How to Kill Your Boss

How to Kill Your Boss

by Kerry DeVito


First thing is first: don’t get locked into the choreography of saying, “Do you need anything else?” Because he will always need something else, for what mouse has stopped at a cookie? In fact, try to forget everything you learned about the manners sashay—make sure your boss thinks you’re a hardcore millennial, sucked into screens and intent on answering e-mails with the best set of online social skills the Digital-verse has seen, that you are purposefully keeping from face-to-face time. Don’t act offended when he calls you in response to your 140-character email drafted specifically to elicit a simple yes or no.

The day he comes in to the office at two o’clock, late because of public transportation, don’t mention out loud that morning rides on the local train rarely last into the afternoon. Even in this city. In fact, try very hard to say as little as possible this day, because everything incriminates these days. Keep your face tight when he storms up to your cubicle, in sordid pants and a soggy-looking blazer, a moldy leather bag reluctantly hanging at his side. His scalp, a ceiling mirror, can be seen from far distances, like an upside down flashlight; let this be your warning signal. Your coffee ripples with annoyance.

“One second,” he says, abruptly popping the upper half of his body into your space only to curve his finger in your direction. This means he needs something from you.

His office, a windowless room of brick and concrete that one day will be decorated in yellow tape, can be considered a saint, as far as you are concerned. St. Office of Broken Souls. When the door closes and his voice is contained for an hour or two, you want to kiss the door handle and plaster yourself against the wooden slab in a flat hug. Thank you. Thank you for shutting him in.

He sits in his chair and pulls out a packet of papers that you printed for him not that long ago. The corners are bent inward like ears, and a small brown spot blossoms from the center. He stabs his finger almost through the paper, flicking an area on the map of the building. You highlighted and circled the words “floor four” before handing him the basic floor plan yesterday evening after his announcement of “the big morning meeting.”

“Where the hell is this?” He speaks like you’re the subpar architect.

You don’t need to look twice to know this is the floor below yours, mostly because of the number four written at the bottom of the map and the number five you press every morning on the elevator ride.

“I believe that is the…” you say, keeping your hands folded behind your back. You lean over his shoulder to make it seem as if you are studying the map. “Third floor. Yes, that’s the third floor.”

He doesn’t seem to notice the two darkly drawn arrows you strategically placed under the number four, typically something of a giveaway.

“This is the third floor? I don’t understand.”

You smile and your head tilts left. Silly, silly balding man. But perhaps his brain is receding, too.

“Look,” he says, leaning back in his chair. It shrieks a tiny plea. “I think you’ve given me the wrong map. I just went to this so called ‘third floor’ and came across no conference rooms that looked like they were ready for a meeting of this caliber.” He brings two fingers up and bends them once at the knuckles for extra emphasis. Take note of this because, even though this may be the end of his second month on the job, he still has weird, nervous twitches.

As the VP administrative assistant, it is your responsibility to kick kiss ass from nine to five. It is actually in your job description: “At least 3-5 years experience with professional buttock smooching, particularly at times when VP is utterly and overwhelmingly incorrect about where meetings are held. Must be comfortable with giving up personal goals and passions to better serve the smooch-ee. Should be willing and ready to hand over every and any potential beneficial idea to then be accredited to VP.” So when your boss tells you that this company, a company that he has belonged to for less than ten weeks, is not well equipped for “high caliber” meetings, you must agree.

“Would you like me to call the other VPs and re-schedule for a different conference room? An entirely different building, perhaps?” Would you also like me to teach you how to count, starting with numbers one-through-ten?

            He sighs heavily.

“There’s not enough notice. I’ll need you to escort me to the meeting.”

Must have 1-2 years experience in escort service for high-level professionals.

“Of course.”


Typically the commute back to your apartment does not end in rage, but on this particular night, smoke and red surround you, and it is not the screeching cars or sewer steam. You reserve Tuesday nights for a painting workshop at the small art supply store down the street. It would have been your first class, but someone needed to scan the boss’s receipts from the past week. You’ve calculated these numbers, plucked them like ripe berries from the wrinkled slips of paper and plugged them into a plastic calculation to find that, in just one month, he’s spent upwards of ten thousand dollars on dinners and taxis and hotel rooms on the company card.

May be required to keep secrets and make up lies to feed to VP’s nosey wife.

