educated donkey (smart ass)

Oh, the things I get away with.

I’m pretty sure my boss is convinced I’m a smartass. I’m one step ahead. I know I’m a smartass. You know how? My 8th grade teacher told me so, except he called me an “educated donkey” because he wasn’t allowed to call a student a smartass outright. I’ve lived up to the name ever since.

Although he’d never give me the satisfaction of hearing him admit it, I know that my boss secretly enjoys my “smartass-ery.” Our relationship has evolved from one of oblivious intern/busy CEO (when I interned for him in college), to rookie executive assistant learning the ropes/flustered CEO who went through 3 assistants in the last year (when I got hired last year), to seasoned assistant who is on top of everything/impressed CEO with more time on his hands (when I recently mastered all my duties and then some), to cheeky, happy-go-lucky girl who is hungry most of the time/guy who just wants to go home and nap (now).

To put it pictorially, in October, when I first started, we were professional and polite:

And now…

Boss: Where are you off to?
Lily: The post office. Then a quick lunch.
Boss: But [the client] is going to call you to give us his payment information. (Smiling) It’s for a lot of money.
Lily: (Returning the smile) Oh, but I’m going to call him back because I’m hungry and need sustenance! (Walks away)

Boss: Lily, do you think this folder is okay to carry around?
Lily: Why, what’s wrong with it?
Boss: It’s got some scratches on this side.
Lily: Let me see that. (inspects scratches, flips the folder over) Just carry it this way!
Boss: I’m glad you’re here to solve the bigger problems of this business.

(end of the work day on Friday, Boss strolls into my office)
Boss: You know, this one time when I was little, I —
Lily: Can’t you see I’m working?!

Boss: I’m about to hop on the phone with [our client]. His last assistant died, you know.
Lily: Really?
Boss: Consider that a warning. (walks aways slowly)

Boss: I really appreciate you staying later, Lily. I’m very touched that you care so much about the business.
Lily: No problem, Boss!
Boss: Here, take this grapefruit.
Lily: Um, it’s okay.
Boss: Don’t worry about it. I’ve got two.

Yesterday, my boss told me that I could work from home today. If you haven’t experienced working from home before, let me tell you that it is glorious. Working from home is like an early weekend. Working from home means keeping an eye on e-mails coming in, setting up an “out-of-office” automated message for cruise control, and staying in your pajamas. Working from home is freedom!

…So you can imagine my disappointment when he called late last night to tell me that I was, indeed, to face traffic in the morning and head down to the office for something that required my attention. I responded, “I better be getting another grapefruit out of this.”

This morning, upon entering my office, I found a grapefruit sitting on my computer.