The Last American Bagholder

Which way to Easy America?

Nobody ever told him that America was easy. In fact, he grew up among those who felt that America was challenging. Most of these people had already lost a game that he didn’t know he was playing. It was a game with endless possibilities and nobody was there to explain how it worked. His only clues were found in the bitterness and struggle of those who raised him.

Sometimes, he’d see another family’s winnings from the Great American Game, and that stuff seemed pretty good. Some of them had beach houses, vacations and the nicest cars. That was Easy America. As the eldest in a family of renters, single parents and welfare, Hard America was all he knew, but perhaps that could change that if he played the game correctly. If his version of America was going to be easier, he had to figure some things out.

From those around him and those on the news, he started to see that it was a rigged game, but he would play it the best he can. For he was motivated. The rules weren’t complex, and he’d encountered enough people to know that anyone could do well at it. He just needed to get more money, and then America would get easier. Simple.

He was decent enough at school to get some much-needed wisdom and skills. The young man got his first job at the age of 16, after he was rejected from working at the drug store at 15 for being too young. He worked under the table for cash shortly after he learned what taxes were. He was making progress.

Some of those mentors told him he needed a degree, or else he’d be stuck doing physical labor for his wages. They told him to take out debt to get this degree. That scared him, so he went a safer route. He pinched pennies at a community college, and kept that miserly mindset through his last two years at university. A college graduate. Neat. Did he make it to Easy America that quickly?

It would be many years later before he realized that these weren’t the kinds of colleges that guaranteed access into Easy America. That came from the kinds of schools that were much further away, and much more expensive. Also, nobody told him that he should have studied one of a handful of degrees that led directly into high-paying careers. So his humanities degree wouldn’t blow anyone away, but still, a college graduate!

That gets you something, right? Sort of.

The degree got him through his first few doors, but he would now need to string together a decade of momentum. Luckily he was able to do so, and by all standards he was ahead of where he thought he would be. He’d avoided every obstacle that slowed down his classmates. Student debt? None. Work experience? He had plenty. Nihilism? He was too busy for that.

But still, he wasn’t getting anywhere easily. Every step forward was hard-earned, and it always had a cost. Friendships faded. Hobbies were forgotten. Vices were adopted. Health was inconsistent at best. He was starting to doubt if it was all worth it.

He had more money, which told him that he was playing the game so well. But at the same time, so many others were playing an easier game and getting a helluva lot farther than him. Some even had trust funds, or high-paying jobs waiting for them at 22. It felt tiresome to compete with.

But the Great American Game is not always an enemy. Sometimes, it brings good fortune, and this man was ready to make the most of it.

Things got better in a short span of time. A better job was secured. A life partner was met. Finances got stable, for the first time in his life. He learned about the stock market, which was apparently a hobby for people living it up in Easy America. He understood why quickly, as his investments doubled in value in the span of a few months. He started thinking long term for the first time and it was both thrilling and terrifying.

Success was just a few months away. He was buying a home. This is what everyone told him was the ticket into Easy America. The effort paid off, even if he had seen it not pay off for so many people around him. Sometimes, he thought that he had earned it more than them. In reality, he got lucky and then he didn’t screw it up.

At least he didn’t screw it up yet. He’d heard stories about people who lost it all after achieving so much. The game giveth and it taketh away. He had to be careful. His time in Hard America made him paranoid and scared, like his house of cards could crumble at any moment.

He always believed that Easy America should be accessible to more people, but there wasn’t much he could do about that problem. No matter what he accomplished, it wasn’t going to improve the situation for anyone else. His kids, maybe, if he could just keep it up.

For that to happen, his 30-year mortgage would have to be paid off, and he’ll need to leverage his newfound equity to start a business, or improve his home. But this was all dependent on his home retaining its value. Otherwise, he’d be holding the bag on a heavy amount of debt for a home that his family could outgrow someday.

He also realized that he had been born at the wrong time. In 2015, his same home cost half as much as it did in 2024. Less than a decade earlier, his ticket into Easy America would have been much easier to achieve. The boundaries that separated Easy America from Hard America started to appear quite arbitrary.

Regardless, this man was now a rooting part in the system that created the two different types of America in the first place. He needed stability. He needed others to achieve what he had, but without devaluing his own achievements. At the edge of Easy America, the situation felt precarious. Maybe Easy America isn’t comfortable enough. Maybe he would need to keep striving for something even easier rather than help others get a ticket for themselves.

Millions of people like him will answer this question for years to come: Which way to Easy America?