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 :)

I saw this on a television show (don't remember which one), but a father was scolding his child who was complaining about another child having more candy or something.

He said: "The only time you look in your neighbor's bowl is to make sure that they have enough. You don't look in your neighbor's bowl to see if you have as much as them."

That was on Louie.

Example: Comparing engineering salaries :/. It can be addictive and disheartening to look up salaries and see giant numbers.

Perhaps I’m unusual, but other people earning more than me doesn’t dishearten me. My first job after uni was UK national average for all adults, so I felt well off even on “only” £24k in 2007, but ever since then, no matter how much I get paid, other people keep telling me I don’t earn enough.

If anything, the idea of earning twice as much feels weird rather than aspirational.

Perhaps some of them also meant you don't earn enough in the sense that they feel you're worth more than what you're being paid, which can be a reasonable belief.

But I suppose that in of itself can be unhealthy if taken too far.

This happens with me and I’m not proud of it.

I make a pretty healthy salary working in the valley, certainly higher than most. But of course there are plenty people that make more. When I see these I get that brief sense of negative emotion.

I don’t like it but not sure how to control it either. Except I guess not look up engineering salaries.