My Executive Assistant Origin Story

Wednesday, April 21st, is Administrative Professionals Day, where in the United States and a handful of other countries (some of which celebrate on other days of the year), bosses and companies pretend they care by giving their assistants and support staff flowers and chocolates to say “thanks for all of the unpaid emotional labor you do on top of what we actually pay you for, but don’t recognize as ‘hard skills’, so we will never promote you or proactively place you on a career path toward anything else, because you are indispensable and we can’t do anything without you, but we don’t really know what to do with you, so thanks for plating my salad and making my copies and making sure people know I’m not an asshole, even though I am.” It’s like the Mother’s Day or Marriage Anniversary of the office, complete with many of the admins having to remind their bosses the day exists and/or buy their own gifts. It’s also my 24th annual reminder that something has gone horribly awry in my life.

I can actually pinpoint the moment the universe laughed in my face and set me on this path. It was the early 1990’s, and I was in my backyard. It was summer, and my parents were holding one of their traditional summer family bbq’s. My niece had just graduated high school, and I had just finished my second year of college. Someone in my family turned to my niece and asked her if she was going to go to college or get a job. She shyly responded that she was going to get her Associate’s degree at a business school that amongst other things, trains you to be a secretary. My response was immediate, visceral, and condescending. I practically vomited as I spoke, “A secretary — ugh! Why would you ever want to be a secretary? I could never be a secretary!” I had no idea what I would do, but I was certain it was going to be huge and important, and it most definitely would NOT include bringing anyone coffee, which is what I thought was the main job of a secretary at the time.

Fast forward 3 years, and I have finally graduated college after five years with my four-year degree (a Bachelor’s degree in Women’s History and Russian Literature), and a lovely student loan to frame beside it. Again, I had no idea what I was going to do with this degree, but I know I wanted to “change the world”. How to set about doing that was a bit murky, but I began by taking some local unpaid internships while continuing to work as a clerk at my local library as I had during all of my summer and winter breaks throughout college (after having been a page there throughout high school.) My niece, on the other hand, had already begun what would become a highly successful career in Information Technology. It would appear that during her first secretarial gig, something went wrong with her computer, and having gotten some very practical IT education in her business school (and being less fearful than I would ever be), she took the cover off of her CPU tower, and proceeded to fix it. She now lives in Arizona (while making a New York salary) with her husband, many cars and gorgeous dog and hasn’t been a “secretary” since the early 1990’s. (Thanks, universe!)

I, on the other hand, finally got my first “big break” in December 1996. While processing people’s book returns at the library, my former Little League Softball coach came in. He greeted me, and we exchanged some pleasantries, and then he pivoted the conversation to say the following, “Hey, I know you’re into all that Women’s Lib[1] crap… I know someone who used to work at some women’s something-or-other in the New York City Mayor’s Office. If you would like, I can introduce you to her. Maybe she can help you get an internship or whatever. Would you like that?” I rolled my eyes at the “Women’s Lib” part, and quickly said, “Absolutely — I would love that, thank you!” He gave me his contact’s number; she and I connected, and in January 1997, I started an internship at the New York City Commission on the Status of Women in the New York City Mayor’s Office.

In March of 1997, the Executive Director of the Commission called me into her cubicle and offered me a full time, paid position. I was thrilled, until she explained exactly what it would be, “We would like to offer you the position of my assistant. The only catch is you also have to support the Executive Director of the Office of Immigrant Affairs and Language Services, too. I guess since we share an office with them, the administration thinks we should share a secretary, too.” We both laughed, although I didn’t think it was very funny. Not only was I pondering becoming a secretary, but I would have to be a secretary to two people at the same time? But then the Executive Director said the most fateful words ever spoken to me in my twenty-odd years of life at that point, “Oh, and you would also have to move to New York City because you have to be a city resident in order to work here.”

