Too Pretty to Be Successful?

What happened?

Last summer I earned an internship at a growing tech startup in New York City. The company had reached a significant valuation—you might not even call it a startup anymore. To welcome the new intern class, the company held a nighttime party on a yacht during the first week of the internship. It was an upscale affair, for a startup at least, and so people dressed up.

It was at that party that I first met my boss. He was incredibly drunk. I was nervous because I wanted to make a good impression on him, but I held my own, was confident, as was definitely sure not to get drunk. 

At one point during our initial interaction, we chatted in a circle of 5 individuals: My boss, myself, and three other employees—two of whom were women. My boss began telling us about why he was so motivated in his work. He said that one of the main reasons was because of his ex-girlfriend from high school. He went on to explain that she was one of the first people to tell him that he had a lot of potential, but he really needed to apply himself in order to achieve anything. Someone in the circle asked what she was doing now. My boss, without hesitation, replied, “Oh, she was way too pretty to become successful.”

How did you respond?

I was absolutely shocked. My boss elaborated: “She was the hottest girl in school. She was way too pretty to actually be successful.” To make matters worse, he was making direct eye contact with me while he said all of these things, which made me feel like he was speaking directly to me. 

I instantly began to question what he was thinking about me, and I felt dissatisfied with any of the options, now knowing how judgmental he was. Either he thinks I’m too pretty and so I won’t succeed, or he doesn’t think I’m pretty, which I take as an insult. 

This one comment totally changed the rest of my summer. I made conscious efforts to not look to pretty when I went into work each day, out of fear that my boss would judge me the same way he judged his girlfriend. Throughout the summer I went on to find that this was just one of many examples of what happens when you get a group of men together who aren’t used to having women around. Men in this internship would either speak their mind without holding back, or OBVIOUSLY bite their tongue whenever I entered a room.

What are your takeaways in hindsight?

Given the boss-intern power dynamic, I really don’t think there is anything I could have done differently. Especially because it was my first time meeting him. I chose not to accept my return offer at this company for full time after graduation because throughout the summer I realized that my boss would not be on my side. I didn’t have any role models at the company—I didn’t feel I had anyone that would pull me up or vouch for me. So now I’ll be graduating with a Computer Science degree from Stanford, and I’m not going to be an engineer. This is how the gender gap starts: There are a lack of females in engineering because there is nobody there to support them or just be decent to them. I’m a good engineer. I know I am. But just because of a bro-y culture and unchecked bias, I’m not going to be an engineer, because I know I deserve better than to be on a team where my boss thinks I could be too pretty to ever amount to my goals.

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