Whenever anyone tells you to “celebrate your femininity,” you should be very suspicious. Certainly there’s nothing wrong with femininity (or celebrating), but generally anyone who gives you this festive directive is passive-aggressively indicating that your particular brand of femininity is just all wrong, and that instead you should 1) wear a dress, you dirty rugby player, 2) get your clitoris sensually rubbed in a group workshop for 3) wear a denim jumper and stop using contraception.

So, no to that. But, one day in Barnes and Noble I spotted a book entitled How to Live Like a Lady. I flipped open to a random page that must have been the most meritorious page in the book (for instance, page 83 explains “how to eat a whole fish”), because I actually purchased this sad little manual, which later when on to inform me that:

  • T-shirt bras look really smooth under a t-shirt!
  • “Floppy breasts barely held in by a saggy, too large bra” are a faux pas.
  • The best way to sit in a skirt (and give yourself deep-vein thrombosis!) is to “cross your legs at the knee then tuck your front foot behind your back ankle” to make sure no one sees your dirty whore parts!
  • Only sit in uncomfortable chairs, since it’s hard to keep your back straight and your legs together in a cozy armchair.
  • When you enter a room, be sure to hold back and let your companion choose his or her seat first. (Hmmn, when should you do this? When you’re with men, women, your boss, your employees? A little weird, right?)

Oh, also make sure that any jokes you tell are self-deprecating (“there’s nothing worse than being perceived as bitchy or malicious”). I guess there will never be a lady Jon Stewart, as telling jokes at Gaddafi or John Boehner’s expense would be unladylike.

Clearly, this book is stupid, and the few useful things it had to say were not at all gender-specific. It’s always rude to ask people what they paid for their handbags, and if you eat an olive at a dinner party and no dish is provided for pits, you should spit the pit into your napkin, regardless of the configuration of your sex organs.

So, this got me thinking. It seems that I can divide all of the lady advice I’ve ever heard into three categories: 1) Etiquette advice for everyone, 2) Fashion and beauty advice that belongs in a fashion and beauty publication, and 3) Really awful advice that will kill your career.

Rather than running your career and life like a “lady,” I think you should run it like a gentlewoman. (See Bullish: How to Travel Like a Gentlewoman.)

What’s the difference? Well, some of the outward behaviors are the same, but it always seems to be that “being a lady” involves some component of acting adorably appropriate and then waiting for a pat on the head (or, if you are an old lady, a pat on the head from Jesus).

The word “gentlewoman” has meant many things (including “lady”) over the course of its history, but today, I think its meaning is distinct. A gentlewoman is generous, genuine, comfortable in a diverse array of social situations and foreign cultures, dresses appropriately, stands up straight, tips well, knows to take a Japanese person’s business card with both hands, and can pronounce “Hefeweizen” … but hardly considers all of these things a full-time fucking job. These are the basic requirements; they cannot occupy more than 5% of your mental space if you’re going to get anything at all done.

Here is a Venn Diagram regarding the differences between a lady and a gentlewoman. I made this with colored pens and also by using a coffee can to draw circles on paper! (See Bullish: Pre-Internet Productivity Tips for the Young and Sprightly.)

So, here are a few tips on running your career like a gentlewoman.

A gentlewoman is generous, but not in a pathetic way

Oh, you have the last dinner roll! No, really, you must. I know it’s my birthday, but deep inside I feel both superior and martyred when I make small, pointless sacrifices for others!

So, don’t be fucking pathetic. If you take the last roll in the bread basket, flag down the waiter and get some more goddamn bread. Pointless little guilt-inducing sacrifices are the refuge of deeply disempowered women – grandmothers who could have run companies or built aqueducts or performed surgery, and instead were forced to iron things and always eat the most smushed piece of cake.

A gentlewoman is kind and generous to anyone who isn’t a threat or a serious competitor. A pep talk, interested question, or moment of mentoring in an elevator doesn’t cost you anything. If you have maternal instincts, you can use them in business. Plenty of men came up in their careers because someone treated them “like a son.”

And then: anyone who really is a serious competitor should be treated with civility, whilst you are coolly gathering information.

A gentlewoman is comfortable with money

A gentlewoman should tip well, of course. And furthermore, a gentlewoman does not wait for other people to pay for things. A gentlewoman does not halfheartedly open her purse and then look confused, waiting for someone else to jump in. Certainly sometimes other people will pay for you, in a variety of perfectly acceptable circumstances. But if you reach the point of pulling out your wallet, say something in a normal voice. For instance, “Should we split this one?”, or “Here’s forty, that should do it.” Please don’t embarrass all women with equivocal little-girl money bullshit.

