Lonely at the Top: Being a Lady Boss Without Mentors

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Photo: Getty, Fox and AMC

Two years ago, when I was 29, I accepted a job with the word “executive” in the title. I’d read all the studies on women in management positions and was understandably nervous about being a boss. Female bosses are often considered less likable by many accounts, and not just by male employees. In one British survey, a quarter of women said that female bosses were more likely to be insecure backstabbers, who brought their personal baggage to work and spent too much time worrying about their appearance. I didn’t want to be like that, but didn’t know what a good boss looked like either.

Of the handful of older women I’d worked with, some seemed to be resentful of me, prone to lectures about how hard they had it in the deeply sexist early days of their career. Others weren’t exactly hostile, but still kind of cold. A few clearly wanted to mentor me, but had to be home at 5 p.m. every day for their second shift. And there was also a whole swath of women aged 30 to 40 missing entirely from the workplace, due to the Mommy Gap, which may help explain the existence of twentysomething bosses in the first place. 

Even though I’d been working with professional women for about a decade, I failed to come up with even one mentor-type figure I felt like calling up for advice. After reading this week's interview with Irene Dorner, CEO of HSBC USA, in the New York Times, I found myself again struggling to name a single female mentor. Though she comes from the business sector and not media, her words rang true: “I suspect that we were simply not very good role models,” Dorner said. “And there aren’t enough of us to be visible so that people can work out how to do what we did.”

Tell me about it. I was relatively young when I became a boss — right around the same age as everyone I would be managing — so I worried about how to establish myself as an authority without seeming like an asshole, how to be that boss I always wanted for myself. From day one, I took pains to separate my personal life from my professional life. (Turns out this isn’t that hard when you’re working all the time and have very little personal life to speak of). I wanted to be stylish but asexually professional, so I adopted a uniform that I thought fit the bill (silk blouses, jeans, ankle boots). I made it a point to work longer and harder than everyone I managed, but aimed not to complain about it. I also tried not to do anything a former boss had ever done that annoyed me. I remembered one time when a boss had introduced me as someone who “worked for him,” and how I’d thought to myself, “I work for the company, not for you.” So I watched my language and made it a point to always say, “She works with me.” Or “We work together.” It was more accurate, anyway. 

Even though women have been making incremental progress in the professional world, I’ve suffered the same acute lack of older female mentors as women of previous generations. While I’ve learned many important lessons from male bosses I’ve had, it’s no secret that powerful women face some particularly thorny issues as they try to be effective leaders. Be nice but not too nice. Firm but not too firm. Personal but not too personal. More than once in my career, I’ve thought that it might be nice to have a woman in the next office over who’s been there before and might have a few words of wisdom to impart about the gender landscape of the professional world, about how it looks five or ten years from now (or even five or ten years ago).

When it came time to mapping out the best way to project authority and get the job done without becoming reviled in the workplace, I muddled through on my own. Needless to say, this was exhausting. My “fake it til you make it” approach to boss life helped me project confidence and earn respect, but my unshakeable outward composure took a toll inside. A Gchat transcript from my second week on the job catches me already revealing to a friend, “i haven't cried since taking this job and i feel like I really need to but i can't.” (Maybe it was the sheer exhaustion, or maybe this is getting at some deeper personal issues.) Or, a few months later, “oh i just had a tough day and was feeling some boss-lady isolation.” 

My lack of mentors was thrown into relief one night when I was out drinking with some friends and the conversation turned to Anna Wintour. She seems like such a bitch, someone said — the sort of casual assertion you make about celebrities you’ve never met. I knew that this had nothing to do with me. But it still managed to cut through all my self-protective mechanisms. I realized on a gut level that I identified with this abstract caricature of a boss lady — and the criticism of her was exactly what I feared I’d be labeled when I was assertive at work. I just stood up abruptly and walked home. Later that night I read an essay from Rachel Cusk in Granta, and copied the following passage in my journal, longhand: 

“‘Having it all,’ like any form of success, requires hard work. It requires an adoption of a heroic mode of being. But the hero is solitary, individualistic, set apart from the human community. She is a wanderer, forever searching out the Holy Grail, forever questing, pursuing the goal that will provide the accurate reflection of her own abilities. The hero, being exceptional, is essentially alone.”

So emo, right? But that’s how I felt. The media narrative about boss ladies is that they are lonely and a little bit miserable at the top. Not just the popular perception of real-life figures like Anna Wintour, but fictional characters from Sigourney Weaver in Working Girl to Elisabeth Moss on Mad Men to Jennifer Lopez in The Wedding Planner to Tilda Swinton in Michael Clayton to Christine Baranski on The Good Wife. Or, as Mindy Kaling writes about rom-com stereotypes in her memoirs: “The woman who is obsessed with her career and is no fun at all.” It would have been nice to have an older woman to tell me she had been there and it wasn’t that bad — even if that was kind of a white lie.

Without a go-to older mentor figure, I turned to professional women my own age. I bombarded my friends with questions about how they’d like for a manager to tell them they had to work this weekend or that they weren’t getting a raise. They always obliged, but it wasn’t quite the same thing as consulting a woman who’d been in the boss position herself.

I worked such long hours that the people I managed became some of my best friends — which was less lonely, but tricky in its own right. It’s tough to talk about deadlines or budgets or push back against an inconveniently scheduled vacation when you’re managing your friends. I still made an effort to keep my personal life cordoned off — not spending too much out-of-work time with my co-workers, for example. But when that rule fell apart, it really fell apart. After one particularly tough conversation with the whole staff, we all blew off some steam together. An e-mail I wrote to a non-co-worker friend later that night reads: “then we got so drunk and dacned to soul music and i just now dropped 2 bbq potato chips inot my ankle boot.” So much for professionalism.

When I asked one of my former co-workers, Zak Stone, about his initial impression of me, he forwarded me our first IM conversation, in which I noted that his chat avatar was Rihanna riding a zebra and proceeded to ask if he’d seen what the pop star had just worn to the Met gala. “Yeah, I guess that was when I realized you were cool,” he told me later. And what about prior to our Rihanna bonding moment? “Before I thought you were just really serious. In a good way when it came to taking care of biz,” he replied, “but possibly in a bad way when it came to just being a chill person? I dunno, I think I was intimidated slightly.” Looking back, I suppose that was kind of my strategy. It’s hard for women to convey both accessibility and authority.

And then there was that time I was giving Amanda Hess, an editor I worked with, a ride home and she said, “You’re a really good boss, Ann. You’re doing a great job.” I almost started crying. “Really?” I asked her. I couldn’t believe it. A year or so later, after I’d long forgotten about this moment, she reminded me of the conversation. She told me she thought it was silly that I was so surprised to hear I was doing a good job when, at the time, she felt silly for pointing it out. Or, as she explained simply: “I thought it was obvious.”