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  • Whoa, My Boss Is Naked...
  • Written by Jake Greene
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Whoa, My Boss Is Naked...

A Career Book for People Who Would Never Be Caught Dead Reading a Career Book

Written by Jake GreeneAuthor Alerts:  Random House will alert you to new works by Jake Greene


List Price: $9.99


On Sale: January 22, 2008
Pages: 240 | ISBN: 978-0-385-52532-9
Published by : Crown Business Religion/Business/Forum
Whoa, My Boss Is Naked... Cover

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A hilarious yet savvy career guide for the generation that grew up with remote controls in their hands. (Who knew that you could learn so much about work from American Idol, Anchorman, and Entourage?)

In Whoa, My Boss Is Naked!, strategy consultant (and twentysomething) Jake Greene uses pop-culture references from the ’80s, the ’90s, and today to school young professionals on every stage of the entry-level experience.

Free of cliched motivational advice and bogus “steps for success,” Whoa, My Boss Is Naked! reveals everything you need to know about how to get a tighter grip on the working world without becoming a sellout corporate tool:

The reason most bands suck (why everyone needs to "commit to a sound" before they can get "signed" )
Like, listen to . . . uh . . . yourself talk, ya know? (or . . . why speech fillers are job killers)
 Party on, Wayne (rules for expanding your business network in social settings)
The rules of interview dating (tips to help you score a job)

With its irreverent humor and wisdom from the world of pop culture, Whoa, My Boss Is Naked! proves that career advice doesn’t have to be boring.


CH. 1
Get Up, Get Out, and Do Something


Have you ever watched the same episode of The Real World three times in a single week? Nothing changes. J.T. always gets arrested on the beach for mouthing off to the bicycle cops, and Lavender still breaks down when forced to confront her addictions to sex and flavored lip gloss…yet you still can’t muster up the motivation to change the channel. Your sweatpants stink, the Wheat Thins are stale, and there’s a chopstick caught between one of the couch cushions and your thigh. It’s been poking you for the last four hours, so you’ve gotten used to the discomfort. It’s 1:30 p.m. on a Wednesday…

If I just described your typical afternoon, you should be aware that you may have come down with a not–so–rare case of postgraduation paralysis, referred to in select medical circles as Midas–itis. Midas–itis is a serious psychological disorder that infects millions of twentysomethings every year and is especially common among young people with multiple interests who view themselves as “gifted” or “talented.” The condition is characterized by massive swelling in the entitlement/unrealistic–expectation sector of the brain causing victims to believe that they should only pursue “golden” career opportunities. (*) Unable to quickly identify such utopian employment environments and unwilling to sell themselves short, infected parties inevitably grow depressed and recoil from the real world. Symptoms include (but are not limited to) multiple unfinished movie scripts, untouched graduate school applications, interactive gaming addiction, and/or excessive VH1 viewing.

I caught Midas–itis as a student in Silicon Valley right around Y2K. The Internet was in full boom, and it seemed as though every time I picked up a newspaper there was a picture of some kid (usually not much older than I) who had just turned a computer program into a multimillion–dollar start–up company. Google, eBay, and Napster were close enough to touch, and a constant reminder of the riches awaiting computer science graduates. Naturally, I convinced myself I should study computers, start a dot–com where roller blades and baseball hats were allowed in the office, cash in on a godzillion–dollar IPO (initial public offering), and then ride off into the sunset in a Beemer so tricked out you’d swear it could fly. Only problem: I sucked at computer science. I am not using the term “sucked” lightly, either. I don’t have a single iota of technical talent in my body. I peaked as a computer scientist in elementary school playing “The Oregon Trail” on the Apple IIGS (I was particularly adept at fording rivers and hunting). To add insult to injury, the Internet bubble burst a few months later thereby obliterating my already fading dot–com dream. Even so, I naively assumed that another wave of opportunity would simply wash up on my doorstep, so I waited on the couch and proceeded to lose three months of my life to Behind the Music and PlayStation.

Luckily, Midas–itis is not difficult to cure. In fact, all you have to do is get over yourself and get off the couch. Get up, get out, and do something! Quit imagining what the working world should look like and start experiencing what it does look like. There’s a reason that they call it a “job search.” You need to actively hunt. Will you find a job that allows you to change the world, make millions, and unlock your full range of creative abilities right out of the gate? Doubtful, but so what? Nobody starts at the top. Even Harvard MBAs have to fetch coffee once in a while.

C'mon, would you rather spend the next year out in the world showcasing your talents and figuring out what drives your ambition, or in your parents’ basement trying to figure out which contestant in the “Showcase Showdown” will win a Broyhill bedroom set or drive off in a brand–new Chevy Malibu? Don’t worry about selling out your dreams or wasting your “unique” talents in a windowless cubicle for the next thirty years. The concept of the thirty–year fixed career track expired back when Alex Trebek was still hosting Classic Concentration. So get off your ass and get moving. Ain’t nothin’ to it but to do it.

