"He punishes himself for failure."

Disagree. In many cases academia DOES actively punish failure, through negative feedback mechanisms involving grades, comments on papers/essays and the like that subjugate "out-of-the-box-thinking" in favor of a certain theme or buzzword a professor wants to hear, what his or her political or economic viewpoint is, etc.

I'm not saying this is inherently good or bad either. If you're a surgeon or an airline pilot, your room for experimentation & outside the box thinking is slim to nil. But actively discouraging an aspiring hacker, developer, entrepreneur etc. from experimentation (I.E. a high rate of failure before success) is a surefire way to diffuse the creative process, in my mind.