What is cool anyway?
Maybe I am finally cool, for the first time in my life. Despite what randoms say in my DMs.
What does it mean to be cool? I have been thinking about this since I got this DM today from a stranger who claims to have met me once.
Google would tell me that “cool” is about having a sense of self-assuredness without arrogance. I never had this really. Well, I had the “without arrogance” but not the “self-assuredness.” Not until recently, in my 50s!
In high school, I was such a dork. I was scrawny. I had no friends. I sat alone at lunch. And didn’t eat (anorexic). I switched high schools 3 times. It’s hard to make friends when you’re always moving schools. It’s hard to be cool if you have no friends.
I moved schools because of gymnastics.
I switched gyms (and towns) after my freshman year. Then I went to a small private high school with only about 8 kids in my class, in Allentown, when I switched gyms mid-way through my sophomore year. I went there so I could leave at will to go to practice.
And then I switched to a Catholic school my junior year so that I could have a semi-normal high school experience despite training 8 hours a day. It says something when “semi-normal” means going to a Catholic school as a Jewish girl and leaving at 12:30 every day to fit in all the training. That was semi-normal compared to the prior 8-kids-in-a-class experience. But there was nothing normal about it.
One month into my junior year at a new school, I was out for a month for training camp for World Championships, and then travel to Montreal for World Championships. At that competition I broke my femur on my last event. I was in a full leg cast by the time I came home. And very depressed. So I missed another month of school. Semi-normal it was not.
I was awkward and weird and pre-pubescent at 16 and never got invited anywhere because I was quiet, and painfully shy, and I was at the gym all the time.
I was most definitely not cool.
When I went to college, I had just quit gymnastics and felt like a total failure despite my successes. I was on crutches, having just had my first ankle surgery. I was socially immature. And I gained about 30 pounds after eating a sandwich, post many years of a 400-calorie-a-day starvation diet. Chubby, gimpy and depressed is most definitely not cool.
I got a little cool in college after that freshman year. I was — well, I guess you’d call it kind of goth. Over-dyed black hair. Sometimes platinum. Thrift store chic, smelly overcoats and used graphic t-shirts. I hung out with the rejects. The skaters and druggies and hippies and gays who were still outsiders in the 80s. We were mad at the world and oh so Gen X. We had little in common except being mad at everyone and everything. I got my first tattoo. I pierced my nose before that was ubiquitous. I marched against war and for taking back the night. I hated sororities and blonde girls and cheer leaders. If for no other reason than they seemed to take the easy route to being liked. I made it hard to like me. You really had to work at it.
I graduated and I was still mad at the world and still kind of chubby. I had terrible hair and eyebrows. I made no money. I worked odd jobs — remember temping? — and I scoped out all the happy hours that had free hot dogs to feed myself.
Then I got tired of having no money and I took a job at an ad agency. It seemed corporate and very uncool to me — I wanted to be a writer or a filmmaker but lacked the courage. I liked the job though and I moved up. I did it by keeping my head down and doing the work. I wasn’t flashy. I didn’t push for promotions. I just did the work.
I was straddling two worlds. My creative friends were writing novels and screenplays with little success but had cool bona fides. And I had friends that took jobs at places like McKinsey and made real money (80K out of college!) and nice apartments and real relationships rather than hook ups at dive bars.
Either ends of that spectrum felt decidedly more cool than me, in the mushy middle just trying to get by.
At 25, I met my first husband. Or he would become that in 5 years. That was cool. He was tall and odd and smart. And black, which upped the cool ante if we’re being honest, but that wasn’t why I liked him because that would be gross and weird. He was nerdy like me and it worked. Until it didn’t.
I was the first of any of my friends to have kids. Not cool. They were still going out to raves and I was home nursing and working my job — which by that time was an actual corporate job at Levi’s. I was a low level marketing manager. “Middle-manager” is not the coolest. I managed budget spreadsheets and took orders and went to places like Menomonee Falls, Wisconsin, the home of Kohls, to meet with mid-level “buyers” in bad, ill-fitting suits (them, not me), in dingy conference rooms with terrible coffee in styrofoam cups (when those were still a thing).
