This is explored to a degree in a pop psychology book by Daniel Gilbert called "Stumbling on Happiness". There are certainly better sources, such as the papers

This is explored to a degree in a pop psychology book by Daniel Gilbert called "Stumbling on Happiness". There are certainly better sources, such as the papers Gilbert uses as his primary sources, but the book is an accessible way to learn about the high degree to which our happiness depends on subjective interpretation of our self-comparison to others. There's a theory out there that we evaluate ourselves mostly against people we can reasonably consider our peers (e.g. college classmates or the kid who grew up down the street, not Barack Obama or Steve Jobs) because they are the best proxy for what our lives could have been like had we made different choices with the same starting point (e.g. medical school instead of starting a business). These peers represent our best experimental data given a world of singular outcomes. The double-edged sword of you achieving success is that those hundred or so people you compare yourself to sit high up on an asymptotic curve of outcomes. That is, if your peer group all has advanced degrees and decades of experience, the outcome-difference between the least and most successful will be extreme. "Low success" peer groups sit at the flatter part of the curve, so peers you compare yourself to will "look more like you", thus avoiding the unhappiness of comparative failure when you judge yourself. I'm forgetting whether this particular idea comes from Gilbert's book or another source, like perhaps "Status Anxiety" by Alain de Botton.