The world has always worshipped success, even before Calvinists incorporated the idea into a creed. This “cult” of success teaches that if something succeeds, then it ought to succeed; its success is a proof of its inevitability, even its goodness. Thus, every fashion or fad, every ideology that enjoys triumph over minds or nations, takes on an invincibility it ought not to have, and a lustre it has not earned.
Chesterton saw this attitude as both illogical and dangerous, and would have none of it. He urged people to judge the world and themselves not by the way things are, but by the way they ought to be. One of the ways he did this was to challenge them in their view of history. For example, he questioned whether the defeat of Napoleon or of Robert E. Lee were good things in themselves. He suggested that a victorious Napoleon might have led to a united Christendom wherein the Great War would never have happened. With Lee, he mused that the agrarian (Distributist) South, left to work out its own problems and destiny, might have benefited the whole of mankind.
As he phrased it, the uncertainty of success leads to the certainty of free will, that just as we have, as individuals or nations, done things, we can also undo them, when they don’t work, and when they are wrong. Success as a cult, said Chesterton, was a sham, as unthinking as your average “successful” American millionaire.
And for further reading in Chesterton’s works, see especially, “The Fallacy of Success” in All Things Considered; “The Man on Top” in A Miscellany of Men; Heretics, chapter 8; What I Saw In America, especially “The American Business Man.”