The playing field has never been level and never will be. In fact if you live in the States right now the financial field is most the lopsided it has ever been in the history of the country. People have good reason to be discontent. In the last decade they watched their networths decline significantly, they either lost their job, can't find one or are working longer hours with more responsibility for less money. They are also burdened with inflation costs of health care, elder care and literally everything across the board when their real wages stay flat.
Yet we should tell them that everything is OK because they have potential to succeed and if they do fail it is largely their fault? It is insulting to quote this American dream scripture to people and expect them to stomach it when they see the cold hard facts of reality. The mantra is to keep up the illusion because it keeps everyone sedated. Just telling someone Gee you know how hard it was in the civil war is largely useless. Why not go all the way back and say "Hey buddy at least you don't have stone wheels and have to worry about getting eaten by a sabre tooth tiger. Boy they had it really bad so I better be happy."
What really happened is the system failed, individuals failed, but most importantly people got fukked by those who were smarter than them and they were taught to like it. If you need any evidence of this go look at any of the available data on happiness indexes over the last 50-60 years. They all show a significant decrease in overall happiness despite economic advances. Even better go look at the political parties in the states. They are all one in the same. Keep up that illusion of choice. Your vote sure makes a difference! It is a comedy of gigantic proportions.
And by in large the rich emerged unscathed from all this because there is no economic situation that they can't withstand. They simply have the capital to manage risk well. Even those people that were fraudulent, including corporations, prepared by paying off the political system. The layman simply has no chance when faced with an economic downturn and black swans. Bailout money to whom indeed.
I do concede that in the long run the country will largely be fine. All the apocalyptic rhetoric is annoying but so is the naive attitude that your life has no limits. I would argue that the world has very real limits whether you acknowledge them or not. There are societal limits,family limits, economic limits, educational limits. If you take two twins of equal talent and ability but placed them in different environments; one in a "poor" environment (and all that entails) and one in a "rich" environment (and all that entails) there is going to be a vast gulf between how they turn out. You are running a race with a corvette and a go cart expecting them to finish at the same time.You might quote some odd case where this deviates but run it multiple times and a true picture free of the variance of life will emerge. The American system does not magically intervene to correct this inequality so stop believing the lie. You can't reach the commanding heights because those with power, influence and most importantly money keep moving the bar out of your grasp.
So where does that leave you? You should stop feeding into the system. Stop setting your expectations unrealistically high. Realize that everyone has a motivation for doing anything. Start thinking for yourself and realize how you are being manipulated everyday. Acknowledge that sometimes events happen outside of our control and there is nothing we can do about it. If you have gambled for any length of time you of all people should realize how luck factors into the equation. Life is no different.
Does that mean you should give up? No. Live your life, educate yourself financially so you can extract yourself from this modern economic slavery and use the tools against your masters. But most importantly call out these plutocrats for all the bullshit they spew. Foster dissent and live your life on your own terms not those you are taught to want. Think and live.
And for what it's worth Thoreau was a simplistic fruitcake who realized how his views sucked and moved back to society from Walden's pond when it hit him square in the face.