Other than “changing the world”, my single greatest desire at that time was to move out of my parent’s house. Most of my 9 older siblings had moved out only when they had gotten married, and I know my traditional, Catholic mother wanted that to be my fate as well, but I had absolutely no intention of getting married any time soon, nor did I have much more emotional capacity to remain under the same roof as my mother, so I said the following words to the Executive Director, “ This sounds great!” We negotiated a bit over salary, and then I said, “Oh, and I want to be called an Administrative Assistant, not a secretary. I don’t care if it’s official or not. Just refer to me as your Administrative Assistant. It will make me feel better.” She agreed; I signed some paperwork, and I went home that night and told my parents I got a full-time, salaried position with the City of New York with health benefits, and I had 30 days to find an apartment somewhere within the 5 boroughs of New York City, so I would also be moving out. My life was just about to truly begin, and I could not have been more excited.

Fast forward about a year or so, and I started to feel itchy for advancement. I wasn’t crazy about moving to another agency, and there were no growth opportunities within the agencies I was working, so I started looking outside of the government at the plethora of women’s organizations in and around the city. I was sending my resume out for entry-level positions, but I only heard back from two organizations, and they were both for admin positions at or near the same salary I had been making for the past year, and I was beginning to get frustrated. The Executive Director I was working for told me that the investment bank her husband worked at was looking for an Administrative Assistant to support some of the firm’s founders. I scoffed at her suggestion. I was a feminist. There was no way I was ever going to work at an investment bank. I would just keep sending out my resume until I finally landed something somewhere. (Insert second chuckle from universe here.)

Shortly after I rebuffed my Executive Director’s kind offer, she went out on medical leave. I stopped looking for other opportunities to take on a little bit of extra responsibility in the office, as our Associate Director moved up to Interim Director, and our only other agency employee worked part time. An election had also happened, and our previous director decided not to return from medical leave, so a new Executive Director was appointed to our agency, and let’s just say she and I did not work well together. Despite being appointed as the Executive Director of the Commission on the Status of Women, an agency that existed by Charter to provide everything from Small Business Information to Domestic Violence Shelter referrals, and to oversee and assess, in general, how the women of New York City were fairing and advancing, the new Executive Director, amongst other archaic and insulting things, did not think women should be allowed to become fire fighters or police officers. She thought the only true jobs a woman should pursue were nurse (which she had been for decades) or teacher. She too, referred to feminism sarcastically as “Women’s Lib”. The only upside is, because she hated almost everything our office stood for, I got to go to a number of functions as our agency’s representative, thus gaining some great experience and exposure.

Alas, even with the added responsibility, the day-to-day chore of working in an office for a woman who very specifically did not support other women, and whom I had to spend at least 20-straight minutes one day trying to teach how to double-click a mouse (I am not kidding, she would click once and then, instead of clicking again, she would just push the mouse forward on the mousepad… it was the ‘90’s and she was in her 70’s, but she was also making well more than four times my salary, so I just couldn’t take it anymore), I decided it was time for me to go, so I started sending out resumes again.

About that time, our former Executive Director had also called to check in on us and had mentioned to me that her husband’s firm was still looking for an assistant, so I went ahead and reluctantly set up an interview. However, the night before I was scheduled to meet with the office manager there, I decided I wasn’t going to go. It was against everything I stood for, and I truly did not want to go down the path of working for any corporations or banks. I wanted to work for a non-profit that supported women, and I was going to stick to my guns, and I decided I wasn’t going to even show up for that interview the next day. The abusive woman with whom I was living at the time (and that’s definitely a story for another day), quite literally punched me in the arm and yelled, “You don’t get an opportunity like that and not take it!” So, very long story short, I showed up the next day for the interview, but I showed up without my resume and with an attitude that they should “wow” me (ha, was I going to show them!)