But sometime in my mid-30s, I got more confident. I did the job my way. I wasn’t cut throat. I tried to help the people who worked for me to build meaningful careers. I wasn’t chubby anymore. I didn’t feel ashamed of having a corporate job. I wore jeans everywhere, even formal events, because hey, I was a reasonably high level Levi’s exec.
By my early 40s, I was kinda cool, I’ll admit. To the outside world, anyway. I led the Levi’s marketing organization. I made deals, myself, with celebs including Justin Timberlake, Alicia Keys, Snoop Dogg and Tyler the Creator. We hosted private concerts with Lauryn Hill and Chance the Rapper and I was the VIP in the green room backstage. They respected the title, not me, and I knew that. But I was nice, and honest in my dealings which I think was kind of refreshing for them. I went to Coachella and Flog Gnaw and had my own seats at Levi’s Stadium.
But I didn’t feel cool. I know I probably appeared to be at my apex of coolness to the outside world. To people like Ariel of the DM above. But my first marriage had ended. Divorce isn’t cool and felt pretty shameful to me, at the time. I was running myself ragged trying to work and take care of my two tween boys.
I still tried to create a work environment that allowed my teammates to flourish. And I liked that. But I held my tongue. A lot. I didn’t always say what I thought. Ironically, Ariel probably met me during that time and thinks that’s when I was cool. But I wasn’t. I might have appeared to be but I was stuck. I needed the job. I was lonely. And I was very tired.
In March 2020, the madness of the world unleashed me. I could no longer hold my tongue. I risked everything I’d worked for. Not because I thought it was cool. But because I thought it mattered. I thought kids mattered, and truth mattered. And so, sometime around the age of 51, married for a second time with two more kids and no longer lonely or wanting or wishing, maybe I actually became “cool.” If cool means self-assuredness without arrogance, that was definitely me during the covid era.
Another definition of cool might be not easily flustered or upset, maintaining composure under pressure. I definitely did that. I was composed despite the mob coming for me. My husband helped in that regard. I held fast to my values. Truth seeking. Freedom of speech. Standing up for the vulnerable.
And now, I have my start-up. Which the world thinks is pretty cool — especially if you’re a woman — but not if you’re viewed as “conservative.” Which I’m not but the world — by that I mean mainstream media and psychos on Twitter/X — views me as such. Because if you don’t think Elon did the Nazi salute you’re a conservative now.
But I honestly feel cooler now at 55 than I ever have in my life. Because I don’t give a fuck what anyone thinks of me.
Not caring what Ariel says about me is kinda cool.
Not caring when journalists post tweets (attached to headlines) — inferring I’m a Nazi AND a racist — is kinda cool.
Criticizing the government used to be cool. I’d argue it still is. And that Democrats who were used to having the corner on cool are the committed conformists now, which is so UNCOOL.
A big criticism from the loonie left is that I went beyond calling for open schools during lockdowns and I criticized government officials! Oh no! The horror!
Not giving a fuck is definitely cool. It’s kind of the classic definition, isn’t it?
Thinking being cool actually matters is so uncool. Because thinking being cool matters means you are trying to fit in with some culturally approved aesthetic. Which I am most definitely not doing.
So Ariel, conformist Ariel, repeating Democratic Party issued talking points about masking and the oh so many sexes there are and “misinformation” and Elon being a Nazi — I think you are in fact the very uncool one.
But thank you for the feedback.
Side note: Thank you all for reading my random musings. I don’t have a ton of followers but I look forward to your comments and your emails and DMs. And I enjoy having a place for random musings that people, however few, like reading! So thank you!
Well, I for one am here cuz I heard you interviewed on a podcast at some point in the past year and I thought “This Sey woman is a badass and I want to hear more from her!” Speaking truth to power is the bravest form of cool😎
We learn as we mature, Jenn. Each of us follow a path that lead to doors that open for our future growth and stability.
For me, cool never mattered. Actions, not words. You are an action leader. Keep up the good work. Keep walking through those doors.