Episode 43: Navigating expectations

June 30, 2014

“There’s the element of you walk into the room and you feel automatically crossed off the list. Someone is surprised at how you appear, they’re kind of taken aback. The interview’s really short, they don’t ask you a lot of questions." - Hannah Winsten

"In my 40 years as a man in the business world, I did not know failure...Suddenly I transition, and my instinct is to open businesses...which is what I attempted to do initially. And suddenly I wasn’t as successful as I was before.” - Lisa Scheps 

What happens when you're a woman at work who doesn't look traditionally feminine? We meet a couple of young women who know what it’s like to look for a job when you don’t match society's expectations of 'female'. And when you’ve had experience working as both genders, you have a unique perspective on the workplace. We meet Lisa Scheps, who had great success when she presented herself as a male entrepreneur, but as a woman in the workplace, her career has stalled. 17 minutes.

Libby Mathewson and Hannah WinstenFurther reading: When It Doesn't Pay to Wear the Pants by Hannah Winsten.

Kristen Schilt is a professor of sociology at the University of Chicago.

Lisa Scheps is co-founder of the Transgender Education Network of Texas.

The Human Rights Campaign published a report last year on transgender people's employment status.


Welcome to The Broad Experience, the show about women, the workplace, and success. I’m Ashley Milne-Tyte.

This time on the show, if a woman doesn’t present herself the way other people expect her to, the job hunt can be tough…

“We just don’t really think you’d mesh well here, it just doesn’t feel like the right chemistry,’ – these really vague kind of terms that are, like, ‘You make me uncomfortable, so we’re not going to bring you here.’”

And on the last show we heard about transgender men’s experiences at work – and how many of them have an easier time at the office after leaving their female days behind. This time, we hear from a trans woman…

I’ve talked to trans men as well and they say, 'Oh my God, no one questions what I say any more.' And I got the opposite thing. So suddenly everything I say is just questioned."

Coming up on The Broad Experience.

Last year I read a blog post by a young writer called Hannah Winsten. She made me think about something I’d never thought about before – the prejudice you can face as a woman at work if you don’t look traditionally feminine. Hannah is 23, and last year she was dating another woman she describes as butch: and butch lesbians, she says, they, often find it tough to land jobs. Her girlfriend certainly did. She was a high school math teacher. She dressed like a guy, had short hair…and Hannah says potential employers didn’t seem to know what to do with her…

“So she would go in for interviews, and you know, she had good grades, and her qualifications were the same as her classmates who were going on the same interviews as her, she’d run into them in the parking lots interviewing for these same positions. And all the feminine women who looked like me would get calls back, and she wouldn’t.”

Hannah has long wavy hair, she wears skirts, likes heels, lipstick. And she wears several work hats: she has her own communications firm, blogs on feminist matters and she’s a French translator for an online travel company. But while she was busy, her girlfriend kept coming back from interviews with nothing. And she’s seen the same thing happen to other butch women.

“There’s the element of you walk into the room and you feel automatically crossed off the list. Someone is surprised at how you appear, they’re kind of taken aback. The interview’s really short, they don’t ask you a lot of questions. You feel kind of, like, rushed in and out, like this is really not an option. So there’s that. A lot of the people I know have been told, ‘You’re just not the right fit, we just don’t really think you’d mesh well here, it just doesn’t feel like the right chemistry,’ – these really vague kind of terms that are, like, ‘You make me uncomfortable, so we’re not going to bring you here.’”

Hannah’s ex ended up finding something.

“So she did ultimately get a job, but it was in a very low-income community, which worked out really well for her. But it wasn’t a coincidence.”

That community really needed her, Hannah says. They couldn’t afford to be as fussy as other public school districts because they weren’t flooded with candidates.

It’s something Hannah’s friend Libby Mathewson has started thinking about recently. She’s also in her early 20s so she hasn’t been working long. She wears her hair short, dresses in button down shirts and jeans, and she does get mistaken for a guy quite often. She is also queer – both she and Hannah use that word more often than ‘gay’ partly because it covers more – for instance, Libby says, the fact that in general…

“I’m more gender-less, gender-neutral, I don’t really feel comfortable with either, I kind of feel like a teenage boy most of the time…but it is easier to subscribe to identifying as female as loosely as I do than trying to go completely without a gender.”

She describes herself as gender-nonconforming. And that – that can be really tricky to get people to understand – in the workplace or anywhere else.

“I’m curious, when you were in college and when you were younger, were you worried about what awaited you in the workplace?”

“Well it’s only within the past, like four years that I’ve presented masculine, so it’s kind of a new thing, and I’ve only been in the real adult workplace for about a year. Um, and it is something that concerns me, especially with my new job search, it’s something I’ve thought about, going on interviews, and I’ve definitely had the bathroom issue going on interviews…which is like, oh my God, they’re not going to hire me, this is already really awkward, I just tried to pee and now these people are, like, ‘You’re in the wrong bathroom,’ and I’m like, ‘I’m just trying to get a job!’ So it is very intimidating…”

She says because of the way she looks she doesn’t fit in either of the two doors. In the women’s bathroom she’s had mothers pull their kids away as she goes past.

