It's a combination of things in various levels, but it all boils down to the stigmatizing of mistakes.
1.
It's true the world doesn't owe you anything, but it can actually TAKE AWAY damn near anything with the slightest provocation. Since the establishment of America as a global superpower and not just a fledgling nation (basically around WWI believe it or not), we've done a pretty good job at innovating ways to make life more and more predictable and implementing fail-safes to prevent catastrophic collapses. And yes, welfare is part of it because the welfare system was created in response to The Great Depression. People might argue about it now, as they did then, but most of those people weren't saved from starvation because of it; the people who were have a different take on the issue. Either way, as the decades went on and technology and politics started shifting to make society even more stable--our violent crime rate is the lowest it's been in over a century--the result is that we've become more hypersensitive to things when they go wrong.
2.
Making matters worse, our traditional practice of sensitivity from 1800-1999 was "Walk it off, crybaby" which was a sentiment prevalent among the status quo...if you WEREN'T part of the status quo, then every aspect of the social, cultural, and legal system that protected people from life's misfortunes had an exception clause at the bottom of the page with a box marked "Woman/Nigger/******"; if you fit one of those 3 categories, then you didn't qualify for those protections. When the "Women/Nigger/******" demographics finally got numerous enough to stand up for themselves, they ensured that the legal system didn't allow for such preferential judgments about whom the rules applied to. Unfortunately, this set a precedent that all people are corrupt and shiftless without the shackles of bureaucracy holding them on the straight and narrow.
Basically every politician prior to 1968 according to Hippies.
3.
The Protestant Work Ethic essentially established the idea that constant work and busyness is a sign of a morally focused person. As a result, material prosperity became associated with good character. In real life, a multi-millionaire could have built his fortune on the backs of child slaves in Third World sweatshops and illegal tax shelters, but as long as he can afford to shave and pay taxes, he'll be perceived as more virtuous than a scruffy 20-something who dropped out of college to volunteer in the Peace Corps and ride his bike between soup kitchens to maintain a carbon footprint of 0.5. This was bad enough in the effect it had on the arts as a sustainable career move, but when Ayn Rand and her Manifesto-As-Novel philosophy of Objectivism established Oligarchy as the sign of heroic capitalism, it became the religion of Wall Street sociopaths for generations, and currently inspires the belief that anyone who isn't an investment banker is a parasitic socialist.
The Great American Hero.
4.
For all of their obsession with innovation and advancement, Americans are pretty convinced that social stuff stays the same. When the academic system was built, people were pretty sure that the 18th-century model would be the template in perpetuity, and the employment arrangements based on accomplishment would remain intact forever. That ended in the 1950s when economic prosperity flourished to the point where a college education was a skeleton key to a living wage in a stable workforce. With reasonable tuition prices, post-war college attendance skyrocketed, and people worked their asses off to get their diplomas. The result of such a massive upswing in enrollment--and graduations--created an "academic inflation": with more people in the workforce qualifying for a finite number of positions, employers had to increase the required credentials just to filter out the applicants. Cut to 2014, and a job once requiring a BA now needs a Masters, and a job once requiring a Masters now needs a PhD, and jobs requiring PhD's are full at the moment, but McDonald's is always hiring. Nobody anticipated this, and nobody has any idea how to fix it because it would require gutting and rebuilding the entire credential system from stem to stern.
What do these 4 things have to do with each other? Well, if you combine 1) a society increasingly accustomed to an automated society where nothing goes wrong, 2) a culture of legislation where everything is liable for something, 3) an added emphasis on wealth being a reflection of character, and 4) an unbelievably competitive academic system where only the 1% of the 1% stand a decent chance...
...Then you have a society where accidents no longer exist, everybody is susceptible to crushing legal action, and only people with flawless performance records are considered the exemplar of success, which is the only virtue.
Oh, and one more thing...
5.
As #1-4 progressed, technology had to develop in order to facilitate their respective goals. The busier life got, the more profit could be derived from labor saving devices and combinatorial technologies. The result: more innovation in communications and data transfer systems in 20 years than all technological advancements over the last century. With this stuff, there was no limit to how busy people could stay, no limit to how much work they could do, and best of all, no time too early to get people started using them.
The Kindergarten thesis paper is the most important one you'll ever write.
All 5 of these things create a society where patience is obsolete and everything must be done perfectly on the first try in order to be considered eligible for a life that doesn't involve selling blood on days off from the restaurant.
And as I've said before, when the self-esteem movement came about, they realized that there were better ways to motivate children to learn than beating them like pack mules when they fucked up, but failed to adjust the system to allow more autonomy for them so that accomplishments actually meant something. So instead, they championed the cause of celebrating mundane tasks that preserved parental supervision and micromanagement, and dissuaded children from real-life experience of doing things for themselves.
As a result, you have at least 2.5 generations (with more to come) of people who have had everything done for them to protect their entrance acceptance scores from the permanent taint of mistakes, and a society that trains and conditions them that everything is to be done fast and with little effort. Couple that with a culture loaded with technology that keeps them constantly stimulated and interconnected, and you have a society of people who have never experienced impulse control beyond 10 seconds. Neurological studies have shown that instant gratification wires the brain in a way that increases information processing, but atrophies creative thinking because it relies on accessing information sources rather than cognitively extrapolating a theoretical answer. A study conducted with American and Chinese elementary students showed that American students gave up on a problem within 15 minutes if it couldn't be solved while the Chinese students worked until the clock was stopped: we've been conditioning people that things are supposed to be doe quickly and if they can't, then you should quit and move on to the thing you can get done fast. In our obsession with efficiency and return volumes, we dissuade people from putting effort into anything.
And with that massive level of interconnectivity, you have hundreds of millions of people hanging out in the same digital space trying to make themselves noticed without any experience in defining themselves outside of other people's opinions. And without any idea of how to do things for themselves.
So of course you have people with massive entitlement: the world taught them to shut off their brain and let other people do shit for them.
All ages and walks of life. I owe them a job. I owe them all their benefits. I owe them overtime. It's never ending.