Walking back from the subway you stop by the art store and peek through the frosty windows. There are four older folks sitting around a table dipping and dabbing paint brushes while the instructor, a young man, stands in front of a canvas, talking and sweeping green leaves onto a tree branch. His hair is curly and mopey, almost reluctant to cover his head. He sees you in the window and catches your face in guilt-mode—you never wanted to be this corporate bend-over kind of person. Not you, the girl with unwashed hair and noisy silver bangles and long skirts with dirty edges, charcoal bleeding from her fingertips and old cups of coffee scattered around her dorm. Make yourself a note: if you are ever offered the chance to go back in time, don’t. College you might feel murderous.

And so you open the door to the shop, slowly, so the bell doesn’t get too jingly. It’s a small place, too small for packed aisles like Wall-to-Wall Mart. Instead it is really just a room, the walls lined with carefully placed paint bottles, canvases organized by size, sketch pads, charcoal sets and boxes of pastels. There is a young girl sitting at a desk close to the window, her hand propped in her chin while the gum in her mouth expands and explodes. She hears the tiny jingle.

“We close in five minutes,” is all she says to you before twisting around in her seat again to watch the class. Her dark hair is wrapped in a perfect bun, several pins make sure no strand is out of place, and her shoulders slouch forward in a plaid button up.

The paints are over behind the instructor, so you decide not to walk by the workshop and distract the participants sitting at the table with the extra empty seat. Instead, the charcoal catches your eye and you think, This is nice stuff. You remember accidentally rubbing it all over your nose. You never realized until you got back to your dorm and saw what looked like a coal miner staring at you from the mirror.

The instructor speaks about watercolors and someone in the class says something, funny apparently, because another participant laughs and it twists your stomach into a rag because of the way it sounds just like the guy you work for. Jesus, they’re everywhere, those reminders. The screech of cars breaking in the street, the lopsided sag of your bed, and the smell of overcooked oats your roommate makes for dinner every night. You quickly pick up a sketchbook to make yourself look occupied and not like you’re trying to get in some watercolor pointers for free. But you did pay for the class; it’s just that nobody knows you’re the one that is missing.

You are so engrossed in the smell of the paper inside the sketchbook that you actually drop it when you feel someone tap your shoulder. It slaps the concrete floor with its exterior shell, and you whip down to scoop it up and hold it tightly against your chest.

The male instructor stands behind you with a look of something between concern and confusion, topped off with a fistful of uncertainty.

“We’re about to close,” he says, bringing his hands awkwardly into his pockets. He stares at the sketchbook in your hand. “Are you going to buy that?”

His hair is so out control it seems to be the one with the voice.

“No, I don’t think so,” you say, loosening your posture and trying to fit the book back onto the shelf.

“We have a strict you-smell-it-you-buy-it policy here. No exceptions.”

You try to smile, because you’ve only been caught page sniffing once, and maybe this guy will think it is a little normal. But your upper lip is too dry and gets caught on your teeth, giving you squirrel-face. He doesn’t seem to be joking. You buy the sketchbook.


Back home, in the dirty light of your bedroom, you place the sketchbook on your desk and sit across from it on the bed. A slow re-introduction is best, you figure. But then you remember reading an article on your lunch break about the three types of burnout: frenetic, worn-out, and under challenged. You dropped your peanut butter sandwich on the floor when reading the descriptions of the types, mostly because you fit every single one, but also because the last one was enough to rip through your guts and pull out your tired soul, shove it in your face and say, See? You really are dying.

Symptoms of impending soul expiry might include but are not limited to:

  1. Consistently under challenged by a challenged boss.
  2. Easily worn out by things that typically substantiate.
  3. Frenetic feelings that may lead to frantic soul numbness.


The sketchbook is basking in your realization that you need it so desperately. You need to open it again and smell its insides, touch the pages and get goose bumps from the feel. It could even be smiling at this point. In fact, you think there is a slight snicker floating off of its black cover.

Your digital clock, an unpleasant thing to behold just because of its job to keep you moving in circles, has numbers for you—it’s too late to begin down this path. You stand and walk to your desk, shove the book in the single drawer and allow the spiral spine to get caught. You wouldn’t have bought it anyway if it weren’t for that mop-headed instructor.


