Those of us who work in technical areas like to believe that because we are engaging in technical endeavors rather than social endeavors, our work is defined and predictable. This hints that we know the future. I think Scott Adams captured the thought well:
We should not be so cocky. While the technical world is more structured and predictable than other areas, it has its limits too. One can only see so far down into complexity before predictability is lost in the detail. That’s where we get so called “Heisenbugs”. Looking out to the future we can only see so far as well.
Recently I’ve been reading The Black Swan. It is a useful reminder that the future isn’t as linear and predictable as we’d like to pretend it is. One idea that has stuck in my head is the idea that in order to take something into account that one will know in the future in one’s predictions, one must already know it. There is an inherent limit to how far we can see.
How is this relevant to distribution developers? Each time we set off to develop a new release, we make an assessment of how to best expend the available resources (our own, our company’s, our group of people we can talk into doing stuff) to make things “better”. We do the best we can, but we must always be mindful of the fact that we press forward using our best engineering judgement, but as we look into the future, eventually this is all just liquor and guessing too.
ScottK might have something to say ... 
Well, I kind of get it, but in my experience, it’s never been the engineers pretending that they can predict the future or how long and how many people it will take them to solve all the undiscovered problems and fulfill the incomplete and uncommitted requirements. That’s usually been a requirement placed on us by upper manager and (interestingly enough) Marketing. Then the work gets doubled and the time, people and resources get quartered. We explain that we cannot predict the future and that the unknown is called ‘the unknown’ for a reason and we get confused responses. Ultimately we make up numbers that we hope will give use enough to work with after it get pruned. This could lead one to make assumptions about the mental capabilities of those who don’t understand why the magical engineers cannot predict the future.
I originally thought your Dilbert was a bit smug. Perhaps I judged too soon. Or we need more liquor in the lab.
I’ve seen both in my career. I agree your version is more common, but it’s not just about trying to predict the future. It’s also about assuming the future will be like the past (e.g. no one will ever need more than 640K of RAM). Technical people are quite ept at assuming their experiences to date are adequate to inform them about what the future will bring.