Thoughts on Being A (Cool, Lady) Boss

Workplace inequality set to a jaunty tune!

Above is the inimitable Rachel Bloom of Crazy Ex-Girlfriend, the best show on television that is also a musical about mental health, singing about the vagaries of being a lady boss, complete with internalized misogyny, a Ruth Bader Ginsberg pillow with which to muffle your sobs from behind a closed door, the success of one woman meaning the inevitable failure of another, and an eternal struggle for all women in the workplace, regardless of their position — how much boob is too much boob?

For a slightly different take on the “lady boss” thing, you could turn your attention to Netflix’s recently released Girlboss, based on the memoir of Sophia Amuroso, the CEO of Nasty Gal, a company that filed for bankruptcy in 2016 and was plagued with a host of management issues stemming from the Girl Boss herself, including firing four newly-pregnant employees and terminating one man who was set to go on paternity leave. Very cool.

I read the memoir when it came out because I was sort of interested in seeing how someone could make a business from virtually nothing. My review of the book is brief: I don’t remember much about it because I have a bad memory, but also because it probably wasn’t that good. If I was really invested in figuring out the secret to Amuroso’s success, I guess I’d turn to the Netflix show — and I still might, we’ll see — but the reviews are, uh, not awesome.

Netflix’s Girlboss Is a Letdown

“I just need to figure out a way to grow up without becoming a boring adult,” says Sophia in the first episode to a woman sitting next to her on a San Francisco park bench…

The fact that she has a point is confirmed a few minutes later, when Sophia shows up really late to her job at a shoe store, talks back to her supervisor, takes personal calls instead of helping customers, then eats her supervisor’s sandwich for lunch without asking. She gets fired, then flips out and says she’s actually quitting, storming out of the store as though she has every right to feel outraged for being held accountable for her behavior. While talking on the phone with her best friend, Annie (Ellie Reed), about what just transpired, she has a sudden moment of regret. “Why am I such an asshole?” she asks, her eyes filling with tears.

Yikes!

But if you’re interested in what it’s like trying to juggle being a Cool Boss with actually, um, doing your job, here’s a good meditation from Doree Shafrir.

How I Tried and Failed to Be a Cool Boss

Transitioning from being a cool coworker to a cool boss is tricky stuff. Aside from the added responsibility of being a boss — meetings, so many meetings, more meetings, phone calls — there’s also the feeling of what to do with the work stuff you used to talk about with your coworkers when they were just your cowokers and not your direct reports.

After a few years, I’d had enough. I think it takes a particular kind of person to be a good boss — someone who cares less about what people think of them, for starters — and I was feeling like I was not it. Certainly, the social aspects of my job were not the only reasons I was unhappy — I was coming home stressed every night, answering emails and chats at all hours — but I felt socially isolated in a way that I never had when I was just an employee.

When you’re not the boss, you have outlets if you’re feeling frustrated at work, or have a problem with co-worker. When you’re the boss, you don’t: It feels unseemly, for one thing, and for another, there just aren’t as many people around to complain to. You can’t complain to the people who work for you, for obvious reasons, and I also felt like I needed to maintain this brave face with my boss. So my husband and friends outside of work bore the brunt of it — but of course, they couldn’t really understand what I was struggling with.

Shafrir stepped down from her position and took a job as staff writer which left her much, much happier. Amuroso’s business crashed and burned. Rachel Bloom is presumably still the boss of the many people who work on her show. Being a “cool” boss and being a good boss aren’t problems exclusive to women, of course. Maybe there aren’t any commonalities in these three stories — just three women who happened to be in charge in very different circumstances.

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