Don't Wear White Shoes With An All Black Outfit

How a comment changed my behavior but also, how this type of reaction made me good at being an EA

I realized something about myself. Most of the memories I have in life exist because I was embarrassed in that very moment - whether I embarrassed myself by doing or saying something or someone made me feel that way by doing or saying something.

I get into this self-talk mode of “omg, that was so embarrassing, Janet, please don’t ever say or do that thing ever again!” And that would shape my personality over time.

I went on a date in 2006 (eek so long ago). It was a first date. Dinner was good. Osha Thai in SF when it was hot and hip. Had a couple drinks after. But, long story short, there was no chemistry, and I think it was evident for both of us, which was fine, we stayed friends-ish after.

When he dropped me off, he got out of the car to walk me to the front door. Aww how sweet. Chivalry at its finest.

But then he said something that made me feel embarrassed. “You look great tonight, but in the future, don’t wear white shoes with an all black outfit. You’re not supposed to.”

Speechless and confused and with a nervous chuckle (because I didn’t know how to respond to that, I mean how DO you?), I bid my adieu and went home. And I questioned everything about my outfit choices. I was already insecure about what I wore on the daily (this has been a thing most of my life), but his comment solidified my insecurities. I was officially fashion dumb. What other “rules” do I not know of? How did I never hear about this?

First of all (and I wish I had this thinking back then), clearly I was living in the future. Because all I see nowadays is everyone in all black outfits with white shoes. That’s like the quintessential, SF Bay Area, Tech Designer uniform. And such a classic, monochrome, covid 2020 quarantine outfit. Either way, I am convinced that I was cool back then (my kids will think otherwise), ahead of the fashion game if you will. HA!

Secondly, until recently, like in the last 5 years, I never wore an all black outfit with white shoes EVER again after that. And even today, if I happen to be wearing that (I’m actually wearing that now as I write this which is what spawned this post), I am reminded of what this person said about my fashion choice.

This personality and behavior shift is typical of me though (is it childhood trauma?). It’s not so much what he said to me, it’s more that I grew up hearing something and believing it and altering the way I behaved, like in this situation. This behavior, though, is what contributed to me being a good assistant early in my career and what made me end up loving the role lol.

Essentially, I know how to follow directions really well and do what is asked of me, and I don’t break the rules. (Yep, it’s def childhood trauma)

At the start of an Administrative Assistant career, those types of skills will help. You’re new to the role, you’re figuring things out, you’re learning your executive. If your executive says they like their calendar a certain way, you listen. If they tell you not to do something, you listen. If they tell you what hotel and airline they like, you listen.

It’s helpful to many executives to simply do as you’re asked and get shit done. Just say ok and “don’t wear those white shoes with your all black outfit next time”.

Once you get the hang of the role, you’re able to be proactive and anticipate the needs of your executives. Also, with all the mistakes you’ve made that you learned from, and your own life and work experiences, and the years that go by, you get better at being an assistant and work your way up to more responsibilities and supporting higher executives. At which point, “you end up wearing whatever you want however way you want to”.

When I think of Janet in her mid 20s, I am a little sad for her. For lacking the confidence, for letting others shape how she behaves, for allowing a comment change how she dresses, and for not having a strong backbone.

But I’m also happy for her because it is for those reasons she learned to become a better EA for so many people. It is for those reasons she learned to observe her executives’ patterns and behaviors and listen to their needs. It is for those reasons she learned how to adapt to so many different people. It is for those reasons she gained confidence over the years and learned to grow that backbone.

Perhaps the lack of confidence and insecurities were required at that moment in life. They needed to be there to shape who I would become later and to keep me humble. But I think that’s life anyway, right? We learn from our past and build on it. And because of that, who we are today ends up being very different than who we were 20 years ago.