Lark (20s me): Hey, can I talk to you?

Mom (Present me): Of course, Lark. What’s on your mind?

Lark: Something has been bothering me about us. I spent a lot of time trying to find ways to make money — Find a profitable venture, invent the next big thing, write a smash hit video game, anything. I’ve been visiting our recent memories and it feels like that dream is dead.

Mom: It isn’t the priority it once was.

Lark: Becoming independently wealthy was one of the great goals of my life. And now it barely matters? What happened?

Mom: You said that dream was one of your life goals. One of two.

Lark: Right… The other was getting married and starting a family.

Mom: Yes. And we achieved that goal. I’ve been married for years and am a proud parent. I think that deserves some recognition.

Lark: Okay sure, that’s a big deal, but there’s still this other goal. And it’s still unfulfilled.

Mom: We’re financially stable. Tech still pays well, after all.

Lark: It could pay better. With your experience you should be a director by now!

Mom: If memory serves you weren’t exactly concerned with traditional career advancement.

Lark (sheepish): I mean… I was never going to get rich working for someone else… And the culture at my company is so rigid…

Mom: That sentiment sticks with you throughout your career, even after you’re working at better companies.

Lark (tearful): I know it’s my fault our career doesn’t take off. I stayed in my first job too long, I never learned to negotiate properly, and I hate hunting for jobs.

Mom: It’s not your fault, Lark. I believed that it was for a long time, but I don’t think it’s true anymore. We were given the education to be productive workers, but not the tools to think critically about what being a worker meant or to recognize when we were being exploited. Our elders and teachers encouraged us to get ahead, to beat the odds. Just like everyone else. And most people can’t; that’s what odds are.

Lark: So our elders’ are to blame?

Mom: I don’t think assigning blame is particularly useful. I think there’s a willful systemic blindness in the people and culture that raised us, a culture enamored with the idea of individual freedom and the illusion of a just society. We were taught that the only thing that can change is ourselves, so it was our responsibility to conform to the systems we found ourselves in. We were exploited by those above us, and didn’t understand that things shouldn’t have been that way.

Lark (crying): I mean, I still knew things weren’t great! I knew I would never get ahead just by working, it’s why I put so little effort into advancing my career. But I figured I was smart and clever, and I was taught that was enough. If you were smart, you could beat the odds.

Mom: And you saw your smart peers, people who took the same advanced classes as you growing up, getting ahead where you couldn’t. You watched them prosper as you struggled and you wondered why you weren’t smart enough; what you were missing.

Lark: That sucked so much… Feeling like I was falling further and further behind my peers. It still stings.

Mom: I know. But you couldn’t have walked their path.

Lark: But why!? What did they have that I don’t?

Mom: You have it backwards, Lark. You have something they don’t. You’re a trans woman.

Lark (upset): What!? I know women have a harder time in the workplace, but nobody saw me as a woman! So how could that matter?

Mom: It’s not so much the “woman” part as the “trans” part. Being trans meant that the gender role you were expected to fill fit you very poorly. Even if you didn’t realize it, there was always this constant friction between you and the rest of life, and that friction is emotionally draining. Between your work and the values you were taught and your dreams of making it big, there wasn’t anywhere you could go to escape it. You were always fighting it. Your peers weren’t.

Lark: But surely they had their own challenges?

Mom: Everyone has their own challenges. Constantly spending most of your emotional energy just fitting into your social role is a heavier lift than many though.

Lark: So I didn’t have enough emotional energy to work hard and get ahead.

Mom: Not that. That just meant your employers couldn’t exploit you as efficiently as they would have liked. Actually getting ahead in business isn’t about hard work, it’s about pleasing the right people. Networking, navigating office politics, knowing what to prioritize and when; all of those are emotional tasks too. And when you’re already barely keeping your head above water emotionally there’s no way you can meaningfully engage with any of those tasks — especially when you not only have to do them well, but do them better than the people around you. It’s a competitive game and the entire deck is stacked against you.

Lark: So by honing my intellect and focusing on my skills, I wasn’t even playing the right game, so to speak.

Mom: And thanks to the beliefs drilled into you around being a good employee, you didn’t realize there was another game to play. So you were exploited, like so many other women starting their careers. As you pointed out, you weren’t perceived as a woman back then, so the shape of your exploitation was different. But it was exploitation all the same.

Lark: Okay, hang on a moment. If I had figured this out and transitioned, I would have been perceived as a woman, and I would have been exploited like a woman.

Mom: And as a trans woman on top of that.

Lark: So it feels a little disingenuous to say that transitioning would have solved our problems.

Mom: Which is why I didn’t say that. You’re a woman; your path was going to be difficult no matter what. All I’m saying is that you didn’t realize you were a woman, so you were comparing yourself to privileged white cis men and wondering why you kept coming up short.

Lark: I… Hm. I don’t know what to think about that.

Mom: That’s okay, Lark. All I ask is that you sit with it for a while. Feel it out and see where that takes you.