08/29/2013 05:34 pm ET Updated Oct 29, 2013

The Miley Dilemma

If you're going to be a big-deal female pop-media personality in America, you've got to swallow the following trio of bullshit truths:

A) From age 5-17 you're a paragon of innocence, neat and nice and non-threatening and ultimately very Christmas-Card-like. Chances are it's the Disney network that's making you famous, so it's the Disney brand to which you must conform. Everyone is supposed to want to have kids that are like you, so you need to embody that fantasy for them -- except they probably don't want to deal with your near-total dedication to image management, your grueling schedule, your obsessive, Michael Joyce-like cultivation of your very particular talent, so you can never draw attention to any of that. Also, if you're 16 or 17, everyone is going to pretend you don't have breasts, even if you yourself are also still trying to wrap your head around all that.

B) From around 18-35 you're comically and perpetually sexualized in ways that are wildly non-normative, except that people everywhere have agreed to act as though they are somehow normative and treat them as such. Nobody looks like this in real life and nobody has sex like this in real life and nobody has ever appeared sexy by acting like this in real life, and yet we all agree to view performances like this as way less clown-like than they objectively are. "We are all smoke and mirrors," actress Ginnifer Goodwin once said, speaking for an industry. This is your life.

C) From something like age 36 on -- with rare exceptions for transcendent beings like Madonna or Angelina or Nicole Kidman, but not for e.g. Cher -- the reality that you have sex has become the subject of comedy, uncomfortable honesty, or an Oscar nod. Your sex drive is assumed to exist in the way that the need to occasionally blow your nose is assumed to exist, but it's never front and center unless you're making a statement about the fact that it's front and center. You are frequently "beautiful" but never "sexy." Eventually you become Oprah or Blanche Devereaux or Jodie Foster or "M." Watching this transition happen to Gwen Stefani has been nothing short of mind-blowing.

The trouble comes when you have to transition between these stages, at which point everyone loses their minds.

At the top end, it's rarely a huge pop-cultural obsession (except with someone like Gwyneth Paltrow, who -- to reinforce an earlier point -- was People's Most Beautiful Woman this year, and regularly releases cookbooks); rather, what becomes evident is that a given starlet's personal branding team starts to have no idea what image they're supposed to be building. This first occurred to me around the 1998 release of the (awesome) Blondie song "Maria," the music video for which seems to be oblivious to the fact that the totally-iconic Debbie (Deborah?) Harry is a member of the band. But you look at people like Chrissie Hynde and Dolores O'Riorden and (somehow) Liz Phair, and suddenly it seems like no one is willing to cope with the presence any kind of sexual identity within this group. The stock response is along the lines of "Well, some of it has to do with motherhood" -- but that's no small amount of ironic, am I right?

The transition from "a" to "b", though, is where all hell breaks lose.

In stage "a", you're sexless. In stage "b", you're oozing sex -- and it's not regular sex, it's a hilarious caricature of something that only vaguely resembles sex. If you're lucky, you're getting famous solidly inside stage "b", and no one finds it odd that your entire career involves playing a role that's one part yourself and one part bonobo monkey. It's when we see that transition happen before our eyes that we're forced to confront the insanity of it all. Instead of looking inward, though -- we project.

All of which is to say: I think Miley Cyrus' VMA performance totally ruled, and was totally awesome, and was a successful indictment of all the absurd societal constructions that have defined the environment inside which Miley became a cultural juggernaut. It made me want to listen to Ke$ha and the Beastie Boys. It made me want to give her a high-five.

People keep arguing with me about whether she was being ironic. That is like arguing about whether it was Toni Kukoc or Steve Kerr who defined the 1996 Chicago Bulls. People also argue that it was a publicity stunt -- that her ability to "titillate and appall" millions made her the "real winner" of the night. This is like arguing whether it was Jordan's film career or his Nike contract that made him the greatest player in history.

It wasn't about irony. It wasn't about publicity. It was far more transcendent than that.

