Diary Of An Entry-Level Try-Hard: Live Free Or Quit Your Job

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You are looking at the face of a free man. Last week, I told IPC where to shove their $37K a year plus benefits. Your boy Gil is gone. Ghost. Dust in the wind. The ol’ Harry Houdini. I’m out, suckas! See you on the flip side.

That’s right, Diary. I finally quit my job. I had it up to here with Terry and the brass at my dead-end job. I’d been polishing knobs and going knuckle-deep in Corporate America’s uterus for 15 months with nothing to show for it. There wasn’t anything tying me to IPC except for 2 percent 401(k) matching and a beautiful mosaic of boogers under my desk in the power cube. But location does not the power cube make, Diary. I’m throwing the saddle on the job-seeking horse and heading for oil country. That’s right. I’m getting in on the oil boom and not a minute too late. Or maybe Silicon Valley. I haven’t decided yet, but you’ll be the first to know when I make my move. But first, let old Gil tell you the tale of how I slayed the corporate dragon.

It all started a couple of months ago, I guess. I’d been trying to make nice with Terry for weeks. We’d been eating lunches together. He even opened up to me about his kids one day. Man, he really hates ’em. It was actually pretty sad. Thought he was gonna start crying into his Firecracker Scallops bowl at Genghis Grill one day. Of course back at the office, Terry iced me out all the time. I listened to him drawl on about his bitch wife and his fat kids for 35 minutes, three times a week. I wanted to talk business! An up-n-cummer (wink) like Gilbert T. only talks about hot deals relentlessly. I’m like the business version of Joakim Noah, but with much better hair. Terry can be such a shithead sometimes. I figured I was due another promotion. I’d been with IPC for more than a year and a half, and all I’d gotten was a lousy cost of living raise and 2,500 business cards.

After a significant amount of brown-nosing, I decided it was time to strike while the iron was hot. I strolled into Terry’s office two weeks ago and let him know that I was ready to take my next step. I completely caught him off-guard, because he coughed up half of the breakfast burrito he had been snacking on all over his desk. Advantage: Gil. I had Terry’s balls in my negotiation vice. After pleading my case (my office fitness initiative, landing deals 24/7, getting my desk nap problem under control) Terry was thinking it over. He glared at me, trying to stare through my soul as scrambled egg tumbled from his chin onto his $12 tie. My outfit clearly cost more than his. Terry was notorious for bragging about how much money he saved on his clothes. I guess you have to find something to be proud of when literally the only thing you’ve got going for you is that you haven’t killed yourself from fat, salt, and sugar. My young, lush, vibrant, perfectly pomaded hairline towered over Terry’s embarrassing cul-de-sac. A little bead of sweat formed on top of his forehead and began to slowly trickle down the side of his fat face. Whether it was from the food or the laser-steady focus of my eye contact, I’ll never know. Terry opened his mouth.


“Well, then I quit.”


That was that. I won. I stood up, buttoned my sport coat, and hightailed it out of there. Your boy was about to test the waters of free agency. I had a solid 15 months of corporate experience under my belt and the calls of upper management in the Texas oil game were echoing throughout the land of Gil. I sped off in the Hump Truck blasting “Break Free” by Ariana Grande. I headed straight to the bar and slapped down the MasterCard. The key to starting any job search is by getting loaded and filling your mind with grand schemes. I sat in a corner booth and opened up my group text with my boys.

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Squad is usually down with a mid-week day rager, but apparently this wasn’t the week. I guess I’d just have to navigate it myself. Of course, the bar wasn’t crowded, but there was still plenty of talent to be had. Common sense says that Saturday around midnight is the best time to get laid at a bar. Nuh uh. Your boy doesn’t throw Hail Marys. I’m three yards and a cloud of cocaine. Your boy matriculates the ball down the field and hits the coverage with play action late in the game. Early Tuesday afternoons — that’s when all the sads come to the bar. There was plenty of sad to go around at this particular lounge.

It was a target-rich environment. There was a 40-something divorcée at the bar, sipping on a martini. She was pushing a buck-eighty, so I passed. There was a decent looking 30-something putting out the sex vibe at the bar. She was curvy, mysterious, and already visibly hammered. I popped a Lincoln in the juke and put on “Tonight Is The Night” by Outasight. It was on.

“Looks like you could use some company,” I said as she wobbled her chair around to feast her eyes on 205 pounds of twisted steel and sex appeal AKA Gil Humplestead. She patted the seat next to her. Game over.

She was sipping on a half-melted strawberry daiquiri. I ordered up two Humplemakers, on the double. She would soon be mine. The second thing you do when you leave a job is engage in sloppy intercourse with a complete stranger. After our third Humplemaker, I was feeling famished. I required food.

“Barkeep, one order of potato skins and some chicken fingers for the lady. You’re gonna love this place’s fingers.”

She was lost in a fog of masculinity and desire. Her glazed over eyes poured over my body, like a mountain lion stalking its prey. It was close to 3 p.m. and the regular crowd would be showing up soon. I couldn’t pass this opportunity up. I was fading fast. My drinking skills had declined due to my professional life. The lights were about to go out at casa de Hump and it was closing time.

“What do you say we have a little afternoon matinee at my condo?” Rule #45 in Humplestead’s Rules of Engagement (coming soon to Never call your apartment an apartment. It’s always a condo.

“Zounds gud t’me,” she lustily purred. I swear “Hungry Eyes” by Eric Carmen started playing somewhere in the background.

Swiped an Uber real quick and we were back on my turf within minutes. She pounced as soon as we got into my bedroom. I heard the box spring snap underneath me as she mounted me. I never thought a woman could rock my world like she could. I didn’t even know her name. It never occurred to me that maybe I should have asked. When you’re in the zone, you’re in the zone.

After our romp was done, she rolled over and slept. I had worn her out. Her growling snores filled the room. I snuck out to watch a little ‘flix and bask in my glory. I had left IPC and landed a feral minx who rocked my world with a celebratory slam session. I soon descended into a deep, satisfactory slumber. That night, I dreamed beautiful dreams.

I was sitting behind an eight-foot wide, stained oak desk. Behind me was a large oil painting of me wrestling a bear. The walls were decorated with the highlights of my life. Me posing with Tony Stewart in the winner’s circle of the Daytona 500. Shooting guns with Shane McMahon in Vermont. Me attending a Mike Krzyzewski success seminar. Fishing in the BVI with Richard Branson. This was my destiny. It’s time to fulfill it.


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Brian McGannon

What do I love? I love happy hour, a good golf tan, and getting moderately drunk during dinner.

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