It is reported that on several occasions he sent a telegram to his wife Frances from an incorrect location, writing such things as "Am in Market Harborough. He was allowed (and encouraged) to improvise on the scripts.This allowed his talks to maintain an intimate character, as did the decision to allow his wife and secretary to sit with him during his broadcasts.
He had planned to become an artist, and his writing shows a vision that clothed abstract ideas in concrete and memorable images.
Even his fiction contained carefully concealed parables.
Father Brown is perpetually correcting the incorrect vision of the bewildered folks at the scene of the crime and wandering off at the end with the criminal to exercise his priestly role of recognition and repentance.
For example, in the story "The Flying Stars", Father Brown entreats the character Flambeau to give up his life of crime: "There is still youth and honour and humour in you; don't fancy they will last in that trade.
Chesterton's writing has been seen by some analysts as combining two earlier strands in English literature. Another is represented by Oscar Wilde and George Bernard Shaw, whom Chesterton knew well: satirists and social commentators following in the tradition of Samuel Butler, vigorously wielding paradox as a weapon against complacent acceptance of the conventional view of things.
Chesterton's style and thinking were all his own, however, and his conclusions were often opposed to those of Oscar Wilde and George Bernard Shaw.
Chesterton's writings consistently displayed wit and a sense of humour.
He employed paradox, while making serious comments on the world, government, politics, economics, philosophy, theology and many other topics.
In 1902 the Daily News gave him a weekly opinion column, followed in 1905 by a weekly column in The Illustrated London News, for which he continued to write for the next thirty years.
Early on Chesterton showed a great interest in and talent for art.