Visualizing failure: good or bad?

Here's an interesting thesis put forward by Dave Winer in a blog post entitled "Dan Gillmor’s story":

I’ve learned, through both successful and failed startups that the only times I’ve been successful was when I couldn’t visualize failure. ... The times that I have visualized failure, I did fail. The times I couldn’t, I didn’t. Hardly proof, but still a belief of mine.

Hmmm... is there something to that?

It may be true, but Mr. Winer evaded the heart of Adam Green's thesis (in a blog post entitled "Dan Gillmor shares the lessons of Bayosphere"), which is that we need to consider the possibility of failure. That's not to say that we should obsess over it or try to force ourselves to construct artificial failure scenarios, but it is to say that if we haven't even considered the potential downside risks, we may be leaving ourselves open to risks we may not be willing and able to cope with should they arise. Even Mr. Winer actually acknowledges some of this when he says:

I remember trying to imagine what the last day at Living Videotext would look like, and I just couldn’t imagine it. I knew the day would likely come, but I didn’t see how I could lock the door for the last time, calling it a failure.

See, there, he did consider failure, and that was enough to verify that his gut feeling was worth relying on and that he should move on with confidence.

I'm sure there must be plenty of people out there who can offer personal stories on whether considering or not considering the potential for failure was a help or a hindrance or maybe a complete red herring.

-- Jack Krupansky