The Official Preppy Handbook: Failing Upwards

The ability of some people to fail upwards is one of my favorite topics because I’m fairly certain I’ve never pulled it off. This is not to say, “I certainly haven’t failed upwards; I’ve worked hard for everything I’ve got.” It simply means – I find myself working hard but not necessarily realizing the meteoric rise some others do and there is definitely a lack of free stuff being showered upon me. For me, I’m sure this has to to do with personality. There are some people who are born self-promoters and/or bullshitters and I’m not one of them. But enough about me. The Handbook says, “Only those who continually fail to strive and to succeed are rewarded with the respect reserved for the upper crust.”

Failing upwards starts in prep school. As in, Preps get kicked out of one choice school only to surface at another, hopefully more elite, school. It’s practically shameful to graduate from the first prep school you went to. You must embroil yourself in a scandal at least once and then bravely depart, secure in the knowledge that your family money and connections will land you in a better situation.

Now, you don’t want to push it so far that you end up in a public school but it’s perfectly fine to get kicked out once, twice, even three times (a lady). Only one of these should be for drug use though. One drug-related kick-out is fun and games; two or three and you get a rep for having a bit of a problem. Also try: cheating, flunking out or spectacular pranks as means for expulsion. The Handbook names Humphrey Bogart, John Cheever (again with the Cheev!), Christina Crawford, Bette Davis, Steve Miller, J.D. Salinger and Brenda Vaccaro (yeah, who the hell is that?) as famous prep school drop-outs.

What if you’re way past the age of prep school and just now trying to establish your Prep Cred? Get fired from your job. The only caveat here is that you must find a better job than the one you leave or the whole thing blows up in your face. Getting fired and ending up at a lesser job means you are socially dead and not, obviously, failing upwards. If you don’t want to get fired, exactly, at least get caught up in a scandal that could lead to jail time, from which you somehow end up neatly extricating yourself, keeping your job and then getting promoted or starting your own business a few months later due to higher name recognition.

So, what are some acceptable Prep professions in which to fail upwards? First, some of my favorites:

Art dealer/Gallery Owner – people will be mostly mystified over how you manage to make any money at all, especially in this economy. A great job if you majored in something like Philosophy. Don’t major in Art History or Fine Art! You don’t need to have any knowledge of art, really, you just need to know people. This way, when your first gallery fails, you open a bigger and better one with a financial backer who, for reasons known only to them, believes in you. This is a great profession for women who went to any of the Seven Sisters schools. Inevitably, the gallery closes once a woman has a baby and decides to become a part-time art dealer who works from home. But that’s OK – it creates a void for the up-and-coming prep who just graduated!

Philanthropist – OK, you have to have some wealth for this one but it’s a great gig if you can get it. Serve on nonprofit/charity boards, chair fundraisers, travel to third world countries to “observe devastation” personally AND set your own hours.

Public Relations – There are some set parameters here. You want start out working for a respected firm, representing luxury goods, artists, actors or tech companies. You certainly don’t want to be doing PR for Tires Plus. If you’re a lady, you need to be the PR director for a hot clothing designer and make sure your job requires many trips abroad. If you’re a guy, you want to rep Ferrari or Porche or a menswear designer who makes expensive trench coats. Anything to do with “top shelf” liquor is great (but don’t ever call it “top shelf!”) But at some point you must become embroiled in a scandal complete with an e-mail trail, photos or a crime, be in the news for at least two months, disappear and then reappear about three months after that with your own company!

Nonprofit Director – You will appear to be altruistic and this is OK, since many top directors still pull down some serious cash (notice I’m not talking about anyone who works in any other position at a nonprofit). Plus, if you position yourself in just the right way, you can appear in ads for organic things or jeans and win contests in magazines for being hot, single, altruistic AND adventuresome. Within five years, you must start your own nonprofit organization that addresses a very specific cause that is close to your heart. Keywords to consider when deciding what that cause will be: children, art, autism, green, environment, gorilla, dolphin, ocean, air, ozone, Africa, female mutilation, entrepreneur, dance, United Nations, bamboo, blood diamond.

The Handbook also gives these options: lawyer, stockbrocker, ad account exec (it notes that this is the only acceptable position in advertising although this was pre-tech boom and pre-Internet), investment banker (ah, the 1980s!), editor, furniture restorer (now I think you’d want to make that furniture designer, bonus if you use corrugated cardboard!), tennis pro, rancher, yacht designer and ne’er-do-well (think Jon Gosselin in personality but certainly not in circumstances. Eight children?? Not preppy!)