Diary Of A Middle Management Sellout: Checking In

Diary Of A Middle Management Sellout: Checking In


Oh my GOD, dude! What is going on? It’s been a wild last few months, Diary. Absolutely wild. Free-for-all. My quantum leap into management has gone off without a hitch. Well, that is unless you don’t count the trip to HR because of an unsanctioned intern battle royale (prison rules) at the company Christmas party. Pro tip: Don’t mix nog and rosé. Those are seasonal for a reason. I put the blame solely on our office manager for that one. What an idiot.

Regardless, I’ve really impressed some of the brass here at the new company. It’s a startup (nbd kbd) and we have this baller office down in an old abandoned milk factory. These people love me. There is literally no such thing as good ideas and bad ideas, probably because they’re terrified of being sued. We have a weekly strategy meeting where we all sit around and talk about things like “growth hacking” and “mock vortex principle” (seriously, what the hell is that). I’m not entirely sure anything gets accomplished in these meetings, but whatever. They usually get me to lunch every Wednesday, so I don’t complain.

The last seven months, every time I’ve been called on in meetings I’ve switched back and forth between “forging a new strategy” and “getting back to basics.” The CFO loves it every time. Eats it up. If the company asked me to prove my profitability as an employee, turn off the lights. Party’s over. Old Gil’s hitting free agency with a fat severance check and maybe even some equity. Doesn’t sound so bad. Maybe that’s my end game here. If I want to retire to Montana, Tempe and Islamorada before I turn 50, someone’s really gonna have to screw up and I’m planning on it not being me.

Humplestead’s Rule #34: Life is an endless game of chicken where people just try to not get sued. Don’t be the first one to blink.

Anyway, since I’m technically a director, I was sent to a leadership seminar in Boca Raton (so baller).

Before I get to that, I guess I should catch you up on what’s been going on in my life. First off, I’ve got this choice condo downtown now. Well, it’s not downtown, but I can see two buildings in the skyline from my apartment. That’s what I tell chicks, anyway. They eat it up.

Speaking of chicks, my love life is kind of on the rocks. But my thrust life has never been better. I am on such a hot streak lately, I’ve been leaving tracer burns on mattresses all over my zip code. Apparently chicks get real hot over dudes who drive certified pre-owned 2012 GMC Acadias. Who knew?

I’ve currently got two broads who I’ve been seeing regularly. The first one is my sandwich artist at Subway. I’ve been eating fresh for lunch and dessert (wink) for the better part of three months now. I think she’s a recovering drug addict because of her weird body, but I haven’t paid for an Italian BMT since March Madness, so you tell me the risk-reward on that one. Things haven’t gotten all that serious with my cold cut enchantress. Mostly because I think she could go back to prison at any moment. So I’m playing that one pretty close to the vest.

My second steady hook up is a real spicy goddess. I don’t know her technical ethnicity, and frankly, I don’t care. Gil Humplestead is a 21st century lover. I’m an equal opportunity kind of guy. She works at Chipotle and hooks it up on the reg. I’m talking double meat, double cheese, throw in a side of guac on the house. Who loves you, baby? Gil, that’s who. Her name is Anastasia, which really throws me off. She could be anything. Straight up American, Hispanic, maybe even Russian. I base that solely on the fact that my knowledge of world history is comprised from ‘90s movies.

After polishing off my weekly chicken and chorizo burrito last Thursday, Anastasia got pretty serious. She asked me if I saw our relationship going anywhere as she gently stroked my lush, greasy gut hairs. I told her I was too full to have a conversation like that and then we fell asleep. Well, I fell asleep and heard her leave about an hour later. Then I started House of Cards season five and took some PTO the next morning for an unscheduled “doctor’s appointment.” Startup life, man. Unlimited PTO + paralyzing fear of litigation in upper management = any day can be a holiday.

I don’t know if I can keep seeing her. I have some feelings for her, but if I’m gonna be a titan of startup culture I can’t date 20-year-old Chipotle workers forever. She does have 1,200 Instagram followers, but I think I need a 10k-follower minimum kind of chick. Guys who want C-suite lives need C-suite wives.

As for Boca, we’ll see what happens. I think I could find me the right kind of mate in a place like that. They say the women there are as beautiful as the ocean is blue. It also doesn’t hurt that they’re probably loaded and looking to make daddy angry. A man can dream, diary. A man can dream.

For now, I have but one goal: To find my queen. Gil’s stock is on the rise. Tell the people of Boca Raton, FL to hide their daughters and lock up their Bentleys. Hurricane Gil is about to make landfall.

You take it easy, Diary.


Gilbert T. Humplestead

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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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