The next day at work, all hell has broken out of its subterranean shell and landed in your office. A VIP (Very Insignificant and Pestering) stakeholder has called your boss directly to complain about the lack of communication he has received in regard to his most recent investment. Email chains are being sent with red exclamation points and phones are ringing more than usual. Now a lunch appointment must be set up for the following week, at the local fancy spot—Steak N’ Chop. You accidentally write down “Stop and Shop” during your one-on-one meeting with the boss, and he brings his own pen down to forcefully scribble lines through the words.

“Steak. N. Chop,” he says, taking three seconds to pause after each word. “And get the booth by the large window, I don’t want him to feel confined. I want him to feel like his investment in our product is something that can take him places.”

You want to suggest a place with more options than just steak fileted or chopped, but really, mum is the best word. You scribble “window booth” and “take him places.”

“And I’d like you to be there,” he says, bringing his pen to your notepad again, this time writing “big” in man-child fashion before your window booth reminder.

You sit up, surprised. “Oh.”

“To take notes. It could go for an hour or two, so you better eat lunch beforehand.”

You stare at his chubby neck for a moment.

“Do you need something else? I think we’re done here,” he says, flicking a finger towards the door.

You rise and try not to impale yourself on the corner of the door.

Back in your cubicle, the noises of lunchtime ensue. You reach into your bag and grab your sandwich, though it takes you a moment to find it. There is something different about your bag today—the canvas is stretched taut on the outside and there is hardly any space for your hand to dig into it. You pull out your squashed peanut butter sans jelly sandwich, and the black sketchbook. There is something strange about this because, unless you sleep sketch, you do not remember taking the book out of your desk. And yet, the sketchpad is here for you, taking up space next to your sandwich and water bottle, kind of like a lunch buddy.

You contemplate and chew, watching the black book sit on your desk. And it’s strange, seeing it there, mixed in with this stale environment. It must know that it doesn’t belong here, but wanted to come for the ride and see what you’d do with it. Would you take it out or leave it in the bag? Would you open it? Would you even see it?

You saw it, you took it out, and now you’ll open it. You thrust open a drawer you keep full of supplies and take out a pencil, sharpen it and plant it on the first page of the sketchbook. The point snaps from the pressure, and you want to break the yellow stick in half. But something about this hellish day brings you to sharpen it again; taking the time to make sure it is not too sharp, not too dull. This time you apply it lightly to the page, and something happens that surprises you.

Your hand moves. Your hand and the pencil flow, brush over the page, stroke and hatch, cross and dot and shade until the page is covered and the lunch hour has gone by with just one bite taken from your sandwich. You look at your lunch and flip the page, begin drawing the bite marks you’ve left in the bread. Then you notice the intricate folds of the plastic wrap, the dark and light of the shadows that cover your desk, the pattern of your bag’s zipper. The way your left hand lays calmly, stabilizing the sketchpad while your right hand works furiously, brings more emotional than anything you’ve experienced in a very long time. Everything is new.

“Did you get those reservations? I’m taking off, try to get in a little earlier tomorrow, yeah?”

Your boss’s face looks down at you from over the cubicle’s wall. You can only nod because, as the clock behind his large head would have it, four hours have gone by since lunch.

Flipping through the pages you’ve filled up in the sketchbook, your mouth hangs open a little—there are at least ten full sketches, with detailed lines and shadows. And all of these sketches, except for the first two pages where you’ve just drawn in thumbnails of your lunch and hands and strange patterns, are of your boss’s funeral.

The first is of a headstone, engraved with his name, birth and death dates, and the words “World’s Best Boss.” There is a bouquet of wilted flowers at the base, sitting in his favorite coffee mug and drooping over the edge. The next two drawings are of his wife standing over his grave solemn at first, and then smiling and waving a happy goodbye. The very last sketch is one you probably should consider not safe for work—an onion shaped gentleman sits at a table beside a large window, overlooking the city street, choking on a fine hunk of steak. He sits with a napkin tucked into his shirt, a fork and knife in each hand. The eyeballs you’ve drawn in (expertly, if you do say so yourself) are popping out in choking fashion. Surrounding are three plates of steak, a large bowl of what looks like home style mashed potatoes, and a bottle of wine. But perhaps what is most horribly satisfying is that you are also drawn into this scene, staring directly out of the page. You appear to be waving, and with a small smile. The same mug from the earlier sketch sits in front of your empty plate.

Before you leave for the day, you make a quick call to Steak N’ Chop, reserve the large window booth for three, pack your sketchbook and go. When you arrive back to your apartment, you ignore your roommate’s polite questions from the kitchen and head straight to your room. You flip a light on and dump out your bag, the sketchbook toppling out last. It lies still on your bed, surrounded by a pulse of energy that you can actually see. It needs more of you—you need to give more.