The Reason Most Bands Suck


Fact: Most bands suck. For every chart–topping Coldplay or Red Hot Chili Peppers, there are thousands of awful bands polluting the stages, bars, and college radio stations of this great country. That is not to say that most bands can’t keep a beat, get along, or stay sober. No, most bands suck because they refuse to commit to a sound and allow themselves to be defined. In striving to dodge convention (and evaluation), these bands end up with set lists that sound like they were lifted off a schizophrenic’s iPod. They might open with a jazzy “composition,” follow up with a Jack Johnson–style bonfire number, and then revive a monster ballad cover, such as Bon Jovi’s “Wanted Dead or Alive.” In the end, all six people who happened to catch the show at Jean Claude’s Coffee Cafe will walk away confused and upset, totally unable to qualify what they’ve just listened to. It doesn’t matter whether or not these bands are talented; all the skill and ability in the world won’t do them any good until they learn to define their sound. In this regard, the professional world is a lot like the music world. If you refuse to “commit to a sound,” you won’t get signed either.

Want a job in finance? Then you’re going to have to commit to becoming a “finance person.” You can begin by watching CNBC and checking out The Wall Street Journal. Or maybe you’d rather be a travel writer? Then you need to start traveling and (you guessed it) writing. Sounds simple, right? Surprisingly, many of the twentysomethings I’ve spoken with are scared of even this minimal level of commitment. They think that by committing to an interest or field, they will be “closing the door” on their other interests and talents. If they were smart, they’d worry less about closing doors and more about getting a foot in one. It’s tough to close a door that was never open to begin with.

Here are a few additional pieces of advice:


Musical artists often combine genres (i.e., “folk/rock” or “hip-hop/ R&B”) to create a unique sound for themselves. Similarly, you should feel free to fuse together a couple talents and interests in order to create a unique professional identity for yourself. You don’t need to focus exclusively on one skill, nor should you limit your search to one industry. However, if you start cooking with too many ingredients, you run the risk of becoming the human equivalent of a “jam band.” The vast majority of jam bands never get signed because they can’t be counted on to produce a consistent product. Their songs sound different every time they are played, their solos often drown out melodies, and sometimes band members get too baked to function. (*) Why would Sony Music want to invest in that? They wouldn’t. Similarly, why would anyone rush to hire a person whose résumé objective reads something like: “artistically inclined, analytically minded modern dancer hoping to pursue a career in day trading or construction”? They wouldn’t.


Back in 1999, Metallica, one of the loudest, toughest, fastest, badass rock bands in the history of music, recorded an album with the San Francisco Symphony. The collaboration promptly went platinum. At first glance, it would seem as though the success of this experimental album completely undermines my hypothesis for this chapter, which is predicated on the need to commit to one sound. However, the reason fans and the industry cut Metallica some slack was because the band had, over the course of its career, developed an ironclad reputation as a loud, tough, fast, badass rock band.

By 1999 Metallica had earned the right to experiment a little bit because its track record was so strong. Fans trusted the band’s ability to entertain, and the labels trusted the band’s ability to sell albums. Similarly, fans and labels trusted Ray Charles when he recorded a country album in 1962, and gave Outkast the benefit of the doubt when it put together an experimental double album in 2003.

Once you make a name for yourself in your profession of choice, you will be granted a lot more leeway for experimentation and diversification. When it comes to landing your first deal (read: job) on the other hand, it is essential that you focus on producing a tight sound. Pick and stick with one angle, one brand, and start building buzz and a loyal fan base. That way, when you decide to branch out later on, you’ll have an audience waiting to listen.

CH. 3
Desperate Housewives and the Era of Free Agency


Before the women of ABC’s hit show Desperate Housewives became überfamous by backstabbing, eavesdropping, and sleeping their way around suburbia, they were merely five second–tier celebrities, jumping from role to role in search of an elevator to the A–list. Lost in the maze of Hollywood mediocrity and craving money, experience, and exposure, they pursued parts in a variety of genres, each hoping to land a star–making role. Between them, the Fab Five of Desperate Housewives took on roughly 160 different roles before landing on Wysteria Lane. That averages out to thirty–two jobs per housewife.

While I doubt that you will hold thirty–two different positions during the course of your career, you should expect to change roles at least a handful of times before you retire to a life of shuffleboard and 4:45 p.m. dinners at the Cracker Barrel. Most likely, the bulk of those moves will happen early on in your career. In today’s fluid employment market, it can take a while before you land a star–making role. Therefore you shouldn’t expect that your earliest gigs will be dream jobs. However, if you stay focused, work hard, and develop your strengths, you can position yourself to take advantage of the star–making opportunities.