But back to careers: It’s hard to imagine a “ladylike” person effectively negotiating for a raise. Here’s something interesting: I negotiated an agreement with a company I worked for, and felt that I had been firm and assertive, and had done a good job in the meeting. Nearly a year later, the same boss referred back to that meeting and said he was glad I’d been so “collegial” and “not adversarial.” My gauge for what constitutes firmness was actually a bit off – much like women who refuse to lift weights less they “turn into bodybuilders” (umm…), I actually could probably become even more direct and “assertive” before others even considered it that.

A gentlewoman is not sexist, even though she could probably do some damage

This April, New York Magazine ran an article about Lynn Tilton, who claims to be a self-made billionaire and the owner of more businesses than any woman in America. This may or may not be true – Forbes, in a much more technical article, has uncovered some shady-sounding financial activities (“But what does it all add up to? There are billions of investor dollars at stake–and Tilton’s outstanding CLOs have been downgraded.”)

But both articles report a lot of this: “Outside her suite are handcuffs, a whip and a cowboy hat–emblematic, she says, of her kicking companies into shape.” She once grabbed Tony Blair’s ass; about this, she comments, “With one hand I stroke; with the other hand I smack!” A male employee adjusts her drooping boot (WTF?), and she comments, “That’s what I like – a man on his knees.”

Now, in her defense, some of her behavior is in response to deeply sexist, aggressive, powerful peers, in which case we might just conclude that some business environments are very crude places. Tilton is also very entertaining. Oh, but then there’s the part where she’s being sued by an employee for wrongful termination. New York interviewed a number of her male employees:

“It’s a form of control and humiliation,” says another employee, adding that the experience of working for Tilton was so emasculating that it took him months after leaving the firm to have sex again. This employee also says that Tilton perceives all of her male employees as being in love with her. Which is perhaps the reason that, holding court in a conference room during her 50th-­birthday party, Tilton offered her male employees a choice: They could take a Jell-O shot off her stomach or lick whipped cream off her breasts. “The crazy part was, she saw it as morale building,” says one person present. “People were hiding in the bathroom.”

Holy fucking hell, Batman.

Of course it is possible to be “all woman” in your career, and if you run your own company, you can probably wear whatever you want, including what Julia Roberts wore in Pretty Woman. However, obviously, you cannot demand that your employees lick whipped cream off your boobs. This is what Craigslist is for: finding a stranger who will do that for free. And I don’t think it’s out of the realm of gentlewomanly possibility that one could hire a male escort; after all, I believe in outsourcing, and in straightforwardly negotiating mutually beneficial arrangements.

In any case, when sex and business start to mingle, there are some simple gentlewomanly guidelines one should follow. Most importantly, don’t initiate anything with anyone who depends on you for money (and don’t interpret the deference and alacrity of an employee for attraction or even friendship).

If I might share a personal anecdote: I celebrated my thirtieth birthday by holding a male beauty pageant in a bar (photos here and here.) Why? Because I can. I rented the space, put up a $200 prize, ordered satin sashes from a pageant company, advertised for contestants, hired male models to hand out chocolates, and contracted the services of a masseur to give free foot massages all night. Overall, I spent $2,000. I didn’t have a swimsuit competition, because men look kind of stupid in swimsuits. Instead, I had a “Mr. Cuddly” round, in which the contestants wore boxer briefs and cuddly t-shirts. Because that’s what I like. I am saying that anyone with $2,000 and access to Craigslist is basically invincible.

A few principles for mixing money and hotness: Just pay people actual money; do not lure them with promises of future work or other shallow, manipulative enticements. Money makes things so simple, at least when compared to favors and promises. (See also Bullish: What to Charge for Your Work and What to Pay Your Assistant.) Of course, do not assume that people want to sleep with you because they are models (that sounds ridiculous now that it’s written down, but plenty of models of both genders can tell you that people make this assumption all the time. People who don’t get that the attraction isn’t mutual are sort of like babies who don’t know that you can still see them when they close their eyes).

With great power comes great responsibility! A teen-sized t-shirt that says “I beat up boys” is just sad. But it’s a totem of a larger problem of people who mistake feminism as meaning that anything a woman has the power to do must be, by power of semantics, empowering.

A gentlewoman realizes that at least 50% of the time people say, “You go, girl!”, they are actually enthusiastically condoning stupid, selfish, impulsive, illogical, or immoral behavior. (Sometimes, of course, they just mean that you are walking in a fierce way in your new shoes.) It is not true that everything every woman does is great. Some women are bad people.

A gentlewoman can do better. Much, much better.