[2] Her brother, Geoffrey Whitney (named after their father), was a notable author of the time whose works include A Choice of Emblemes and other Devises (1586).
The Wilkersley court records for 1576 show her father being fined for the fact that his unmarried daughters, Dorothea and Isabella, were both pregnant.
Geffrey left his sister, Isabella, a quantity of silver – a bequest perhaps recognising her lamentable financial situation and the affection between the two siblings.
The lack of opportunities for women, especially those like Whitney, created difficulties to make money in early modern London.
Due to this, there exists the reasoning that since Whitney is a woman in print who uses her work to make money, many may have considered her to be a prostitute of sorts.
[6] Through her uncle’s contacts, Whitney built up contacts in the printing industry and began penning verse which was published, initially anonymously but later under her own name or initials, using the tropes in fashion at the time but subverting them from the traditional, socially-approved roles women and men were expected to play in relationships and society generally.
In 1567 Jones published a small collection of Whitney’s verse: The Copy of a letter, lately written in meeter, by a yonge Gentilwoman: to her vnconstant Louer.
This collection of four poems in the popular epistolary form deals with relationship issues and presents four very different and somewhat unconventional views of how men and women ought to behave as lovers which serve to emphasise what she apparently saw as the hypocrisy and unfairness prevalent in society.
This criticism of accepted norms is used again in “A Sweet Nosgay” published in 1573 but this time she is attacking the status of women generally, not just as lovers.
As she freely admits, she was inspired by Hugh Plat's Floures of Philosophie (1572), reworking some of his aphorisms on the themes of love, suffering, friendship, and depression with an added female perspective that many would call “proto-feminist”.
The collection closes with arguably her best known work – Wyll – which demonstrates not only her intimate knowledge of London at this period but also uses a popular trope of the mock will to make social comment.
[7] Furthermore, Whitney was the first writer, male or female, “to exhibit any concern for gender-based phrasing, a practice that took another four hundred years to catch on”.
in A Sweet Nosegay, "til some houshold cares mee tye, / My bookes and Pen I will apply," possibly suggesting that she sought a professional writing career to support her in an unmarried state.
Whitney's publisher, Richard Jones, was a prominent figure in the contemporary market for ballads, and his purchase of her manuscripts makes sense in this regard, even if little evidence of their relationship survives beyond the front matter to The Copy of a Letter (1567).
While a lot of her practices (familiar allusions, exaggerations, the ballad measure) were common for contemporary male authors of the mid-sixteenth century, as a woman she was quite the trendsetter (in both her epistles and mock testament).
In addition, her material contained controversial issues such as class-consciousness and political commentary as well as witty satire, and was made available to the upper and the middle class.