Too Awkward to Fail: My First Week as an Accidental CEO

On January 1st, I became CEO of my company. This is not because I am a power-hungry stony bitch who wears a lot of pencil skirts and is determined to claw her way to the top of the corporate ladder, nor am I a hip, young engineer, with a pool table and tap beer in my office, who has figured out a way to make apps greener or something. I became the CEO pretty much for being in the wrong place at the wrong time.

I’ve never been an overly ambitious person (ambitious people have to network). I’d always thought I’d end up a jaded lit professor at some mid-tier private college who spouted worldly wisdom in a 60-year-old-chainsmoker voice and gave everyone As because what does it even mean anyway. But I’ve always somehow ended up being in charge at nearly every job I’ve ever worked. This is because a) I cannot physically function without a system in place. I need to know when and where and how things are going to happen. Surprises are for extroverts. Give me schedules and reassurance! And b) I am very, very bad at saying no, especially to work, because I am too stubborn to admit that I am lazy.

To make a very long story short, my company was acquired by a much larger company as of January 1st. The acquisition was nearly an 18-month-long process filled with renegotiations, disputes, and a bit of grown men crying, but when it was all said and done, the new owner came to find he did not want the ex-owner (my boss) in charge. Then he met with me and asked me a question about finances, and I said something ingeniously along the lines of you-shouldn’t-spend-more-money-than-you-have, and badda bing…due to the age-old mixture of logic and spite, I was CEO.

I was technically asked but didn’t really have too much of a choice, and the position came with a bit more money, and I have essentially been living off of peanut butter and pretzels. So here I am, a CEO, and I feel really obnoxious about it. And after one week on the job, I can officially say I have no idea what a CEO does.

It’s true. I tried googling it and everything. I don’t really know what the nature of my job is. I just know Bernie Sanders hates me.

But like a true American, I suppose I’ll have to figure it out as I go.

Here are some of my observations based on my experiences of the last few work days…

  • CEOs delegate: I decide what gets done and when it gets done. This is actually something I can do. Time management is one of my two skills (that and rapping, obviously). The challenge here is being assertive enough to tell people to do something, and to occasionally do it faster and better than they are willing to. On top of that, I do not want to come across like an asshole. I do not like assholes. The people or the things (seriously, who came up with those anyway?). Thus far, this has resulted in a lot of stammering and confused sentences.
  • CEOs solve problems: Heat broken in the office? Either I talk to maintenance or everyone freezes. Freeze, it is! (Just kidding, I talked to them, but I did not like it one bit!)
  • CEOs make decisions: Keurig or coffee pot? Excuse me while I deliberate with myself for 3 hours.
  • CEOs talk on the phone: And evidently, it is often about things I know nothing about, like professional liability insurance, interest rates, and profit margins. My only hope is that I can confuse them with big words like “synergy” and saying things like “correct” instead of “yeah.” Still have yet to uncover the appropriateness of “okey dokey.”
  • CEOs sign checks: Which either makes me the most popular or most hated person in the room. I’ve always been too apathetic to be either, so this’ll be interesting.
  • CEOs look at spreadsheets: At this point, I’m just nodding a lot.
  • CEOs are the face of the company: Hope you like masks!
  • CEOs wear professional outfits: So I guess it’s time I learn how to walk in heels and if I’m an autumn or a summer. I still don’t understand a lot about fashion, and I especially don’t understand why I must get dressed up to sit in a cubicle. My computer has seen me at my best and worst and loves me just the same. I also could never get behind the “look good, feel good” mentality. Ya know when I feel good? When I get the extra fifteen minutes of sleep. But I am a CEO now, and so may my eyes be lined, may my blazer be pressed, may my pants be trousers, may my mirror be sturdy.

Clearly, I am currently faking it. Right now, I am sitting at my computer typing this with a furrowed brow and look of determination so my staff will think I am up to things of utmost importance. I really miss being an editor when I just got to read stories all day and nobody’s livelihood was in my hands. But I will not fail. I will climb the ladder very carefully in the hopes that I do not slip and fall in my insensible shoes.

That is not because I crave success. It is because I really don’t like it when people yell at me.


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