Great Executive Assistants are made, not born
My journey from ridesharing to Executive Assistant for Ueno’s CEO
Fortune doesn’t always favor the prepared: I write this as an executive assistant to a CEO at a hot shot design agency; a position I did not aspire to nor one I am naturally suited for. But history is not made by those who were born to be great heroes (or executive assistants), but those who become heroes (or great executive assistants), after Destiny calls.
In 2013, San Francisco suffered from a nasty case of entrepreneurial activity mimicking the dot-com-y ’90s. One could barely do an honest load of laundry at the corner laundromat without someone suggesting how passé the activity was, now that there was an app for that.
Always an early adopter, I figured I would look to participate in the new economy from the ground up. The numbingly boring print production gig that was paying my bills for the past 10 years was finally drying out with the Death Of Print, so I figured I would try out what everyone was talking about: the ridesharing service called Lyft. Just to fill in between the real work. Or so I thought.
I didn’t particularly like driving, and I was not exceptionally great with directions, but I just like being in my car, moving or parked. I always feel at home in the car. I don’t believe in car culture, but I am Car Culture.
I was hooked right away. It turned out to be the perfect job for the pathologically extroverted. And while I knew I really needed to look for a real job, driving was a perfect instrument of procrastination that kept me in the money but away from getting serious about updating my skills and getting a resume out. I didn’t realize how isolated I was after working from home for 10 years. Not everyone wants to talk to the driver, but a good portion of people do, so soon I was doing more small talk than the girl with the keg tap at a frat party. The drawback was that not since being young, cute, and heavily-accented did I have so much insipid conversations about where I was from.
And while I am generally outgoing, I do suffer phobia of being trapped in repeat, boring conversation with no escape. But in the car, almost anyone can be interesting for ten minutes — the art is how to break into the enticing stuff on a short timeline — and if one fails, it is over soon enough.
I had a jolly good time of it for about three years — resulting in my now famous blog, alsosanfrancisco.com — when an opportunity to drive for a wheelchair-accessible Uber service presented itself. At that point my lower back had already gone on a bit of a strike, so upgrading to a larger and therefore more comfortable vehicle seemed like a good idea. Additionally, since I was getting grief from my left-of-center buddies about stealing jobs from the cabbies, driving wheelchair accessible van seemed like a good way to redeem myself.
The gig turned out to be life-changing in more than one way. During that year, I met many incredible people and heard about almost every crazy tragic accident that can land one in a wheelchair. (If you think accounting is a physically risk-free career choice, think again.) Almost all of my passengers were regulars with whom I made friends. And they were all great.
…Except for the silent man in black I kept picking up in Tenderloin. The first time I drove him was nearly the first time I drove the van and, as I was strapping his wheelchair in (somewhat trickier than it looks for a newbie), he followed my every move with a judgy eye, completely resistant to my world-class small talk skills. To my dismay, I started driving him on daily basis, during which barely audible greetings were exchanged. I just assumed he was somewhere on the spectrum, or differently-abled intellectually in some other way. This was not a surprise since many passengers I picked up near the shelter on that block were unusual — and one can easily end up being unusual just from living at a shelter.
Here I would like to point out to the naysayers that I fully respect not everyone is obliged to chat up their Lyft or Uber driver. They indeed are not, so after a smile and a nod, feel free to retreat to your vault of thought or whatever you have going on your smartphone. There are enough people oversharing that even the chattiest of the drivers get their fill. What I am talking about with this passenger here is a whole new level of glum silence on a daily basis. Never had I interacted with someone this often in a small shared space without exchanging any niceties.
About four months went by in nearly complete silence, and Haraldur, the name on the Uber account of this silent man in black, became a bit of a fixture in all my conversations with friends. Everybody wanted to know if I was making any progress in finding out about his clearly made-up name and peculiar nature.
Therefore it was a bit of a revelation when during one ride his phone rang, he answered, and proceeded to discuss details of some complex business deal. He sounded perfectly articulate and even more surprisingly, somewhat insightful and really kind of chatty. There was only one conclusion to be drawn — that he was an elitist moron who would not bother to make small-talk to someone below his station, such as Uber driver.
“Well fuck it,” I thought, “see if I care,” and I started listening to obscure audio books, something to which I usually don’t subject my passengers.
As a driver, there are destinations I prefer, some I am indifferent to, and some I loathe. Silicon Valley leads my hate list. It’s not pretty and it’s not fun, especially in the wheelchair accessible van where the suspension is reinforced to the point that the van handles like a tank. A tank maneuvering on the six lanes of Tesla-infested 101.
So when my passenger expressed the need to go to Menlo Park for the second time in one week, something inside me broke. I turned around and spoke my truth. I think I started with “you listen to me,” — an opener that rarely leads to consensus building.
As I watched him taking it in, I was not getting any satisfaction from his bemused expression. In fact, he looked as entertained as I had ever seen him, which is not to say much, but the corner of his mouth did quiver in a slightly upward motion. When I brought up that I had thought he was elitist, he responded “I heard that one before” with some glee, even pride. I was rather impressed he was taking it so well.
This exchange resulted in a truce which led to him occasionally saying a few words, clearly just for my benefit, not any actual need for talk, but I relaxed enough to go ahead and carry on a conversation (even if mostly talking to myself). Talking is the way my brain forms thoughts, thoughts that don’t get to be fully-baked unless there is a semi-conscious audience. I would occasionally throw a control question in, and overwhelmingly The Haraldur would claim that the back of the van was too loud to hear. I know this to be true, to a point. Hearing a normal-voiced speaker when on the freeway is rather difficult in a shaking van, but not someone whose resting voice level is above 80 decibels, like yours truly.
