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I agree with that notion very much. All good programmers I know are pessimistic in their design and implementation. It's not about having no hope of success - it's about imagining everything that can go wrong, assume it will, and finally make failure impossible by design. Assume all your input will be garbage, your hardware will be insufficient, your users will be total idiots, and fellow developers are nitwits that will break your code at the first opportunity. Then rule everything out systematically, by thorough planning, user involvement, unit tests, documentation, defensive programming. Management will hate you, still. MBA types thrive on ignoring details and being extremely optimistic ;)