Unlike Phillips' illustrious predecessors in American art, such as Benjamin West of Philadelphia and John Singleton Copley of Boston, Phillips lived and worked not in established city centers, but new territories opening up throughout New England and the Mid-Atlantic. Though he was able to successfully market his skills from a young age, it's likely that the relatively sparse demand for painted portraits, a luxury good, was the main factor necessitating an itinerant career that saw the artist move regularly, family perhaps in tow, between western Massachusetts, Connecticut, and the Hudson River Valley. The artist moved on as he exhausted the demand of the local community for painted "likenesses". This wandering lifestyle is archetypically Romantic, rather contrasting with the bourgeois domesticity of his portraits, which are almost always set within interiors. A letter from the American artist John Vanderlyn to his nephew, John Vanderlyn, Jr., from Kingston, New York, dated September 9, 1825, stated, "Were I to begin life again, I should not hesitate to follow this plan, that is, to paint portraits cheap and slight, for the mass of folks can't judge of the merits of a well finished picture, I am more and more persuaded of this. Indeed, moving about through the country as Phillips did and probably still does, must be an agreeable way of passing ones time. I saw four of his works at Jacobus Hardenburgh's the other day painted a year or two ago, which seemed to satisfy them." Such comments from a well established academic painter such as Vanderlyn positions Phillips not as a wandering peddler of art, but instead as an artist with social and economic importance. This is also visible in his clientele, which consisted of judges, doctors and business owners.