Steve brings up a quote that I’ve always liked: By definition, risk-takers often fail
Let’s look at it: if something has a 20% chance of failure, then it should fail 20% of the time. If it doesn’t, then you are not really embracing the risk.
Trying to avoid risk, in life or in business, is playing not to lose. By focusing on risk avoidance, you’re taking your eye of the goal. Sure, you won’t lose that often, but you won’t win very often either, and you certainly won’t win big. In a zero-sum game, that’s fine, but life is not zero-sum. Eventually, you’ll end up being overtaken by the guys who do win big, resulting in a very painful loss by a thousand cuts.
This doesn’t mean that you need to fail in order to win. What it means is that you have to acknowledge risk, and notice when the risk is starting to blow up. The real trick to failure is to make the failure cheap; this lets you absorb lots of failure in order to gain the win you really want. Get really good at this, and you can make the cost of failure cheaper then the cost of avoiding the risk in the first place!
How do you do this? Feedback. Just as a wheel bearing will start rattling before it seizes up, most risks have warning indicators that you can notice if you pay attention.
In software development, most serious risks are project management related (at least, that’s the way it looks to this guy in the trenches). This makes it astounding that the dominant methodologies (which are the waterfall-based ones) focus on risk avoidance. They have to: they don’t have tight enough feedback loops to allow for effective risk mitigation. By the time you notice a risk is blowing up, it’s already the size of Three Mile Island and rapidly heading towards Chernobyl.
Getting good at paying attention to the feedback loops takes time. It requires the project manager (and everyone else on the team!) to listen carefully for that suspicious rattle. But it’s worth it. Replacing a wheel bearing isn’t cheap, but replacing the entire drive train because the bearing seized up is an order of magnitude more expensive.
And remember the words of Lobsang Dibbler and the Way of the Scorpion: Sometimes you have to lose in order to win.