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At 32, I've never had a paid job with a female boss. From my first job lifeguarding at a suburban swimming pool to my current one at a software platform startup, I've been hired and managed by dudes. Some of them have been brilliant mentors and others have been sociopathic tormentors; some, like the manager of the swimming pool, were incompetent but benevolent lummoxes. But they all had one thing in common: their Y chromosomes.
Until recently, it hadn't occurred to me to be worried about this. Well, I was worried about what the lack said about society, but it didn't seem like it was having any adverse affect on me, personally. Then, two years ago, I started a company. Since then, it's become clear to me that in order to achieve the goals I have for myself and my business, I'll have to become a boss myself, and without a female role model, it's tough to figure out exactly how to finesse many of the situations I now find myself in.
How do you win your team's approval without just defaulting to being a class clown, co-conspirator, or indulgent pal? What am I doing that's actually hurting my progress, and how can I stop? How do I balance being decisive and clear with wanting to be liked and needing to be respected? And maybe most importantly, how do I reconcile my belief that our current economic system is both evil and doomed with my need to make and spend increasing amounts of cold, hard cash? I picked up #GIRLBOSS by NastyGal founder and CEO Sophia Amoruso hoping to get some answers.
Amoruso at a signing. Photo via Getty.
#GIRLBOSS is positioned as a Lean In for millennials, and like that book, it uses the author's life story as a series of instructive lessons for those who would follow in her footsteps. But unlike Sheryl Sandberg's straightforwardly ambitious route, Amoruso's path was circuitous and decidedly unconventional. Though her online clothing boutique is now a 300-person company, it started as an eBay vintage store that she ran out of her apartment, and a refrain throughout #GIRLBOSS is that Amoruso never "meant" for this to happen: "I never would have done it if I'd known it was going to become this big."
She got her first online retail experience shoplifting bestsellers from chain bookstores and reselling them on Amazon while living a "crust punk" lifestyle of hitchhiking, dumpster-diving and meeting with a Marxist reading group. I expected slightly more analysis of her transition from freegan to CEO, but #GIRLBOSS keeps it brief: "I believed that capitalism was the source of all greed, inequality and destruction in the world. I thought that big corporations were running the world (now I know they do) and by supporting them, I was condoning their evil ways (which is true, but a girl's gotta put gas in her car.)" She got sick of "agonizing over the political implications" of her lifestyle and realized that she liked "nice things." Like most people who capitalism is currently working out extremely well for, she's way over thinking about the structural implications of the system that makes it possible for her business to thrive.
Inside Nasty Gal's HQ. Photo via Lazy Oaf.
Okay, so there are no answers to big philosophical questions in #GIRLBOSS; I resigned myself to finding some solid tips on how to be a manager and a woman simultaneously. Amoruso, at 30, finds herself running a company worth millions of dollars, and she's up front about having a no-nonsense management style. But that's about as much detail as the #GIRLBOSS reader gets. There are only 20 pages in #GIRLBOSS devoted to actual advice, and none of it is directed specifically at girls. Most of it isn't even directed at bosses. Instead, we get a chapter called "On Hiring, Staying Employed, and Firing," which is more focused on what it takes to get an entry-level job; Amoruso describes what she's looking for when she hires at NastyGal and what turns her off in a cover letter. Entitlement and laziness are big no-nos, as are the words "that's not my job." A chapter subheading, "You Are Not a Special Snowflake," has as its epigraph a Joel Stein quote about how millennials got too many participant trophies when they were kids. Amoruso tries to soften the blow by lumping herself in with the readers she's admonishing—"A lot of people in my generation don't seem to get that you have to work your way up"—but coming from a phenom whose most impressive pre-CEO job title was Subway "Sandwich Artist," this rings a bit false.
Like most people who capitalism is currently working out extremely well for, she's way over thinking about the structural implications of the system that makes it possible for her business to thrive.
There are a few tips for bosses in that chapter, though, and they're all solid, if commonsensical: don't complain about how tough firing someone is for you while you're firing them (it's tougher for them), don't befriend your direct reports (they'll hurt your feelings when you open up to them about how your new Porsche makes you feel cheesy), and if you think you might fire someone, start documenting everything. But nowhere is there a mention of the unique challenges women face on their journey towards becoming #BOSSes, like balancing work and family, negotiating salaries, and generally walking the line between being persuasive and powerful and being perceived as "pushy" harridans.
But maybe this is progress? In her introduction, Amoruso writes, "Is 2014 a new era of feminism where we don't have to talk about it? I don't know, but I want to pretend that it is." And while that's kind of maddening, I can see why Amoruso decided not to beat any dead horses and to write a book that's full of implicit feminism, rather than dogma: dogma is boring, and #GIRLBOSS (and, by extension, Amoruso) is about looking great, working hard, and having fun, ideally in a Porsche. When she was building her business, she clearly didn't stop to consider how she'd be perceived (I mean, "NastyGal"?), and that lack of self-doubt might be the book's most inspiring lesson, even though it's not a lesson that can easily be put into practice. But then again, neither are the takeaways from Lean In," and #GIRLBOSS has much better jokes: "Joanne was really tan, like a homeless woman or someone from Malibu" was one of my favorite lines. If we're still waiting for the female boss memoir to rule them all, at least we can laugh while we're waiting.