From Norman F. Dixon's On the Psychology of Military Incompetence -- “There are grounds for thinking that incompetent commanders tend to be those in whom the need to avoid failure exceeds the urge to succeed.” “... the person who fears failure prefers tasks which are either very easy or very difficult. If they are easy he is unlikely to fail; if very difficult then the disgrace attaching will be small, for no one really expected him to win.”
Dixon suggests Major General William Elphinstone's disastrous retreat from Kabul in 1842 as a case of someone “attempting tasks so difficult that no one expects one to succeed; hence little disgrace attaches to failure.” And he attributes Lieutenant-General Arthur Percival's disastrous failure to defend Singapore against the Japanese in 1942 to his trying “to avoid the unpleasant consequences of failure by not really trying.”
It's easy enough in retrospect to say how risk-averse somebody should have been: these may well be unfair verdicts on these particular officers. But if we do accept Dixon's verdicts, are there writerly equivalents?
One advantage writers have over generals is that, as Robert Cormier said, “The beautiful part of writing is that you don’t have to get it right the first time, unlike, say, a brain surgeon.” Again I recall Beckett's "To be an artist is to fail, as no other dare fail."
If all novels are failures by definition anyway, is Bolaño right that novelists are struggling “against that something, that something that terrifies us all, that something that cows us and spurs us on, amid blood and mortal wounds and stench?" Or are we rather avoiding disgrace by "attempting tasks so difficult that no one expects one to succeed?"
“Not any self-control or self-limitation for the sake of specific ends, but rather a carefree letting go of oneself; not caution, but rather a wise blindness; not working to acquire silent, slowly increasing possessions, but rather a continuous squandering of all perishable values.” — Rilke, who went to military school for a while. Doubt he would have made a good officer though.
I love how you are able to derive questions about writing even from books on military psychology :))
A bit tangentially: in Russia, a writer who is perceived of failure is commonly accused of suffering from a medical condition, graphomania. http://en.wikipedia.org/wiki/Graphomania (There's a funny Kundera quote in the article — so I suppose this condition is not endemic to Russia alone).