graying older man type, so I would have expected that plenty of titans of American industry would spike my pulse at least a little. Yet there were only two I could find who even came close —James Dimon of J.P. Morgan and Rex Tillerson of Exxon — (and I’m not sure about the latter; it may be simply that I’ve always thought the name “Rex” was kind of sexy). A lot of them the male execs I found, as with the female CEO’s list, fell into the “okay” category—neither stunning nor unattractive. Then there were my impressions of the rest of the guys, as recorded in my notes:

“Methodist church deacon, circa 1955”

“Sam Donaldson’s older brother”

“Oh my lord.”

“Howdy, Grandpaw!”

Interestingly, the only obviously overweight person was a man. Even in our weight-obsessed culture, guys can still occasionally get away with being fat. Women executives simply cannot. Men who run companies get away with looking pretty darn average; to be considered “average,” a woman still has to rely on hair dye, expertly applied make-up and at least one layer of Spanx. And let’s not forget plastic surgery.

The flip side of stating the obvious—that women’s looks matter more—is its corollary: the penalty for unattractiveness is much, much harsher than it used to be. A century ago, when most career doors were closed to women, pervasive gender discrimination was a kind of shield against the harsh judgments of the bathroom mirror, but that’s no longer true. Some things, like bad skin, you can fudge; some things, like extra pounds, you cannot. Stunning beauty is, by itself, no longer a requirement for female success in a narrow range of fields (actress, opera singer, society hostess). But 99.9 percent of the time, unattractiveness is, by itself, an absolute disqualifier for high visibility in almost any career, if you’re a woman.

I wish I could tell my daughters something different, and reassure them that talent and character and hard work are all that really matter in life. I wish I could tell my daughters—who are both lovely, by the way—that what really mattered was their own pleasure in their bodies, and their health and well-being, and to disregard all these superficial standards of beauty because they just don’t matter. But if I did, I’d be lying.

You can find guest contributor Tracy Thompson at her website,, and at her blog, The Blockhead Chronicles. Her most recent book is The New Mind of the South.

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How far can you Lean In if You ARE Pretty? Aliza Worthington looks at the flip side of this predicament.

If you’re interested in purchasing Lean In or Tracy Thompson’s book, The New Mind of the South, please consider purchasing it here (see the links below). The Broad Side will receive a portion of the cost, which we’ll use to help pay our fabulous writers and keep our unique content coming!

  • I find myself curious – while I won’t doubt attractiveness to a certain extend can bolster a woman’s career path, yet can also be a detriment if she’s “too” attractive at higher levels – how much of the fact so many CEO’s are attractive women isn’t also simply attributable to the fact as they’ve risen through the ranks they have the income for the best skin care, medicine, and health – maximizing their natural gifts?

  • It is definitely possible to be too pretty, I’ll agree.But don’t you think the things you mention would apply equally to men as well as women (since guys, I’m told, now go in for facials and both genders hit the gym). This argument actually also bolsters my point, in that “maximizing their natural gifts” is going to take a whole lot more for women, in the form of Botox, cosmetics, hair styling and wardrobe, than it would for men–at least in terms of time, if not money.

  • Lindsay

    great post. It’s a complex and tough point you raise. yet another important, yet unspoken layer/barrier to put on women.

  • Tina

    This is a really important point, and a well-written one. In the realms of age and obesity, there are many studies showing that women are disproportionately discriminated against in the workplace. Essentially, you can be an overweight graying man and be fine. An overweight graying woman? Not so much. Good article.

  • JMD

    Here’s what happens in a workplace:

    The smart but unattractive woman can pull off some Herculean feats, but she’ll keep seeing promotions go to more attractive women. She’ll query and be told that she’s a crucial part of “the team” but just isn’t ready for a promotion yet. She’ll re-double her efforts. She’ll come up with some brilliant plans and execute some remarkable strategies, believing that there’s no way they can deny her a promotion now.

    Then one day Ms. Unattractive will be sitting in her cubicle and the boss will bring another woman around. He’ll introduce her as the new Director of the X Department. He hired her from the outside. Ms. Unattractive will Google her and be dumbfounded to learn that Ms. Beautiful has little relevant experience.

    She’ll go to her boss and ask why she wasn’t considered for the position after 7 years as Manager. He’ll make up excuses and even tell her things she was never told before, such as “the team” isn’t comfortable with her; she’s too “intense”; she’s not “quite ready.” But, he’ll add, we really need you, there’s no one better at your job — so how about a 7% raise and oh, by the way, can you train Ms. Beautiful?

    Ms. Unattractive will begin to suspect that her looks are the issue, but when she goes to people for support — including friends — they’ll deny it. They’ll just tell her she’s got to be more creative, try harder, work smarter, show how much she really wants it….although this is exactly what she’s been doing for seven years.

    She’ll move on to another job, and at some point she’ll realize that Manager is as far as she’s going to go in the corporate world. Her friends accuse her of “giving up”, but that’s not quite true. She’s fought harder and longer than most of her attractive peers ever will, only to be told that she — obviously — wasn’t creative enough, smart enough, or savvy enough. Yet if there was an objective test on these qualities, she’d beat out all the attractive women who were promoted above her.

  • I agree looks matter, particularly for women who want to climb the corporate ranks. It’s also been well documented that we discriminate against people who are very (perhaps even mildly) overweight.

