Pseudo-sociological trend pieces are a dime a dozen these days, but a recent one called Why Generation Y Yuppies Are Unhappy stands out because it's apparently been the center of much intergenerational debate on social media. I found it interesting because many of the critiques of "Generation Y" are similar to those used against previous generations such as "hippies" and "slackers" (and also just about anyone who questions the status quo).
To set up the argument, author Tim Urban constructs a strawman caricature called Lucy who's a member of Generation Y, "the generation born between the late 1970s and the mid 1990s. She's also part of a yuppie culture that makes up a large portion of Gen Y." Given that the middleclass has been in decline for some time now, I'm not sure why anyone would think yuppie culture makes up a "large portion" of Gen Y. He even created a pejorative acronym for people like Lucy: "Gen Y Protagonists & Special Yuppies, or GYPSYs. A GYPSY is a unique brand of yuppie, one who thinks they are the main character of a very special story." The reason for the unhappiness is reduced to an equation: Happiness=Reality-Expectations
Though overly reductionist, the equation makes sense because one can increase happiness by raising one's reality or reducing expectations. However, like most people who support the status quo and/or get all their information from corporate sources, Tim mostly focuses on why Lucy needs to lower expectations because to raise reality would take collective action and systemic change (and no, "picking yourself up by the bootstraps" is not enough). It's much easier to condemn the individual with typical attacks leveled against young people and idealists who voice grievances: you're overly ambitious, you think you're special, and you have a faulty perception of the world.
To be fair, he seems to be trying to describe not an entire generation, but a specific type of person of the generation (perhaps an annoying coworker?). However, at a time when tuition rates and student debt are at an all time high and so many people just out of college are unemployed, underemployed, or stuck in unfulfilling dead-end jobs they're overqualified for, it's easy to see why such an article might strike a collective nerve. And funny pictures with trite platitudes like "The current world is bubbling with opportunity for an ambitious person to find flowery, fulfilling success" or "You can become special by working really hard for a long time", won't make them feel any better.
There are countless better explanations for rising levels of unhappiness and discontent not just among Generation Y, but for 99% of the country. The biggest factors are explained succinctly in the videos below: