One of my favorite sayings is "never compare yourself to others, for it will make you both vain and bitter. There will always be someone worse than you, and always someone better."
Ive always felt quite the opposite: comparing myself to those better off than me motivates me and to those worse off makes me grateful for what I have. This started pretty immediately after I entered the workforce. I don't know what accounts for me ending up on the win-win side of the coin, but I'm evidence that you can't take for granted that the lose-lose situation you describe will happen.
It's probably more accurate to say that it's a quadrant with the axes being 'comparison' and 'gratitude'. Being high on gratitude and high on comparison accounts for your quadrant of possibilities. It seems like the moral is to either be lower in comparison, or higher in gratitude. Or both :)
