Transgender on Wall Street

Wall Street has long had a problem with all things female.

Its ingrained bro culture, detailed in author Susan Antilla's 2002 blockbuster book, “Tales from the Boom-Boom Room," might no longer include toilet bowls hanging from ceilings and Bloody Marys served during morning work hours. But post #MeToo, instances of harassment and discrimination persist.

In a tell-all memoir last summer, for example, Jamie Fiore Higgins, a former managing director at Goldman Sachs, described the bank’s culture of sex, drugs, strip clubs and misogynistic comments (she got her job “because of [her] vagina” was one). In May the bank agreed to pay $215 million to settle a class action alleging sexual harassment and wage bias against women.

So what happens when a woman reaches the highest levels of finance but was assigned male at birth?

Could the experience of Maeve DuVally, a managing director of communications at the white-shoe bank from 2004 until June 2022, mark a shift? By her own admission to The Messenger, not by everyone.

For most her career, Maeve was Michael, an executive at the highest rungs of finance, eventually twice-divorced and with three children. Then on May 29, 2019, everything changed. Michael, born male, walked into the 29th-floor office officially as Maeve.

For the first time, she was wearing heels, lipstick, a blond wig and a conservative, black pantsuit over a fitted knit shirt that "shamelessly flaunted the small boobs," DuVally wrote in her memoir, “Maeve Rising: Coming Out Trans in Corporate America,” which hit bookshelves last month.

She recalled being greeted with hugs and compliments about her outfit and lash extensions. Ed Emerson, the head of Goldman's powerful commodities trading desk, sent over a bouquet of flowers from his team.

Since leaving Wall Street, DuVally, age 62, has been doing public speaking, serving on the boards of LGBTQ+ nonprofits and mentoring trans and queer people in recovery. She’s also writing a novel set on Cape Cod that explores different elements of identity in the lead character, a trans person.

DuVally sat down with The Messenger to talk about her experience at Goldman, blush and the biggest misconception about trans people.

The Messenger: Do you recall the first time you started wearing makeup?

DuVally: Eight or nine months before [officially going to work as Maeve], I got sober. I'd been trying for a long time but kept relapsing. This time around, it's stuck. I kind of took a deep look at myself, and I think that opened me up to finally having the experience of realizing who I was.

It was at the Sephora in the Oculus [an indoor shopping mall at the World Trade Center in Manhattan]. I bought what I thought was foundation but it was powdery blush — blush all over my face! I probably had like a Donald Trump orange tinge. I didn't know what I was doing. So I bought that, and a lipstick and a little hand mirror. I bought mascara as well. I don’t remember the brands. But I spent a long time in there because I was very nervous. 

The Messenger: What about women’s clothes?

DuVally: I wanted to start someplace that wasn't that expensive, so it was a Loft on the Upper East Side. I bought tight jeans. I bought, like, this frilly yellow blouse. I bought a pink sweater. I bought pink corduroy pants. I bought a lime green sweater.

I kind of had this fear that the gender police would come and lock me out — that somebody who looked like a male was buying female items, and somehow I was gonna get busted. And I didn't want to ask anybody for help. So I walked around the store reaching for items and then finally I gathered what I considered a critical mass and got the hell out of there.

The Messenger: Tell me about the first time you felt you were authentically yourself at Goldman.

DuVally: I told Goldman in January 2019 that I was transgender and wanted to transition at some point but wasn't ready to do. Then in April of 2019, I decided I did want to transition. So I worked with the people in human capital management — that’s what we call HR — and we came up with a plan.

Part of the plan was identifying people we had to tell in advance, both internally and externally. Most of the people around me in my immediate group, which was corporate communications, and adjacent groups — investor relations, corporate philanthropy — were [already] aware. So it was no surprise when I walked in on May 29, 2019, the day after Memorial Day, fully dressed as Maeve, not as my previous self anymore. 

I had gone that weekend to Bloomingdale's and bought a whole bunch of new outfits I could wear that first week. I had a friend who worked at Bloomingdale's who helped me choose clothes. She basically looked at me beforehand and tried to estimate my size. And she had gotten a whole rack for me and sent it to a part of the floor where there were dressing rooms that most people didn't use.

You know some some dresses are pretty hard to get on, right? And so I put them on and I said, ‘I can't get it off!’ Or I was worried that in getting it off, I was gonna rip this $500 dress. I ended up early on buying a lot of clothing from Theory. It seems to fit me well. And it's very professional.

The Messenger: How did you feel walking into work that day?

DuVally: Every time I do something for the first time, it kind of makes me nervous, but once I go through it, I’m okay. Why did I get nervous when I was doing something related to my appearance for the first time? Because I thought I was going to look freaky.

The Messenger: What you mean by "freaky"?

DuVally: Stupid. I’m not sure I can define it, but I was worried that I wouldn't be comfortable and people wouldn’t think it looks very good on me. I didn't didn't want to look like I was a man. It caused me a lot of anxiety. Dresses were a higher risk than pants for making me look weird.

The Messenger: Did you encounter any micro-aggressive comments at work?

DuVally: No, no, none that I know of. I was just talking to another trans person about something related to this today, and I think that person had seen one of the stories written about me, where I was talking about the good experience I had at Goldman Sachs. And this person worked for another bank, and said she did not have a good experience with that bank. And I said, 'I'm sorry.' But I also had to admit that these experiences are very subjective. 

What I have now is nirvana. I'm sober. I know who I am. I had a great career at Goldman Sachs. I'm doing my own thing. I wrote a book. I'm sitting here talking to you. You conceivably want to hear what I have to say. This is just so good, I can’t even describe it. 

On one level, it certainly would have been nicer for me to realize I was an alcoholic and get sober earlier in my life. And if that had happened, perhaps I would have realized I was transgender earlier.

The Messenger: Tell me about your relationship with your children.

DuVally: I have a daughter by my first marriage. She's 35. And then my older son, Liam — he just graduated from the University of Vermont. And my younger son, Connor, is a rising freshman who's just about to go there.

My daughter pretty much accepted me from the start. In early 2019, my son Liam was four or five months later going to graduate from high school. And he told me, “Just chill — I'm going to be good once I once I graduate.” And he was true to his word. And I will say that his graduation was the last time I ever wore men's clothing. And I actually took my suit off while I was driving my car, and I never looked back. 

My younger son Connor clearly accepts me. He's a teenager right now, so we've never really kind of talked about the whole thing. I think when he gets a little bit older, we will have that conversation

I'm very fortunate with my extended family — I was raised in rural Massachusetts. Most of my family is more conservative than I am. Maybe my brothers in particular don't really understand this. But they have accepted me, and they've seen that I'm a much happier person. And that's good enough for me.

The Messenger: What's the biggest misconception about trans people?

DuVally: The biggest misconception is that a transition is an external process. Many of us take hormones, many of us get surgery. And we need to do that to get our physical appearance to a place that makes us feel more comfortable with ourselves. But the most important part of the transition is the internal part.

I identify as a woman, and I will tell you that the most meaningful and satisfying part of my life thus far is when I am accepted by a group of women. I recently went to a spiritual retreat with some people in my recovery network, and I was completely accepted by the women there. There was just no question that I belonged there. And that just feels very empowering.

This interview was edited for length and clarity.