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A number of 2021 films and televisions series were criticised for exemplifying the term, such as Physical.

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To some, Holmes served as 'the quintessential girlboss,' and her trial revealed many of the shortcomings present within the girlboss ideology and, more broadly, the attempts to use feminism in order to minimize women's accountability regarding their decisions. In 2021, some social media influencers attempted to redefine the term as 'a sort of post-ironic area in which female evil is celebrated', such as over the trial of Elizabeth Holmes. Judy Berman of Time stated that the rise of anti-capitalist sentiment among youth had turned the term 'into a joke, a meme, something hopelessly cheugy.' Alex Abad-Santos of Vox argued that the term has 'shifted culturally from a noun to a verb, one that described the sinister process of capitalist success and hollow female empowerment,' pointing to the parody phrase ' Gaslight, Gatekeep, Girlboss.' According to Amanda Mull of The Atlantic, this time saw the 'end of the girlboss' manifest in a 'cultural pushback'. Later in 2020, the George Floyd protests saw a number of high-profile women executives resign after accusations of creating toxic and racist workplaces. In early 2020, the self-regulatory organisation Advertising Standards Authority (ASA) banned a billboard, advertising PeoplePerHour, which read: 'You do the girl boss thing we'll do the SEO thing'. Martha Gill of The Guardian writes that feminist movements can 'push for change and help women in an imperfect world,' yet still 'celebrate women who succeed anyway.' However, some believe that individual women's achievements can still be praised, and that this is not mutually exclusive with also working towards better workplaces and positive change on the societal level.

Some audiences began to critique the girlboss for pursuing individual successes instead of working to weaken the forces of the patriarchy and pursue broader structural change. In 2022, Amoruso herself tweeted 'Please stop using the word Girlboss thank you.' By 2019, the concept had begun to derive disdain from some women and viewed as ironic others still believed in its worth. Its popularity led to it becoming a 'a template for marketing and writing about powerful women in virtually every industry'. Its early usage was defined by perceived empowerment. The term became popular in 2014 after Sophia Amoruso used it with a hashtag prefix in her bestselling autobiography, which was adapted into a TV show of the same name.

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The term is conversely used with sarcastic and pejorative undertones, to denote women who attempt to raise their professional lives by practicing the same abusive and materialistic practices found in the patriarchal society. Popularised by Sophia Amoruso in her 2014 book Girlboss, the concept's ethos has been described as 'convenient incrementalism'.

Girlboss is a neologism which denotes a woman 'whose success is defined in opposition to the masculine business world in which she swims upstream'. For the television series, see Girlboss (TV series).

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