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Willis built up his reputation in the public at a time when readers were interested in the personal lives of writers.
In his writings, he described the " high life " of the " Upper Ten Thousand ", a phrase he coined.
His travel writings in particular were popular for this reason as Willis was actually living the life he was describing and recommending to readers.
Even so, he manufactured a humble and modest persona, questioned his own literary merit, and purposely used titles, such as Pencillings by the Way and Dashes at Life With Free Pencil, which downplayed their own quality.
His informally toned editorials, which covered a variety of topics, were also very successful.
Using whimsicality and humor, he was purposely informal to allow his personality to show in his writing.
He addressed his readers personally, as if having a private conversation with them.
As he once wrote: " We would have you ... indulge us in our innocent egotism as if it were all whispered in your private ear and over our iced Margaux ".
When women poets were becoming popular in the 1850s, he emulated their style and focused on sentimental and moral subjects.

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