She says when you’re known at your workplace for being somehow outside society’s gender norms…you’d better hope you have a good manager…

“I think it makes a huge difference, the identify of your boss – if you work for a cisgender, straight male boss, and you’re a kind of gender non-conforming lesbian, or gay person, that is a very different interaction than it you have a female boss or queer boss. I’ve worked for male bosses and there’s just the workplace sexualized culture between someone who is assumed to be female and our power figure who is a man – that is very difficult.”

She’s had some pretty awful experiences with the few male bosses she’s had so far, including one bar owner in England who expected her to sleep with clients to keep up the business. Others have expressed a prurient interest in her personal life. She’s been much happier in her most recent job, at The Urban Justice Center in New York.

“And, like, my current boss now is a woman of color, she’s straight – she doesn’t understand gender-non-conforming type of issues or transgender issues but she’s very accepting of the fact that I’m gay. And that has never been a problem and that is very respected throughout my workplace.”

Hannah says things are different for her – people just assume she’s heterosexual because of the way she looks. And that isn’t always ideal either.

“If I go out to hang out with coworkers after work, for happy hour or whatever, I was in the middle of a breakup, we’re talking about my ex, and I have to specify, you know, who my ex is and what, you know, my future dating prospects are.  And it can be a little awkward, it can be a little uncomfortable.”

As people have to suddenly digest the fact that she’s not what they thought she was. She says it would be nice if no one assumed anything from her appearance. But both she and Libby are quick to point out they’re quite privileged – both went to NYU, a top US college, and they’re both white. They know a lot of people in the LGBT world whose parents have thrown them out, who either can’t get a job at all or they’re underemployed. They feel pretty lucky.

Last time we heard sociologist Kristen Schilt talking about her research into transgender men’s lives at work – and how two-thirds of trans men she studied found life as men in the workplace easier than their old roles as women in the workplace. She told me there’s a real difference between how co-workers react when a man or woman says they want to transition. She says when it comes to trans guys – their bosses and co-workers seem to get it:

“They didn’t have a lot of questions about why a woman would want to be a man. There was sort of an assumption of like, well, it is pretty good to be a man. But you know, it’s been really striking to me interviewing transgender women, with how much opposition people have to it, particularly men, about, ‘But why would you do that to yourself? You have all these great things with being a man. Why would you want to become a woman?’”

She says those male co-workers didn’t seem to worry about what taking testosterone might do to their trans colleagues. In fact they viewed testosterone as a good thing – something they might like more of themselves.

“But transgender women get asked a lot of questions about estrogen, which has been interesting. And a fear almost of estrogen, so, ‘If you take estrogen are you going to be unstable? Are you going to be moody? Is it going to change your ability to program a computer? Are you going to be thinking about makeup and clothes all the time? And so there was a lot of concern about estrogen as something that was going be a detriment to transgender women’s experiences, or abilities.”

Lisa Scheps knows all about those concerns first hand. She’s a trans woman who transitioned about 13 years ago. She’s co-founder of the Transgender Education Network of Texas. She lived her first 40 years publicly as a guy – she says she realized early on anything else was unacceptable.

“Oh, there was a lot of pretending that went on. I guess for the first 4 or 5 years of my life everyone knew I wanted to be a girl and everyone was OK with it. But at some point growing up male in Texas in the ‘60s you learn cues from society and your parents. Suddenly it wasn’t cute any more. And I learned very quickly that in order to survive in the world I would have to play the game. So I became a very rough and tumble little boy. I did boy very well.”

She did man pretty well too, for much of her adult life. But at home, Lisa was living as a female. As she approached her 40th birthday, she was living in Chicago, running a business with three male partners. And she decided she just couldn’t live this double life any more. She wanted to come out – to transition, take hormones, change her appearance, live openly as a female.  

Her colleagues knew about her transgender life - but they felt as long as she kept presenting male at work, that was fine with them. At first, they seemed OK with the idea of her transitioning, and staying on in the business. But actually, they were far from OK…

“Unbeknownst to me they had been meeting and planning this for quite some time. They did not want to find a solution. They wanted me gone. So we spent the next day negotiating, negotiating, and it started getting very personal. They started giving me personal attacks. For instance, one person said to me, ‘How do you expect to deal with business when all you’re going to be thinking about is nail polish?’”

That estrogen again – turning women’s brains to mush.

Her partners pushed her out of the business. Her whole life had been tied up with Chicago and work. But after her work world caved in, she moved back to her home state of Texas. 

