Diary of a Middle Management Sellout: Beefing Up In Q4

Diary,

My man! How long has it been? Saturdays are for the boys! Ha ha! Classic. I know it’s not Saturday, but I’ve been getting tons of laughs from my subordinates/lesserthans whenever I say that at the new job. I gotta fill you in. I finally made it, Diary. Made it to the big show. I am finally management. After doing some part-time consulting in the field for Uber, your boy got his first big time job offer. Oh yes, I’m a manager. It says so on my card. I have three employees reporting DIRECTLY to me and it’s really great to have people I can blame when shit goes wrong. Shit rolls downhill, and I’m squatting bare assed at the top of a mountain.

I’ve checked off an item on my professional bucket list. I’m finally making six figures. My salary starts with a 6, so I’m counting it. So what the hell have I been doing for the last year and a half? Man. Things have been such a whirlwind. I tried getting Steak & Scotch off the ground a few times, but none of my rich friends felt like investing in what my buddy Troy called “Red Lobster for Mark Cuban.” Okay, idiot. You know who would invest in a restaurant like that? Mark fucking Cuban. It was a once in a generation opportunity, and the water under the Golden Gate is freezing cold. Man, can’t wait for that JT Netflix deal.

So, what else has been going on? Oh I don’t know, upgraded to a sick downtown loft. Well, it’s not downtown, but I can see some of downtown from my bedroom. I scrubbed the roommate since I’m hauling down six figgies and I started ordering Blue Apron five nights a week. I have a bunch of rotten food in my fridge now, but my neighbor has seen me getting it delivered at least three times, so she might think Gilbert T. is a man who has his ducks in a row.

Work is actually pretty tough, Diary. I have actual responsibilities. It’s hard to get my work done with all the Westworld subreddits I have to read, so I’m having trouble keeping up. These are the sacrifices one must make if you want to be able to afford both Amazon Prime AND Brazzers accounts. Some may call that “being in over your head”, but I choose to think that my sacrifice is worth it. The good news about being management is that you can buy yourself all sorts of time by going back and forth between “trying a new strategy” and “getting back to basics,” which really just means sitting around until someone emails me and tells me what to do.

I just don’t have any time for anything, Di. My friends are all settled down now. Literally everyone I know got married in the same year. It was insane. You can only wear the same navy suit/brown shoe combo so many times before people start thinking you’re poor. Three of them alone were in Mexico. Had to stay in a Best Western and fly Frontier one time. So embarrassing. I used up all my Southwest Rapid Rewards points to go meet a chick from Chicago I met on Bumble one weekend. She was pretty upset when she found out I wasn’t a “Medical Professional.” My matches have taken a total nosedive ever since I decided to be honest in my pursuits.

What does the future hold for me? I don’t know. Maybe love, maybe Steak & Scotch. Maybe nothing. Maybe I just fade into irrelevance and collapse in on myself like a Chilean mine. Put on some weight, marry a 4, pray to god I never get downsized, buy a split level three bedroom in the suburbs, start wearing Sketchers. But that’s not me. That’s not who I am. I’m a fighter. I’m out here in the trenches fighting every day. But I’ll be around, that’s for sure. I’m not going down without a fight, and Gilbert T. Humplestead fights dirty. So watch me grab this handful of sawdust and throw it right in life’s face, Diary. Watch me.

They have no idea how high I can fly.

Gil

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