And so you give the sketchbook more. Every night after arriving home you take a pencil and funnel yourself through the device and let it explode onto the whiteness of the paper. You feed and fill it and in return it gives something back to your soul. You draw a series of separate events that lead to several different version of the death of your boss, things like scissors through the gut, a severe scalp sunburn that ended in torched brain, suffocating on hairballs resulting from licking a client’s suit clean, and drinking a cup of coffee made from exotic poisonous java beans. You place yourself in each one, waving from the corner, peeking out from the top of the page, poking your boss in the face while he suffers from brain melt. And in each scene, you’re smiling.

You only recognize the shift from night to morning when the sun begins to leak onto your paper, and you know that it’s happened again. Sleep begins to seem like somewhat of a luxury. But you’re on this roll and it is making you feel high, higher than a raise or promotion could ever get you. It’s already been a week since you started this kick, and you’ve run out of room in your sketchbook.


You arrive at work a little later than usual. You toss your things in your cube and hear a grumble erupt from your boss’s office.

“A moment,” he says.

You walk in and sit down, realizing that you don’t have a pen or notepad for notes.

“I need you to get to lunch before our client and I,” he says, flipping through some junk in his drawer. “Make sure everything is set up and ready for us. Order the food and wine, I don’t want to wait too long for it.”

“Will do,” is all you say, mocking his nasally voice. You think it sounds funny, and it is actually quite the spot on impression. It took a small gurgle in the back of your throat to get it just right. You really can’t help but laugh.

He looks up at you from his desk.

“Something wrong?”

You realize this is the first time he has ever made eye contact with you before. You kind of feel like you are about to burst into a very large fit of laughter—in fact, there would be nothing more satisfying than rolling around on the floor snorting in this guy’s presence. What would he do? Would he act like nothing weird was going on and ignore you like parents do with two year olds in the candy aisle? He might mistake it for a seizure and call an ambulance, which would end up costing you two hundred dollars.

“No,” you say, gathering your mind and dragging it back to the present. “Is there anything specific you’d like me to order?”

“Steak,” he says.


An hour goes by and you have to shove the loose-leaf drawings you’ve been working on into a file that sits on your desk. Even though your sketchbook is entirely full, you still carry it around with you everywhere. After you arrive at the restaurant and are seated at the correct booth, you order some wine and steaks and the family style vegetable for the table and whip out your sketches. You have a few minutes to kill before the guests arrive.

You’re penciling in the final details of your boss’s forehead wrinkles when you see them walking up to the door. Quickly you shove your drawings into your bag and pour them each a glass of red wine. You refill yours and flag down the waiter for another bottle. Things are a little blurry.

They take a few minutes talking to the host, hands rising and clapping backs, laughter floating around like the greatest of introductions. He begins to lead them over just as the waiter drops off the wine and refills your water glass. He tells you the food will arrive momentarily.

Your boss sits down, red faced from the tightness of his tie. The client, who introduces himself as Peter, needs a second chair to elevate his ankle. A skiing injury, he explains, is one of the absolute worst things to experience on a business trip. Business and pleasure, as they say.

As you soon discover, business lunches are no more casual than a regular old meeting. Your boss signals to you when its time to start taking notes, and rather than panic when you realize you’ve forgotten to bring your notepad, you simply pull out a wrinkled sketch and date the back of it. Your boss’s forehead creases deeper, and you notice a bit more shadow than before.

“Now, everything we have talked about, Peter,” he begins, pinching two swollen fingers around the stem of his wine glass, “remains the same. Your investment matches up with the others, there is no special treatment here.”

You doodle furiously. “Treatment” becomes floating candy bars and peppermint swirls, “investment matches” becomes a matchbox decorated in a dollar bill pattern. Soon the matches start to dance out of their box and strike the side, light fire to the wine glasses, initiating a glass explosion into your boss’s eyes. Gio dances around on one foot and lands on a neighboring table, his hand smashing into a bowl of mashed potatoes. Ladies shriek in horror when they see a pair of conniving flames dance around your boss’s shiny head and melt his skin.

“Hello? What are you laughing about? Hello?” Peter nudges your elbow and you notice your boss staring maniacally at you.

“What the hell is wrong with you today?”

