Reading "Girlboss" in 2026

Over the past week, I found myself interested in reading Sophia Amoruso’s memoir “Girlboss.” I was in search of a lighter read, and am happy to say it delivered on that promise. Despite ultimately being one of those feel-good American stories that the country manufactures to sell hope that anyone can make it, there was something about the text that I found bittersweet. Taken at face value, the story is triumphant in a way that’s very 2014. However, as the world becomes obsessed with 2016 nostalgia, it’s hard not to see the word girlboss and wonder if it was ever something… more.

For example, I see it as a term that evolved into a catchall pejorative. I commonly hear the joke “She girlbossed too close to the sun,” as an attempt to mix overambitious women with the myth of Icarus falling from the sky. In theory, it’s just a joke, but I’ve been fascinated by its etymological place in pop culture. Why do we seem so fixated on having any business-oriented woman fail just because they dream too high? I get the term can be read as pandering because of the juvenile insinuation of “girl,” but surely the idea of being a confident leader with new and innovative thoughts could be a good thing, right? Just as there have been good and bad male bosses, the same should be allowed for the opposite sex.

I’m convinced it’s because of how it fits into a box alongside Antifa or the more malleable “woke,” where those who feel insecure from the word’s intent will appropriate it to remove all context. Amoruso’s book may have been from 2014, but the ripples felt indicative of the next few years, where female empowerment led to The Me Too Movement and this push for better representation. This, of course, meant there was emphasis on the girlboss’ shortcomings, but it was also receiving a major setback thanks to the cultural black cloud, the moment we’ve been living with for almost a decade now, known as the American presidential election of 2016.

When addressing how 2016 nostalgia feels “bad,” it most often comes back to the politics, the Access Hollywood tape, the e-mail scandal, and the Pokémon Go joke run a Muk. The familiar grandstanding was now reduced to mudslinging and name-calling, contradicting centuries of candidate diplomacy. When your front-runner says to knock the crap out of protestors and that Mexico was full of criminals and rapists, it’s hard to fathom a world where any party’s PR team doesn’t try to find a respectable middle. But hey, power’s a hell of a drug.

I’m not wishing to suggest either party was, in retrospect, immaculate. However, I read “Girlboss” in 2026 and wince a little because Amoruso is the prototypical bright-eyed Millennial, still in her 20s and ready to take on the world. Her resume had dozens of jobs, and the whole shebang opens with an inspirational quote… from Wreck-It Ralph (2012). She name-drops Myspace and details at length her start on eBay that led to her Nasty Gal business taking off. Given how her story has one foot in the classical business model and the other carving a niche in the wild west internet, it’s hard not to read some of it as pure innocence, where believing in hard work would be enough to get ahead.

Maybe I’m being naive, but the mentality of “Girlboss” feels like a relic nowadays for reasons other than it came out the same year as Boyhood (2014). Yes, it captures the template for the Millennial work ethic and the optimism that opportunities were opening up, but it also falls into the traps of the generation. A girlboss, by definition, is one person. She constantly refers to her abilities as a leader, but there’s very little page count dedicated to more subservient roles. At most, you get advice on how to write her a great resume. It’s the type of mentality that may be great for those with vision and direction, but it also comes across as selfish, or at least very naive. 

Then again, I come away liking Amoruso not because I want to run a business one day, but because it pictures a brighter world than what we've got. Even the idea of searching Google Images for office furniture seems outdated just because A.I. imagery overpopulates those pages. That, and her insistence on proper grammar and politeness seem to have fallen out of fashion. I’m sure there are industries where the rare young entrepreneur thrives, but I can’t help but feel like Millennials (and those younger) have been suffocated by the economic constraints of everything that’s happened since 2016. Optimism is in short supply to the point that her empty posturing of “You too can be a girlboss!” goes from feeling like the pep talk we need to just another hashtag on social media that long ago lost its sincerity and authenticity - without which no true innovation can be achieved. 

