While I agree with what you said, I was reminded of Camus's Sisyphus. Bob was pushing the boulder. It's hard to infer whether he knew if the boulder would ever reach the top, but even so, the process was there—and because it was there, I think his friends were there too.
In my own circumstances, I'm actually holding onto programming by force. For most people, going down a different path would have paid better—I'm not a Silicon Valley person, after all. My environment isn't particularly favorable either. But even so, I love this life. Life is, in a way, a trial, and in a way, suffering. In Eastern thought, life is suffering.
If the whole of life is steeped in suffering anyway, then perhaps it's better to choose what you want to do. This is ultimately a difference in ways of thinking, and I suppose you'd agree there's no right answer in what I think either.
Having a dream that's hard to achieve can be cruel (though Bob might not have thought so), but without that cruelty, you would never have dreamed that dream in the first place. A dream is cruel not because it's hard to achieve, but because it makes you unable to give it up even when it isn't achieved. And for those who can't give it up, perhaps the very process of pushing that boulder is already life. In other words, the dream itself may have already become life.