“I moved back to Texas because my family was all here. And one of the interesting things that happened in my coming out process, I had a very typical southern Jewish family where everything was done on the surface. There was no intimacy in my family at all. When I came out it forced a certain amount of intimacy in my family that we had never seen before. So on a strange level we got a little closer.”

Meanwhile, she began looking for work.

AMT: Talk a little bit about what it’s like to be a working person now as opposed to how it used to be.

“Well I’ve always been an entrepreneur. So I’ve never really been an employee of anybody other than myself. I’ve always done my own thing. So I don’t have a frame of reference as an employee in the standard working environment. I can tell you this, though: In my 40 years as a man in the business world, I did not know failure. Success came very easily to me. Even though in what I was thinking, that I was doing it all on my own, pulling myself by my own bootstraps. I didn’t realize being a white male in our society was a pretty big boost up to success. So I did not know failure. Suddenly I transition, and my instinct is to open businesses, or fend for myself, which is what I attempted to do initially. And suddenly I wasn’t as successful as I was before.”

She survived on savings for quite a while after her transition – after all she had been earning a high six-figure salary as a partner in her Chicago business. But her exit from the company had been painful. She didn’t negotiate as well as she should because of all the angst surrounding her departure. She needed money and she just couldn’t make it the way she used to. Just before the economy crashed in 2008 she got together with one of her former business partners and opened another company. And during that time, interacting with clients as a woman in the workplace, she says she didn’t feel any difference in treatment at the executive level, it was the people in middle management who made her feel different. I asked if she felt a loss of status.

“Absolutely, I felt a great deal of loss of status. You know in our culture everything a man says – and specifically it’s really white, upper-middle-class men – but let’s just says everything a man says is taken at face value. Everything a woman says is questioned. So if you are grown up and are socialized in one gender or the other you’re accustomed to that, you don’t even think about it. But when you go from one to the other – and I’ve talked to trans men as well and they say oh my God, no one questions what I say any more. And I got the opposite thing. So suddenly everything I say is just questioned. No matter what it is or when it is. My expertise is questioned.”

Which came as a huge shock to her after years of running a business where clients trusted her expertise. That company she started with her business partner? If failed after the recession hit.

I wanted to ask her about something Chris Edwards, a transgender guy, talked about in the last show. If you heard that show you’ll remember he mentioned what happened to his personality after he transitioned and began taking testosterone. He began to notice changes like becoming more curt and to the point, speaking up more in meetings, interrupting more and listening less. Lisa says she also noticed changes in her personality – she says she’s definitely a better listener these days - but she doesn’t believe these changes that she and Chris went through have anything to do with taking male or female hormones.

“I think we like to think that. As a trans person, you know, I do know that when I started taking estrogen I was hoping that suddenly, like, I would turn into the stereotypical woman that I had in my mind that I was going to be.”

So who was that?

“Oh my Gosh, you shoulda seen…right after transition I turned into this itsy little flower of a person that shrank into myself and got very, very quiet. That’s not who I am. It took me a long time to understand that pieces of my personality that I liked, and things that I did that I liked, like aviation, I’m a pilot, I’m a scuba-diver, I’m a risk taker. These are things I like about myself and just because I am now female doesn’t mean I have to let go of that.”

She’d had a distinct idea of what a woman was. She says the changes to her personality that have occurred have happened because of socialization. She’s around women a lot more now. And she’s become more and more aware of how society expects women to behave. She’s adapted accordingly – to a certain extent. But the flipside of finally living openly as a female?

“I have gotten a job here at my community radio station and with some nonprofits here. For the past year and a half I’ve been an employee for the fist time in my life. But the jobs I have were secretarial in nature and administrative in nature. I do not and have not been given responsibility.”

Something she would love to have again. Now you might say, but what if all this is down to prejudice against transgender people, not women? Lisa’s thought about that. Transgender people are much more likely to be unemployed or underemployed than the population as a whole. And she knows lately, as there’s more information about her on the internet that makes clear she’s a trans activist…maybe there is some bias against her on that score as employers Google potential candidates. But as Kristen Schilt mentioned earlier and in the last show, her research show trans men are less discriminated against at work than their female counterparts.

Lisa wouldn’t change anything about transitioning – except her employment situation.

That’s The Broad Experience for this time.

Next time on the show…what can happen when a woman comes back to work after having a baby – and what we can do about it.

“All of a sudden, all of these things that the workplace seemed to accept about these women and they accepted about themselves, and the trust they had earned in these companies, had been sort of thrown out the window, and they’d been put under this intense scrutiny as if they weren’t as committed to their jobs.”

That’s coming up in two weeks.

You can comment on this show at TheBroadExperience.com or on the show’s Facebook page.

If you like what you hear, please spread the word on social media or by old-fashioned word of mouth.

I’m Ashley Milne-Tyte. Thanks for listening.