Failure (or why we choose this path)
There was a great post by Aaron Hillegass back in December about his choice to start his own business, and how that led to failure (and what he thinks about it). Go read it, then come back and I'll give you my thoughts...
... well go on.
I completely agree that we get too complacent in that upper success range, although I would set the upper limit lower, closer to 85%. I haven't been able to put my finger directly on why I left my steady, well-paying job to do this, but that was a big part of it. I felt like I couldn't really fail. I was given tasks, and when those failed, it wasn't my fault. I was told the company had gone a different direction and that I had done well, but they needed me to do something else. Of course, the fact that there was nothing else to do at the time had a big hand in shaping my thoughts toward leaving.
What really hit me in Aaron's post, however, was that I would never be happy in a position that allowed me to succeed regardless of the task. I left work at the university for many reasons, but I had never considered that part of it was because there was no risk. I couldn't get fired there by anything shy of striking a co-worker. When I went to private industry (it was a state school), perhaps I was seeking out a more pressing environment, something that would challenge my talents and push me down into the "probable" success range, but not definite. Now that I'm working for myself, I find that I look for projects that are going to be difficult, ones that could produce nothing more than portfolio padding. Yes I do take the occasional bank-account-padding contract, but those aren't what I seek out (they have a way of finding me).
So we'll see where this goes, I'm hoping that I set the bar high enough this time, because I'm not sure where to go from here. (And I kind of like that.)