You don’t recall laughing out loud, but the waiter arrives with lunch before you have to explain yourself.

“Six steaks, two bowls of mashed potatoes, and a side of green beans. Can I get you anything else?”

“No, no, fine,” says your boss, shooing the waiter with a small flick. Peter reaches for a cut of filet and a large helping of potatoes.

“Would you like some?”

“Oh, no. I’ve eaten,” you say, even though you forgot to and have been sucking down wine for the past half hour.

“So, you’re just here…to take notes?”

“Well,” you begin, trying to think of a way to make yourself seem more valid. “I take very good notes.”

You squeeze out a wink at him, though he probably mistakes for a twitch.

Across the table, your boss is silent. He is shoveling steak into his mouth like no animal you have ever seen, and wastes no space. He doesn’t wait to swallow before scooping in potatoes and green beans. You watch him and wonder what it’s like to be his jaw.

And then, in a terrifying moment, he opens it to speak.

“’Ow, Pete, what do you ‘fink ‘out havink ‘ly all?”

Peter stares at him a moment, and then simply shakes his head.

“I’m not sure what you are saying to me.”

It strikes you that your boss should never conduct a lunch meeting, or any kind of lunch in public view, if he eats like this.

“’Ay wanna ‘ab a ‘all ev’we ‘ek.” He fills his mouth like a pothole.

Peter shakes his head again, pushing his own plate back.

Your boss looks to you.

“’Splain,” he spits, jerking the fork-hand in Peter’s direction.

Explain. Explain everything.

            You shift in your seat a little, facing Peter more directly.

“What my boss is trying to say, here, is that he thinks it would be a good idea to have a weekly call with you. A status update, if you will.”

Speaking for your boss is much easier than you ever could have imagined. Maybe even a little bit fun. So you get enthusiastic.

“In fact, I personally think this would be a great opportunity for you,” you say, as Peter nods along, “to learn a little about our friend here.” You gesture to your boss, but he doesn’t seem to notice since you are not made of steak or steak sauce.

“When we have our weekly meetings, I typically take diligent notes. But recently, I’ve started taking doodles instead.” You take a sip of wine and shake your head.

“Yes, doodles help a person retain much more, didn’t you know? ‘Doodles Are a Dude’s Best Friend,’ I think the article was called. In any case, this guy here is a real quack, so I’d be careful with any money I throw his way. You know what he used the last batch you gave him for?”

Peter is distressed at this point, and his face turns from intrigued to angry.

“What is she—”

But he is interrupted by an alarming gargling noise that certainly is not coming from you. Your boss desperately is trying to speak, but there is far too much meat in the way of his voice, so he sputters and spits like a broken car. He waves his hands, still clutching the fork and knife, in an attempt to get you to shut up.

“No, no,” you tell him, hugely satisfied that he is choking on his lunch. “You told me to explain.”

“What did you do with my money?” Peter has taken his injured ankle off its seat, gently placing it on the floor next to the non-injured one.

“He used it for his own investment, Peter,” you say, calmly. “He purchased his wife—”

There is a large thump as your boss falls sideways off his seat, making gagging sounds as he writhes on the floor. Peter leaps to his feet but is not sturdy enough and falls back onto his chair.

“Help! Does anybody know the Heimlich?” Peter waves his hands in the air and looks around frantically. The restaurant is half empty and the host runs back to the kitchen. A waiter comes over and drops to his knees over your boss.

“Sir, are you alright? The host has gone to find the Heimlich instructions, please hang on!”

No one else knows the Heimlich here except you. You took CPR and Heimlich classes in high school for babysitting certification, a useless piece of paper that got you crappy hourly paying jobs. And here you are, babysitting still for just as terrible of a paycheck.

There is still a bit of wine in your glass so you finish it, and Peter’s too. He has managed to crawl his way over to your boss and is holding a hand up to his mouth. The waiter jumps up to find the host, who still hasn’t come back with the instructions.

It doesn’t seem that anyone has called for an ambulance, which is just as well because you’d probably end up paying for it. Instead of waiting around to watch the bucket be kicked, you pack your doodles and walk out of the restaurant, slowly, just in case they do actually find the Heimlich manual.

Peter announces, “He’s turning blue!”

Just as you open the door to leave, you feel a little breeze snake into your hair and around your waist, and you let it dance around you as you stand in the doorway. You close your eyes for a moment, until you are ready to step outside and close the door.

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