CNNMoney.com has an interesting piece on Steve Jobs' recent Apple stock and options dealings. It not only shows that Jobs didn't artificially manipulate or inflate his worth, it shows he did the exact opposite: make financially unenlightened decisions that literally cost him piles of money (over a billion in personal wealth by the article's estimates).
But the thing I thought was most interesting in the article was this insight:
Though Jobs is considered one of Silicon Valley's leading egomaniacs, which is saying something, he had virtually no faith in his own abilities. When he wrote us that letter, he knew something the rest of the world didn't: that in a few months he would stand on a stage and introduce a new product called the iPod. Yet he not only insisted his options were worthless but put his money where his mouth was two years later and made a trade that will be immortalized as one of the worst ever.
It has been proven time and again that some, if not most, of the most successful and innovative leaders have, ironically, relatively little confidence in their future success. I think it may very well be this same lack of confidence that helps them to be so successful. The overly confident are prone to overlooking significant risks and/or challenges and often fail to adequately plan for contingencies. Intelligent leaders who feel they are on the brink of failure tend to make their plans much more robust, helping to gird up their chances of success even when their chances may already be quite high.
So, to those would-be entrepreneurs and innovators out there, don't ever stop being paranoid about failure. Comfort is a luxury you simply can't afford (at least not until you've exercised those options and diversified your portfolio).