Unfortunately for me, they did “wow” me. Turns out, that particular investment bank was full of some of the kindest people I have ever had the pleasure of working with, and some of whom I am still friends with today. They offered me the job. I asked for what I thought was a ludicrous amount of money. They too thought the amount I asked for was ludicrous, but offered me $10,000 less than the ludicrous amount I asked for, which effectively doubled my salary from the Mayor’s Office, which would come in quite handy, as I had that student loan I mentioned, and the aforementioned abusive woman also had convinced me to open numerous store credit cards and max them out to purchase her clothing she needed to try to find a job, so I really needed the higher salary because now I was in a decent amount of credit card debt, as well. So, I gave two weeks’ notice to the anti-feminist director of the Commission on the Status of Women, and went to work at the investment bank I was never going to work at to be the secretary… I mean, Executive Assistant I was never going to be, and 24 years later, I am still an Executive Assistant, although now I work for the President of a women’s organization, so ha! I DID show them. I showed them all!

All attempted humor aside, the above account is my Executive Assistant origin story, albeit the most jaded and bitter version of it. Despite my sarcasm, I am actually incredibly appreciative and grateful for the contacts I had who got me the opportunities that started my career. While I am able to look back on many points of my life where I have made serious and fateful decisions that perhaps led me down a much more difficult path than I would have otherwise liked, and I have endured some very dark, depressing, difficult and demoralizing times as a result of those decisions, I am currently at a place where I can look back without regrets and even have it all make sense and be thankful for my experience and the lessons I have learned.

It is absolutely true that I never wanted to be an Executive Assistant, and despite being truly happy with whom and where I am currently working, I still don’t love being an Executive Assistant, but I am grateful for the skills I have developed and the career I have reluctantly built. I have been truly lucky, blessed and privileged[2] despite my best efforts to otherwise sabotage myself. But having been some version of an “outsider” at every place I have ever worked, I have also been able to see things somewhat differently as an outsider while still being “in it”.

While my opening paragraph is particularly harsh, sarcastic, and based on a lot of stereotypes, I have to believe that it’s also not that far off from what at least some other assistants have experienced. I often feel alone in my thoughts and feelings, but when I separate myself from my insecurities and the visceral emotions driving them, I realize and trust in the fact that I can’t be the only one who thinks and feels the way I do, and thus far, I have yet to have a truly unique experience or thought (although I hopefully express my unoriginal thoughts and experiences in an original and interesting manner).

Yes, there are absolutely healthy work environments — I have worked in many, and not all assistants are female, but I do think we need to look at the fact that 94.6% of administrative professionals are women, and ask how much misogyny and patriarchy have played and continue to play in the history and evolution (or lack thereof) of the secretary, admin and E.A. roles. How much have internalized misogyny and patriarchy led many of us to gratefully take this “behind the scenes” position, where we promote, protect and set our executive up for success every day — most of whom are men, without expecting a traditional career path and job growth trajectory, other than increased responsibility for not necessarily a lot of increase in pay in return (not to mention the unpaid emotional labor I refer to in my first paragraph)?

I am not saying that being an Executive Assistant means I am absolutely perpetuating gender stereotypes, nor am I saying we are helpless victims of patriarchy and misogyny. I am merely asking you all to join me in reexamining office dynamics and how they play out within the social constructs that exist today, and ask, “How did we get here? Do we like it here, and if not, where can we go from here?”

I think Executive Assistants have been and continue to be an invaluable partner and asset to every executive they have successfully supported, and that those executives and their companies owe a tremendous debt of gratitude to their assistant and to all of the other support staff and people in their lives who have done the paid and unpaid physical and emotional labor that allows them to focus almost exclusively on the success of their business. I also think it’s time we assistants and support staff get the recognition for our work that we deserve on a societal level, and not just one day, week or month a year.

[1] For those of you under 40, “Women’s Liberation” or “Women’s Lib”, for short, is often what Second Wave/White Feminism was referred to as in the “mainstream” press for the day and especially by people I was surrounded by who thought feminism was a bunch of hooey, but I digress…

[2] There are many types of privilege I have benefited from and privileges I was afforded and experienced, some of the more obvious I have written about here, but I want to also acknowledge how much white privilege has been a catalyst of my success, although sadly, I have only recently truly learned/begun to understand this. I will write more about how I have specifically benefited from white privilege in another article but did not want it to go entirely unmentioned in this piece.