Contrary to the current narrative in our culture that blames people for being successful and explains it away as this shadowy "patriarchy", "white privilege" or "male privilege", the real reason some experience a delicious way of life in the UpperTier is a lot easier to explain.
Yes, some successful people inherit wealth but most simply make wiser choices than the masses. If you do that one thing repeatedly, guess what happens? You eventually enter the UpperTier. It's not rocket science. Its hard work yes...but hard work going against the mainstream approach to life. You cannot simply be the best bean counter at your company and expect to eventually be free from the need to work. The game does not work that way. If you approach life and finances in the same way that the other 95% of people do then why on earth would you think that you will not live your existence in the 95% pack that work until the end of their days for 2 or 3 weeks a year in vacations and who get excited over a 5% pay raise.
I met with a friend for lunch yesterday and he reminded me of this iconic video. This was at near the beginning of the story of a man that decided that society's boxes simply could not contain him...or his products. This central view of his became the foundation of this company while he single-handedly transformed the music industry, the cell phone industry, and of course personal computers. Of course he had help rowing the boat but he steered the ship.
I invite you to take a similar view to your career and finances. If the thought of slaving for the next 20 years trading your time for money does not inspire you...then maybe this will...
So tragic to see that his legacy became the very monolith that he lived his life in defiance of. Before Jobs was such a success and became so phenomenally wealthy, look at his mindset. In the video at 1:24...and his response was to suggest to pay for half of the ad PERSONALLY in defiance of the board's opinion. Now that is swagger. Now that gets you ahead in life.