She certainly wasn't trying to make some kind of statement about having "grown up," which is what everyone inexplicably keeps trying to say. Nothing about anything about that performance was at all "grown up" -- the hilarious tongue acrobatics, the punky not-quite-dancing (let's all do ourselves the service of reserving the word 'twerk' for actual twerking, or at the very least for a timely Ying Yang Twins reference), the kick-ass Foam Finger of Doom. Nor should we think she simply doesn't realize this, because the tone was obvious: it's a natural extension of what we saw just a few months ago in a certain unicorn onesie.

Richard Fry gets it more correct when he says she delivered a "brilliant, funny, and confident" performance -- but he hits his stride right here:

By the time Robin Thicke appears...the stage already belongs to Miley. He has wandered into her territory like a little boy about to lose his lunch money. She bends over and playfully rubs up against him and then she is gone...This is Tank Girl versus The Misogynist Of The Year. She is not there for him like the girls in his video, she's running the show.

What Miley Cyrus was doing at the VMA's, plain and simple, was trolling an entire industry for marketing a manufactured dissatisfaction over who she is -- even though she has built a career off of following their formula at every step!

When she was a kid, she played the kid. Then, she turned 18, and started acting (and dressing, and behaving) like every pop star her age.

"OMG," we said. "She's making me think about sex!"

And that makes us uncomfortable, because we remember the time when it wasn't okay to look at Miley Cyrus and think about sex. So we blame that discomfort on her.

Well. You can't be a kid anymore. You can't be sexy, either. You can't be "a". You can't be "b".

So who can you be, then?

You can be Miley.

You can be the woman who has lived through the transition -- the kid who has become a starlet. You've played both roles superbly, and now you're realizing that the whole of you is more than the sum of those parts. So you'll take that iconography of innocent childhood, and you'll troll it, and you'll mock it, and you'll take that iconography of pop superstardom, and you'll troll it, and you'll mock it, because neither of these categories successfully contains you.

Instead you'll own them both, and make them yours.

The kind of partying Miley was singing about on Sunday wasn't the same partying she was doing in the USA. But it shouldn't be , because it would be weird if that was still who she was today. The song -- despite all the artifice of it -- is a paean to brainless hedonism, which should clue us into the kind of comical self-consciousness the entire performance was about. It's about the ridiculous standards we as a society have for people that spend the first half of their career having to market themselves as innocent family-programming icons, and the latter half of their career having to market themselves as exaggerated-performative-sexuality icons. About how Miley has been panned and slut-shamed in ways that never would have come up if she wasn't a kid star first. About how she's going to do things her way this time, because she's not going to please everyone regardless.

If this makes all of us uncomfortable, perhaps we should be looking in the mirror. My friend Ferrett Steinmetz recently wrote an article encouraging us all to get a lot more comfortable with raising children who 'know where their bliss is,' and who know what they need to do to discover it. That's a good start: acknowledging the sexual reality of every person rather than hiding from it. But let's also work hard to realize when our expectations are just that: our expectations.

I'm the COO of an organization that works in high schools across the country. Sometimes our kids come up to our Dream Directors and want to talk about their sex lives. This is awkward for everybody and is a source of much discomfort and squirminess and consternation. It's also a perhaps-unparalleled opportunity to get very real and very personal with a student, and resolve a very real and very personal problem, and provide safety within a space of comfort, and (on the best occasions) radically transform a life. We would be shooting ourselves in the foot if we pretended this vital and vulnerable part of them was not a part of them.

So no: I don't judge Miley. I thought she looked cool and had fun and made a statement. I dug the bears. I dug her hair. Occasionally she acted silly and occasionally she acted ridiculous. But the whole time I knew exactly what I was watching, which was an experience that no one else on Earth could have quite put together. It wasn't a blend of the juvenile and erotic, but instead a co-opting of them both, an assertion that neither of them together was quite accurate to describe the woman whom they both define.

Up there on that stage, she was just being Miley.