Haraldur would occasionally comment on the radio programming or the book I was listening to quietly in the front, proving thus he was hearing at least some of it, and his comments, no surprise, were generally in the negative. The post Trump-election months were a disappointment to both of us, but he was also quite down on cultural pop icons such as Shakespeare, Spinoza and the like. Turns out they were all overrated lightweights, according to Haraldur. There was one philosopher he did comment on positively, but I no longer remember who it was. Someone depressing, I am pretty sure.
This time period was painful for both of us, as he told me later. As eager I was to arrive at the revelry of shared human experience, he was just as eager to stay in the comfort zone of awkward silences. I, apparently, have no empathy for introverts, he said. Which is not true — I have so much empathy for introverts that I cannot wait to talk to them about it.
A few times I picked up Haraldur with other people who worked for the company. They all seem a perfectly normal and affable bunch of millennials with whom I had a good rapport, and who, even more surprisingly, seemed to appreciate my passenger just fine. One exceptionally friendly individual told me upon exiting “I can now see how Halli and you would like each other.”
“Who is Halli”, I thought, and, “like each other”? What an incredibly cryptic remark, since there was no way the negatively-inclined man in black went by the cuddly name of Halli, and there was definitely no liking in progress on either side.
Fast forward a few months, and Haraldur and I had made small but significant progress in communication. I met his fantastic wife and adorable children, drove him to many more destinations, and had many more awkward conversations frustrating to both of us. But nothing prepared me for his text on one fateful Sunday in which he asked me if I wanted to be his executive assistant.
To say that I was taken aback by the offer would be an understatement. I had a vague idea that the job was basically administrative, and therefore wouldn’t one need to be able to type, spell, take a dictation, organize a calendar, etc.?These are more or less all the skills that I had so far managed to avoid. I am not a computer illiterate when it comes to Photoshop, Illustrator and the like, but my organizational method stems more from my background of an abstract expressionist painter than from engineering, despite having also studied the latter in my misguided youth. Though one could argue there is an underlying organizational system to abstract expressionism, albeit one very difficult to detect.
The only 9–5 jobs I ever had were in the large production departments, where the administratives over at management were viewed as the unimaginative killjoys with spreadsheets and zero understanding of how the real work gets done. Would I dare to breach the divide? Is this something I could actually do? What would happen to my humanity? I clearly needed to get over myself and grab that opportunity to work at a hot shot agency with a real paycheck and benefits and maybe learn something new in the process. (Including about myself). I have kids, for Christ’s sake.
I did try to inquire what being an executive assistant actually entails, but my future boss rebuffed my inquiry with “I have no idea, I never had one.” And then he said he based my aptitude for the job on the fact that I am always on time. Which is a fact. I am propelled by Eastern European brand of anxiety to expect all sorts of stumbling blocks between the task at hand and the road to completion. I don’t think I was late a single time I came to pick him up.
I then had to endure a week of interviews with an alarmed group of Uenies who were put into the uncomfortable position of having to hire the boss’s Uber driver for a job that many perfectly qualified professional EAs applied for. Haraldur didn’t like any of them, since they were all little too perfect, I am sure.
Even worse than all the interviews was getting hired. I received the email notification while stuck in a bad traffic on the Embarcadero with a tourist family from somewhere in South America who spoke minimal English. They did their absolute best to share my enthusiasm and anxiety while having very little understanding what all the hair pulling was about. (I did get them safely to their destination, but they are probably going to remember that ride for a long time.)
There was about a month long gap between me getting hired and me starting the job. This in-between time resembled sitting in the dentist’s waiting room waiting for a wisdom tooth extraction — back in the old country where the procedure didn’t involve any anesthesia.
Starting the job was considerably more pleasant than the hiring process. This was thanks to incredible competence of Najla, the onboarding professional, whose job is to put people at ease post-Haraldur-interview experience, and who made a point of praising my exceptional intelligence, personality and wit to such excess it almost started to sound credible to my BS-untrained ear. (Sure, she does this with everyone, but when basking in the light of her attention anything seems truly possible.)
I wasn’t sure how long it would take me to fail at this job which consists of all the things I am bad at, and didn’t require any of the things that I am good at, but right now I am six mind-expanding months into it. After all, Google calendar only has about five features to master, that is, five features that are not immediately obvious to one who has already booked many a cupcake fundraiser for the PTO.
My buddy Karli here at Ueno keeps telling me that I will not be an effective EA till I believe myself to be one, which is the most American thing an American can say, and when applied to her case perfectly actionable (a word she actually uses), but not because this is any kind of truism that applies to most people. Nevertheless, I am getting better at this, and if I really focus I can book a perfectly good video chat (we use Zoom, is that good for you?) across several time zones.
The greatest learning curve for me was the understanding of the business side of things — and let’s just say the suspicion I had about management pulling random deadlines out of a hat just to aggravate production were confirmed. Haha, just kidding. The business development people here at Ueno do a great job, and so does my amazing boss, can I please keep working here? There is still so much to learn, but it also seems much more manageable than it was 6 months ago.
I still drive the company van whenever this is needed, and my communication with the Haraldur is pretty much the same it ever was — that is, I talk and he doesn’t listen. But there are also free lunches, a creative environment, many delightful humans, and the paychecks keep coming. So what can possibly go wrong?
Note from Haraldur on this “article”: None of this is true. I am a perfectly nice person. Let’s discuss in our next 1:1 / exit interview.
Lutzka is Ueno CEO’s Executive Assistant based in San Francisco. Want to work with Lutzka? Come work at Ueno.
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