I don't normally re-read books, but Taleb's "Fooled By Randomness":http://www.amazon.com/gp/product/0812975219/sr=8-1/qid=1152054792/ref=pd_bbs_1/104-6084284-1316768?ie=UTF8 is well worth a second look. I'm only 30 pages in, but something hit me square on the head last night.
I'm sure you won't disagree when I say that life is a single path out of many possible paths. On top of that, much of your life is influenced by forces out of your control - chance. Consider two paths that I could take right now.
# A full time, steady, software development job.
# Software Entrepreneur.
Regardless of which path taken, I will be influenced by chance with either extremes of tremendous luck, or grave misfortune. When you layer chance over the two possible paths, the middle 95% paths will look like so:

* 1a: Very lucky in full time work.
* 1b: Very unlucky in full time work.
* 2a: Very lucky as an Entrepreneur.
* 2b: Very unlucky as an Entrepreneur.
The job path will provide the most stability, and certainty. This is because risk has been traded off. But, this leads to a severe limit on your up side, but a nice safety net on your down side.
The entrepreneur paths show us there is a massive range of outcomes. Either turn out mega rich, or scrape by. What hit me last night is how hugely dispropportianate the up side is for an entrepreneur. Suddenly what seems unrealistic is not only plausible, but likely.
Call it naive if you like - but I won't.