This is all to say that I crave a world where “Girlboss” feels practical. I get its limitations as a buzzword, serving more as quirky branding, but the promise of overcoming your rough and tumble youth to have a steady job seemed like the 21st century’s answer to The American Dream. Millennials were going to adopt the internet into a grand marketplace of ideas and potential. They have, in theory, but too much is behind paywalls or relies on influencer culture to produce any persuasion. Whole industries have gone under that many spent their school years training to join. It may work for some, but the individuality that Amoruso touts is not running YouTube in the algorithm era. It’s not standing out against the bots. If anything, “Girlboss” doesn’t fathom a place where the internet evolves past the conventional supply and demand chain. Even if she seems a few steps nobler than the modern scalper, who’s to say the young ingenue who is inspired by this book stands any chance now?

So what does this have to do with 2016 specifically? Unlike 2024, when Charli XCX declared that “Kamala is Brat,” I’m not sure that Amoruso flat-out called Democratic candidate Hillary Clinton a girlboss, and yet everything about that campaign felt that way. She even promised to give her acceptance speech underneath a glass ceiling. In my mind, Clinton was THE ultimate girlboss, the one who held reason against an illogical opponent while being fawned over on Broad City. She had the track record. Following the historical presidency of Barack Obama, it made sense to keep pushing into the new. As Labyris Books put it in the 1970s, “The future is female.” 

Sure, it does seem odd for the ultimate girlboss to be generations removed and the target of valid scrutiny, but I was one of those who had hope things would pan out. Reason and compassion (as I saw it) would break through, and every embarrassing controversy would become a footnote. Never mind that her loss caused me to ruminate on how indifferent I ultimately was to her as a candidate, but when you’re in the moment, you believe in your horse even if they hobble. It didn’t help that her marketing was kind of bland and her staffer-hosted podcast was more tepid than warm milk. Credentials be damned when the other option thrived on profane levels of transparency and knew how to exploit any misquote.

Maybe it’s a byproduct of certain messaging, but the post-2016 view of The Clintons has been, in polite terms, sour. Part of it is that remnants from that election are still in the daily zeitgeist. It’s also that, because of the symbolic female empowerment that the election ran on failing, there’s some embarrassment over thinking women could be leaders. It doesn’t help that trends of misogyny and rolling back rights have increased tenfold in that time. Yes, protests have raised awareness of what needs to be changed, but without a cohesive checks and balances (or basic accountability), there’s no chance of the 2020s forming a redemption arc for the ages.

This may be why I wince a little when watching The Battle of the Sexes (2017) from the following year. It’s a great movie about tennis legend Billie Jean King dueling chauvinist Bobby Riggs. The parallels seem obvious, whether the filmmakers intended or not. Even the media circus around it felt a bit on the nose for the usually dry political campaign. Given that King won, it assumes a major win for women. I’m not wishing to suggest anyone in the crew wrote it as a girlboss movie, but it has that type of ending that is a little painful knowing we live in a world where the subtext is unrequited. 

Because of that time, I’ve become a bit too skeptical of buzzwords to evoke change. I look at social media-created memes and realize how ephemeral the exercise is. Do I want change? Of course. There are some efforts I’m more confident in than others, but I think seeing girlboss become a pejorative stings because it’s a reminder of the hope my generation had to make the world a better place. I still believe we can because I carry that stereotypical optimism. However, I think there is more of a need to be rational and dimensional, especially when the president is a Razzie-winning reality TV star (quoted in “Girlboss,” positively by the way) who insists on seeing the world in black and white when everything is illuminated in technicolor. He doesn’t want to see the full spectrum, and it’s hurting the foundation of reality. As I grapple with surface-level philosophy on what it means to have free will, things become more depressing when you realize we all had the freedom of choice (even him) to go down a more productive path. Instead, it’s a decade of mud slinging, and I hate it here.

Would I love to live in a world where girlboss was more celebrated? I’m sure that would be annoying, but it would also mean things were going in a better direction with America. It meant there was confidence to invest in programs and support a diverse economy. As it stands, I think my nostalgia is more a fond yet critical lens of what could’ve been if “Dicks out for Harambe” was as bad as things got in 2016. What is wrong with living in a country that lacks everyday conflict and innovation? I’m aware this never existed, and various non-economic issues have been brought to light in the decade since, but as someone who long believed that “more perfect union” was an aspirational term, I’m waiting for that to mean something again. Maybe it won’t take a girlboss to get us there, but hopefully the lessons of working together that developed from that conversation will move us further down the line.