So how did Chaucer make a living? He was a servant of the crown: he worked in customs (his family were established and important wine-importers) and in what you might call public works. He was attached to at least one important diplomatic mission. He had family connections above his status, which are still a little murky. He was, for a medieval person, remarkably “class-mobile.” A hard man to place. But he held a good position under Richard II, and, when Richard was deposed and murdered, held exactly the same place under the usurper, Henry IV. (You can read all about this in Shakespeare, by the way, if you don't care about getting the details quite right.)
You can argue all day – in fact, for several scholarly lifetimes – about whether he wrote poems “to order” for, say, Richard or John a Gaunt. I'm inclined to think so, but we'll never know. But in any case, one thing he did not do, and which would never have occurred to him in a million years, was hawk his poems on the street. For one thing, there was no one on the street who could afford to buy a book of poems: in the days before printing, the making of books required not only expensive materials – parchment is not cheap, and vellum is downright expensive – but weeks of painstaking work, by a literate person with writing materials, to produce a single copy. The resulting object sold for (I'm making a number up, because these equivalencies are always impossible to nail down, but I'm confident I'm in the ball park) something like $500 in modern American money. A book of poems, in other words, was a luxury item, like a sculpture or a painting. Ordinary people didn't have them. Chaucer's library of almost 300 volumes represented a small fortune, and must have consumed most of his disposable income.
So a poet before the advent of printing was nothing remotely like a modern novelist, writing to please a faceless public. Chaucer and his ilk composed for an audience of a few wealthy patrons, or really, often, an audience of one. Written poetry used to be a very intimate art. We tend to assume that this was a bad thing, and to picture crass lords making the sensitive poets write interminably about fox-hunts and tournaments, but I think often it was very fruitful. So quirky and personal a poem as the Book of the Duchess would never have been written for a mass audience.
And what of Richard II and Henry IV? What were their motives, in this relationship? Chaucer seems to have been an able man, useful to have around – he supervised the construction of a grand tournament arena, among other things – but most likely for them he was primarily a prestige object. It was like having Michelangelo or Leonardo on the payroll, for an Italian prince. England was beginning to come out of the eclipse that followed the Conquest, and its Norman upper class was abandoning French and coming to a new identity. They wanted a national literature of their own. The English, like the Romans before them, were playing catch-up. They were, often quite self-consciously, working to build up a canon, based on what they knew of Classical literature. There would have to be epics and tragedies and comedies and satires, they knew that. They would have to find verse-forms that could rival the Latin hexameters in power and flexibility. There would have to be an English Virgil, an English Seneca, an English Terence, an English Horace. (One of the odd things about this emulation, for us, is that we no longer admire some of these poets very much. But the rediscovery of Greek literature was still to come: all the medieval poets had to look to was the – to our minds often lackluster – imitations of the Romans.)
Up until the shattering advent of Wordsworth, this was the game English poets were playing. It became somewhat more complex as time went by, as other European literatures made claims – never undisputed – to have achieved classical status, and as Greek literature was recovered and translated. But few people seem to have doubted the project. The basic plan of the temple of literature had been laid down in classical times, and the job of English poets was to build it again in English (and Christian) stone.