I'm with you. Pessimism and cynicism is underrated in certain circles. I wish there was more pessimism before the U.S. decided to invade Iraq (remember "slam dunk"?), before the TSA was formed, or before someone decided to make Grown Ups 2.

If anything, there's a problem with too much optimism in project management. If there isn't enough budget and schedule to let a project slip by 10%, then the answer shouldn't be "yes, if we're lucky". It should be "No, let's pick something with better margins." or "Yes, because even losing money on this is worth it for strategic reasons."