My outlook is far more positive than yours. Human knowledge and progress build upon themselves and are cumulative. Free societies and free markets that encourage individual choice and initiative and independent thought and entrepreneurship have a decisive competitive edge in improving living conditions and the happiness of the people involved in them. Sure there may be wars and other setbacks, but progress does occur.
In the case of the United States (and more broadly "western civilization"), the past century has seen exponential gains in technology and medicine and standards of living and individual opportunities that have far eclipsed anything in all of previous human history. Alternate political systems such as Communism and Fascism have proven themselves comparative failures. Alternate ideological systems (such as militant Islam) that strike out at us in their frustration are in the process of getting their asses kicked because of our overwhelming superiority.
Our civilization is far from perfect. In this country we could be so much freer, politically and economically, than we presently are. There are bad trends intertwined with the good. But I would not care to have been born in any earlier period of history or in any other country. And I am even more hopeful about the future and the wondrous possibilities it promises than I am about the present.
So yes, it is my opinion that good choices tend to result in good outcomes and become self-reinforcing. And that this is indeed the lesson of history.
Your outlook could be more positive, or your historic eyesight could just be shorter.
I am not of the opinion that our civilization is any better (in the sense of 'goodness') than the Roman civilization. Yet the dark ages came between then and now when all that goodness was lost. It was lost because of the 'yitzar harah' or 'evil inclination' of man. We forget the reasons we want to do good and start to behave in selfish, self-destructive ways. There have been other great civilizations in history before the Roman, yet all have come to the same end. Over time we tend toward the bad without some external influence.
The Roman civilization took over 500 years to fall. Western civilization has been at it for close to that long now. And IMO we are headed in the same direction. Of course, it doesn't look like that from many of the material metrics. But Rome didn't look like it was about to fall either - right up until the "moment" it did.
You are right about the wonderful technology we have today, but we have no ethics to help us deal with it. Do you remember the promise of TV when it was brand new? (I remember when TV was brand new.) How about the promise of electric appliances and the freedom they would bring. What about the utopia of the French Revolution? The Russian Revolution? The Chinese Revolution? All have failed to live up to their potential, and the pace at which new ideas lead to destruction has only increased as our technology has increased. How long did it take for the Great Society to create a permanently poor underclass by destroying the family?
I could go on, but the examples are not important. The concept at the base is important. Choice is a result of human will. Human will is not a random variable. And the human will tends toward destruction.
There is an answer. Technology is not it.
Shalom.