Hopper office-at-night
“Office At Night” Edward Hopper, 1940 Oil on Canvas

My Darling Boss,

I’m sorry to tell you via email, but I am resigning as your assistant. I’m sorry it couldn’t wait until you returned, but I want to give HR enough time before I leave to find someone more suitable.

You will roll your eyes and say that I’m privileged, that I’ve never had to work hard or pay attention. It is mostly true: I’ve never had to work hard for anything, but I have been paying attention. I know the difference between working hard at something you are suitable for and trying to adapt yourself to a position that doesn’t utilize your strengths or tap your interests.
You have been a patient and forgiving boss, but I am not a good assistant. Instead, as you like to say, it’s often the other way around. A few weeks ago you said you wanted to see me fail, and I was surprised because I already felt like I was failing a little every day. There is still plenty I don’t understand about you, but you would never fire me because it is not in your nature. You don’t like to say no.
I see your relationships with people you like but don’t find competent. You let them walk away or someone else lets them go – Executive X resigned long after you told me you were disappointed in his performance. Unlike Executive X however, I don’t have anything else tugging at my attention. The bottom line is someone else can do this job much better than I can.
I don’t flatter myself to think I put a damper on your trip, but I hope you enjoy the rest of your vacation. I’m still here.
Thank you,

Your assistant

I wasn’t trying to be cruel, in fact just the opposite. I had wanted to wait until my boss returned from vacation to break the news to him. Having never been in a relationship, I’ve never had to break up with anyone – I won’t venture to say it’s the same thing, but to all the heartbreakers out there, the dread you feel, especially when you know the other party, despite their constant nagging and eye-rolling, is on some level quite fond of you – the dread is similar, no?

Then there is break-up etiquette. We’ve all been schooled by our media girlfriend’s horror stories of some asshole breaking up with them over text message or email (though nowadays email is seen more and more as “well, at least he emailed you”) and who can forget Carol Bartz’s firing from Yahoo? No one was firing me, but leaving a workplace – especially a cherished one, where you treasure the relationships you have with your coworkers (my darling boss included), is something to be handled with care.

I wanted to walk into my boss’s office, he unsuspecting (or least I hope so – dread smells different from fear), and say as steadily as possible:

“Boss, I need to talk to you about something.”

I might have lost it and started crying and apologized profusely while saying all the wrong things, but at least my boss would have seen my expressions and known that the decision had not been easy. I had struggled. After all, I had accepted the position thinking that I would stay for at least a year and a half, and as time wore on, slowly whittled it down to a year and three months and finally to a year, though in truth I will barely make it. (My first day was August 8th of last year).

Even though my heart would have immediately been ten thousand times lighter as soon as he knew, it still hurt because between us on the table – a gorgeous black leather desk I had been so impressed by when we met for the first time as boss and future assistant – on the table was a good relationship.

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