I dont have a clue what your upbringing looked like, but even up to around age of 25, I never ever expected nor was told to expect any of that. The success despite all that is much sweeter.
Maybe thats some US thing, being raised in eastern Europe you were born to shit, you were considered insignificant shit and that was about it. Thats what being occupied for 4 decades by russians causes to society, on top of other bad stuff they are so natural with.
Maybe stop telling kids how they are all special and great and all will be astronauts and let them figure it all out by themselves? Teenagers being frustrated that they wont be owning some posh expensive house, thats pretty fucked up upbringing and life goals to be polite, thats not success in life in any meaningful way.
I recommend checking biggest regrets of dying people, focus on careers and money hoarding are consistently at the top.