Recently my son tried out for a travel basketball team in our town. He has played travel basketball for two years and our town is a very competitive sports town. Even though he is good at the sport, I had discussions with him on how competitive it would be and what would happen if he did not make the team. The team had twice as many kids try out as open spots and he did not wind up making it. I was surprised and disappointed but he handled it very well (better than me) which I think had to do with discussing expectations earlier.
This is also extremely important in our jobs as we have many stakeholders with different levels of expectations. We need to manage them in terms of cost, schedule, quality and risks so that as things arise they are not seen as surprises. For example, when deploying a new product or technology we should set expectations that there will likely be fallout and that we should be prepared for that. This is much better than assuming no problems and then being surprised (and even worse, not prepared) when things do happen.
So the key is understanding expectations and managing them as appropriate. I should have done that myself and expected that a competitive sports town cares only about winning!