There are countless reasons that you may leave a job—or it may leave you—and most of the time it has nothing to do with how talented you are. This chapter will highlight several of those reasons by focusing on early career moves made by the cast of Desperate Housewives.


Sometimes great ideas just don’t catch on with the general public. All the talent in the world won’t save your job if the masses don't dig what your company is trying to sell. Such was the case for Felicity Huffman (“Lynette” on DHW) with Sports Night in the late ’90s. Critics loved Felicity as Dana Whitaker, the quick–witted and outspoken producer on the ESPN–esque satire. Additionally, the rest of the cast was talented, the writing was sharp, and Aaron Sorkin, the “can’t miss” creator of The West Wing, was quarterbacking the whole thing. Sounds like a slam dunk, right? Eh…not so much. The snappy dialogue and “walk–and–talk” scenes that carried West Wing just didn’t play as well with sitcom audiences. During the show’s second season, ABC routinely pulled Sports Night in favor of bonus episodes of Who Wants to Be a Millionaire before canceling the show altogether.


One could make the argument that Marcia Cross (“Bree”) found her dramatic, sexy, backstabbing sweet spot long before she hit the mainstream on Desperate Housewives. In 1997 she portrayed Dr. Kimberly Shaw Mancini, a jealous and conniving spouse on Fox’s Melrose Place. For those of you who never saw the show, Melrose plotlines were eerily similar to those of Desperate Housewives—lots of sex, suspense, plot twists, and slapping. Unfortunately, Marcia joined the cast of Melrose Place when the show was way past its prime. By the time Dr. Kimberly Shaw Mancini detonated the military–strength explosives she had built in the basement, viewers had long since abandoned Melrose in favor of hot new shows like Buffy the Vampire Slayer. So, while Marcia's character blew up after roughly eight episodes, her career didn’t blow up for another eight years.

If the company you work for runs into trouble or their products go out of style, not even an Emmy–winning performance on your part will lead to longevity. I mean, there were a lot of talented people working on the Sega Genesis marketing team in 1994, but they were doomed to fail because their product was being replaced in the market by Sony’s hot new PlayStation. If you happen to join up with an organization that fails to catch fire or is already past its prime, don’t get discouraged. Do your best and learn from the role while you have it.


If you are young, talented, and ambitious, it is likely that you will be “fairly successful” in almost any professional role. Then again, who wants to settle for “fairly successful”? In 1989 Teri Hatcher (“Susan”) got her first big–budget movie role portraying Sylvester Stallone’s sweet yet spicy sister, Kiki Tango, in the buddy–cop action flick Tango and Cash. Though Teri did an admirable job and even created some sparks as Kurt Russell’s love interest, her performance was nowhere near Oscar–worthy. Now I’m sure Teri could have crafted a “fairly successful” career in big–budget action films had she committed herself to doing so, but luckily she didn’t settle. Instead she focused on snappier TV roles that showcased her sense of humor and eventually led her to Desperate Housewives. (*) More than fifteen years later, Tango and Cash remains the lone big–budget action movie on Teri’s résumé.

Don’t settle for a career you might be fairly good at. Play to your strengths and pursue the roles in which you have a shot at being outstanding.


In 2003, just three years after making her small-screen debut as “Flight Attendant #3” on 90210, Eva Longoria (“Gabrielle”) was poised to become a breakout star in Hollywood. In addition to the increasingly large roles she was receiving in movies, Eva had starred in multiple soap operas and also been named one of People magazine’s “50 Most Beautiful People” (Spanish edition). Given her momentum at the time, it is somewhat surprising that her agents, managers, etc., allowed her to take on the role of “Carlita,” a Miami nightclub performer trying to outrun the drug–dealing skeletons in her closet in the appropriately titled B–movie Carlita’s Secret. Can you say “straight to DVD”? Obviously, some executive at the Maverick Entertainment Group gave Eva the pitch of a lifetime and convinced her that Carlita would make her the next Jennifer Lopez.

From the Trade Paperback edition.
Jake Greene

About Jake Greene

Jake Greene - Whoa, My Boss Is Naked...

Photo © 814 Photography

JAKE GREENE is a twentysomething strategy and marketing consultant. Prior to founding Greene Group, he earned a master’s degree in sociology from Stanford University, worked as an analyst for a Fortune 500 company, and served as Director of Client Development for a retail development start-up. He lives in Nashville with his wife, Sarah, and dog, Roger.


“If you are ambitious, read this book!”
– Jeffrey Fox, author of the bestselling book How to Land Your Dream Job

  • Whoa, My Boss Is Naked... by Jake Greene
  • January 22, 2008
  • Business & Economics
  • Crown Business
  • $9.99
  • 9780385525329

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