    However, you lost credibility about your concern for what these type of societal thinking would do to your daughter, when you made the comment about the one woman CEO who was not attractive to “find a new stylist immediatemente. Call me, sweetie.”

    Really? “Call me sweetie” so you can style her and make her attractive? The call me sweetie was demeaning enough but that you wanted to make her more attractive means our societal culture about woman has infected you too.

    • Josie

      “Really? “Call me sweetie” so you can style her and make her attractive? The call me sweetie was demeaning enough but that you wanted to make her more attractive means our societal culture about woman has infected you too.”

      Well, whether it was intentional to demonstrate this or not… that is sort of the point.
      It is all utterly pervasive. Pretty much no one is immune.

      I have my doubts that you are.

      We all want to think that issues like this can be sorted in black and white. Like so many other things it is just not so.

  • Oops. I am Southern born and we are pretty free with the “sweeties” and the “hons” and the two-name names, which is why to my Atlanta friends I am TracyLynnJeanMarieLouise. In that context, “sweetie” is not demeaning; it’s just how we talk. But I agree that’s not going to come across on the page, so: my apologies.

    Also, if anybody saw what I look like 90 percent of the time as I sit in front of my computer, they would know I would welcome some company in the Remedial Cosmetics Class.

    • Even without the sweetie, your point was still that this woman better start making herself look more attractive immediately (and that you have superior skills in this department, of course.) This is in spite of the fact that she is already advanced in her field. That’s incredibly condescending, and reeks of “bless her heart,” another southern phrase that is used to sound nicer than it means.

      I just find it frustrating that in an article where you are searching for honest, fair answers for your daughters about looks and climbing the corporate ladder, you seem oblivious to your own behavior. It seems to me you should tell your daughters that many people judge women unfairly for how they look, and their mommy is one of them.

  • My sister lost a lot of weight (A LOT) and was only then was promoted. This is no laughing matter.

  • I found this particularly interesting as I recently did an episode of my podcast on just this topic. Women undoubtedly have to keep up their looks to a greater extent than men do (although one of my guests would argue we just do it differently). But on the topic of female CEOs, I have met at least one successful entrepreneur – so admittedly not leading a Fortune 500 company – who was far from slim, but very successful. She dressed well and was well groomed, of course. But also, what about Hillary Clinton? Not a CEO but a powerful leader who isn’t traditionally beautiful, but has had to pay a lot of attention to her appearance. She comes up quite a bit in my show on this. Here’s the link in case you’re interested:

  • At first, Hillary Clinton looks like the exception that proves the rule. She isn’t beautiful; there have been occasions when she’s not always been perfectly groomed (though I would argue that flying ten zillion miles across 6 time zones in service to her country should render her immune from criticism on this score).Yet she is powerful. More to the point here, however, she has also taken just an unbelievable amount of shit –a perfect storm of shit–over the years about her looks. I mean, Chris Christy gets some fat jokes, but that’s affectionate teasing compared to the treatment Hillary’s gotten. So if anything, I would argue that she is just one more example of the argument I’m making.

    • Sadly, Hillary has taken so much grief for her appearance at so many different points of her life — Coke-bottle glasses, unkempt hair, outdated headbands, Cleavage-gate, pantsuits. I could go on. But I agree with Tracy — Hillary is the perfect example of others trying to push her back because of her appearance.

      • This was a point I have often made how looks add to brains every time and so does style. Have you seen “What not to Wear?” On the male side we do have a standard. I have referred to it as “tall man syndrome” long before another writer researched the phenom. Height in men is often the standard by which they are judged, while attractiveness in women seems to be a KPI. As far as Hillary Clinton, I beg to differ. While she has taken some heat by national press over the years, she is not an “unattractive woman.” She was certainly of a certain weight as a younger woman and looks pretty good even today, even after thousands of air miles and dealing with crises across the globe. I am sure she and Bill were thought of as a hot campus couple in their day.

  • Jen

    This is an important point that needs to be raised more and your quote about Sheryl Sandberg’s sexiness but the obvious declasse of stating so was so RIGHT ON.

    What about how women may or may not use their sexiness in the workplace, either knowingly or unknowingly? They do, and there is absolutely nothing wrong with that. And I don’t mean sleeping with the boss sexiness — I mean sexual energy = confidence. This is just flat out fact. When you feel pretty or sexy (whether you are or not.), you are more confident and secure. You feel more powerful and then act more powerful. This is a tool women can and should use in their workplace, and should not have to be afraid to do so because men don’t get the hint; because their male colleagues misinterpret their confidence as come ons.

  • This article takes an interesting perspective – shining a light on something many of us have known for years. While I am a believer that competence and confidence are extraordinary compensation boosters, the realities of pay discrimination in women’s lives persist, worsened by broader cultural issues of “looks” discrimination that range from weight to height to hair color and more.

    That doesn’t mean we, as women, yield the good fight. But nor can we deny that the human tendency to attribute competence and character traits based on appearance is alive and well – and by the time we reach an age / stage where we’ve learned to “compensate” in order to be compensated, we’ve nonetheless lost years of cumulative benefits, not the least of which are pensionable / retirement earnings. .

  • Sara

    Interesting. I recently participated in programs with major MDs – at least one woman in every group of men – and I certainly would not use ‘attractive’ as a way to describe most of them. Tired-looking is the double-barreled word which comes to mind.

  • M

    This is not a female thing.This is a human thing. Most male CEOs are above average height. I don’t think it is smart to reduce this down to just facial looks and call it a female problem.

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