After his waterman apprenticeship he served (1596) in the fleet of the Earl of Essex, and participated in the Capture of Cádiz in that year, and in a voyage to the island of Flores in the Azores in 1597.

[3] He became a member of the ruling oligarchy of the guild, serving as its clerk; it is mainly through his writings that history is familiar with the watermen's disputes of 1641–42, in which an attempt was made to democratize the leadership of the Company.

[4] He also addresses the coachmen, in his tract An Arrant Thief (1622); recent development of horse-drawn carriages with spring suspension, and use of them for hire on land, had taken much trade away from the watermen.

Sylvester, Beaumont, Sir John Harrington, Forgetfulness their works would over run But that in paper they immortally Do live in spite of death, and cannot die.

An example is his 1621 work Taylor's Motto, which included a list of then-current card games and diversions: The prodigall's estate, like to a flux, The Mercer, Draper, and the Silkman sucks: The Tailor, Millainer, Dogs, Drabs, and Dice, Trey-trip, or Passage, or the Most-at-thrice.

At Irish, Tick tackle, Doublets, Draughts, or Cheese, He flings his money free with carelessnesse: At Novum, Mainchance, Mischance (chuse ye which), At One-and-Thirty, or at Poor-and-Rich, Ruffe, Slam, Trump, Whisk, Hole, Sant, New Cut.

He achieved notoriety by a series of eccentric journeys: for example, he travelled from London to Queenborough in a paper boat with two stockfish tied to canes for oars, described in "The Praise of Hemp-Seed",[5] which was re-enacted in 2006.

He had more than sixteen hundred subscribers to The Pennylesse Pilgrimage; or, the Moneylesse Perambulation of John Taylor, alias the Kings Magesties Water-Poet; How He TRAVAILED on Foot from London to Edenborough in Scotland, Not Carrying any Money To or Fro, Neither Begging, Borrowing, or Asking Meate, Drinke, or Lodging, published in 1618.

By wondrous accident perchance one may Grope out a needle in a load of hay; And though a white crow be exceeding rare, A blind man may (by fortune) catch a hare.

Taylor ferried himself between the educated elite and the urban working class, bridging a gap in early modern readership that valued quality over quantity.

Despite failing to enter fully into the world of London's literary elite, Taylor developed a sense of authorial personality which survives his work, and may have been the genesis of the "celebrity" of author, as he carefully crafted his public image throughout his career, beginning with his reworking of his otherwise frowned-upon occupation as a waterman into a name for himself as the King's "Water-Poet".

[14] Taylor provided a style of writing that was not bound by the constructs of classical learning, as most poets of the time would have been products of their grammar school education, whether they intended it or not.

[2] He entertained no gout, no ache he felt, The air was good and temperate where he dwelt; While mavisses and sweet-tongued nightingales Did chant him roundelays and madrigals.