Thinking · · 3 min read

Fitting into the "boy's club"

Fitting into the "boy's club"
Photo by Timon Studler / Unsplash

In my 20s I started feeling a deep inner conflict about being a woman in a man’s world. I grew up around boys so there’s always been a part of me that’s felt more comfortable around men than women. Because of this, I’ve also always felt that I had to keep up with the boys. So I worked harder, played harder, showed up more aggressively, more loudly…

Then In my early 20s the experience started to shift. I was seen less and less as “one of the boys” and more as an object of desire. So I pivoted and played into that role instead. If you can’t join them, beat them. I leaned into my femininity when it suited me but pulled back to my more “masculine” self when I needed to be assertive.

I’m not going to sit here and deny that women don’t get a certain level of grace in our society—free entry to clubs, free drinks, having doors being opened for you…But these shallow benefits start to lose their value over time. I always end up feeling conflicted whether I should continue to push to be seen as an equal or allow myself to be seen as a “woman” (aka what society deems as someone who needs to be taken care of.) I’m always wondering where I fit in in this very male-driven world.

The reality is I was raised with this conflicting belief. 50% of the time, I was told that finding a husband that’ll take care of me was one of the best things I could do for myself as a woman. In Chinese culture, hearing “don’t do [x] otherwise no husband will want you!” was how we were taught to distinguish between right or wrong actions.

The other 50% of the time, I was told that women need to have the means to take care of themselves. And that as a woman, your safety comes with having your OWN security. Albeit this came later when all the families around me started getting divorced (including my own parents).

I have several core memories of feeling SO out of place in my feminine skin. One of them was the first day I walked into the office for my tech job (a company filled with mostly male developers). The sound of my heeled boots on that linoleum floor still haunts me as I remember the questioning looks. I never wore heels to the office again.

The second time was when I was brought by my CEO to a founders-panel to listen to a talk held by another tech CEO. I was not only the youngest, but the only female there who was not serving the event. Sure, my title at the time showed that I didn’t quite fit in (a marketing manager in a room full of CEOs) but I knew deep down that wasn’t why I felt out of place.

Going back even further, I remember the way my English tutor would act around me. He was a university graduate and I was 15. I could sense the weird power struggle as he was clearly my superior yet it seemed that I could probably get away with anything around him. I distinctly remember him saying to me how attractive I was and that I would be trouble for a lot of men.

The advice we get as women is conflicting as well. Use your femininity to your advantage. Don’t do that, otherwise you’re a slut. Smile and play along and make men feel powerful. Never let a man hold too much power on you. So what’s REALLY the “right” way to act as a woman? Is there ever going to be a version of me that will be respected fully?

Most recently, I’ve been binging Ali Abdaal’s podcast because I’m currently on an entrepreneurial journey and he speaks with quite a few creators and founders that I look up to. But after 30 odd episodes I started to realize that they were all men. Looking into the business books I’ve been reading, the YouTube channels I’ve been following…all of them were created by men. So once again I started thinking about where my place was in this “boys club”.

I’m now working towards bigger goals and dreams than I’ve ever had before. My purpose is becoming clearer and I can’t wait to run in the same circles as the people I’ve admired for years. I know where I want to be, and I’m working on how to get there. But with that comes this innate cognitive dissonance around whether to keep showing up as my “masculine” self or to finally let go and feel like my divine feminine.

Can women succeed in the business world even when they want to tap into their femininity?

This is not an article where I give you the answers. This is just me looking to figure it out.

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