“It’s Simple.” This Is Why I’m Not the CEO (Or Someone Thereabouts)

organized desk.jpeg

Early in my short-lived career as an Executive Assistant (which is to say, about two weeks into a year), I was routinely flabbergasted by how clear my boss had everything in his head.

“Well, he’s the CEO,” my dad would say, “You think he got there by being confused all the time?” 

True, he was the CEO, but he also human like me, no? How could it be that a man could glance at a sheet of numbers or a webpage full of flight times and know immediately what was going on without a second read? How could it be that he could meet someone, remember their name, title, and what it was their business was?

I remember more than once spending hours putting together documents for him, spell-checking everything and doing the math and getting at least two other people in the company to look things over before I sent it to him. He would take it and peer at it with his usual expression, an impossible mix of impatience and deep concentration, then toss it back at me, “Where’s X?” or “You’ve left out X,” or “How you have Z here, it doesn’t make sense.” X, Y and Z always being not crazy vital information but information necessary to do the job right. Or sometimes, vital information.

He would often try, to his credit, to take the time to sit with me and explain how something worked or exactly how he needed his itinerary to be, but for whatever reason, out of overthinking or just not thinking, I would sit there with a dull expression on my face and he would say, “You don’t understand? But it’s so simple.”

And he would take a marker and draw a diagram for me.

“I’m here now, right?”


“And on Tuesday, I need to go here, right?”


“But I don’t want to spend the night here, because I need to be here, at this time, right?”


“So I want you to find the best times for me to go from here to here to here and then back to here, with the least number of connections and less than two hours for each connection, otherwise, because of the time change, I’m going to miss the meeting back here on Thursday, right?”

The CEO of what was then a billion dollar company, drawing on his standing notepad – the kind meant for grand business ideas and effective marketing strategies – trying to illustrate to me how to book his flights.

After a few minutes of this (and I’m not too proud to say this happened more than a few times) he would sigh, out of weariness rather than kindness, and say, “Call Florence (our travel agent) and bring the phone to me, I’ll talk to her myself.”

And in this way he was often doing the job I was meant to do for him.

I gave my boss the first month for me to be impressed by him – though looking back, it was he who gave me an entire year to bow out and admit that I wasn’t cut out to do an organized person’s job.

Not that I wasn’t organized – by any friend or family member’s measure I was superficially the most organized person many of them knew. My room was always neat as a pin, with socks and underwear folded into shoe boxes in my dresser, clothes hanging by length within their respective categories, sweaters rolled, shoes cleaned and lined up at the foot of everything. Bookshelves – which in more recent year have, thanks to Tom, undergone the new and more obvious categorization alphabetical order within genre – were in those days divided into Non Fiction by category (travel, food, health, money – my four, undying obsessions), and Fiction – classics and contemporary fiction, which I arranged by putting whatever spines looked prettiest alongside others. My room, my penmanship, the careful way I logged dates in my agenda and never forgot a meeting with friends and was in general excellent at the daily upkeep of chores: laundry, car maintenance, throwing old things out – it all pointed to a promising career in Administration.

Except as we all know by now, appearances – like people who interview well – can be deceiving.

One evening many years ago, my aunt questioned me about my apparent compulsion to organize. I was fourteen or so. She sat in my room watching me rearrange my bookshelf to make room for some new books I’d bought earlier that day. Books I would never read them but would always proudly display. Like I said: appearances, appearances.

“Why do you keep things like this? What… – she searched for the English word while marveling at my apparent dedication to the task – “…motivates you to be so organized?”

At the time I didn’t have a stock answer prepared, but I sat amidst a pile of books, knowing that I would not be able to sleep until each was in its place. I considered her question.

For a fourteen year old, it was a sudden, simple strike of clarity, one that didn’t and still doesn’t happen very often.

“I always feel very messy inside,” I said, “Disorganized and foggy-brained. This helps me feel like I’m in control.”

Further inquiry would have revealed that I was also borderline obsessive compulsive and, like most of my classmates, a champion at procrastination. Paper to write? Looks like a great opportunity to rearrange my desk. Test to study for? I think it’s time to go through my closet and donate all the items I no longer wear. Dad wants help in the garage? Sorry, I’m refolding all my socks.

Cleaning, organizing, making things just so – these were, before boys and drugs and alcohol (and even now after all those things), a huge source of enjoyment and accomplishment, however fleeting.


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