I wonder if the winning game becomes your own boss and tiny companies. I want to do the jump, but lack of courage, good ideas, sales skills and a very good salary still holding me back (open for suggestions). But if the very good salary would go away, the scales tip instantly.
That was always the "winning game". Only problem is that's a lot of work. The more things change, the more they stay the same; if you want more money, work harder. People who don't want to work harder complain that other people make more money because they either don't understand or are in denial about the amount of work the people they envy put in. Yes there are exceptions. No pointing out exceptions won't help you,…
The elephant in the room is health insurance. We have a system where even if you have a fairly good income, buying insurance as an individual (or as a small company that isn't buying in a volume high enough for insurance companies to want to give you a discount) means that you'll in all likelihood be paying a lot more for a lot less coverage. The ACA attempted to solve this by having insurance companies offer plans on "public exchanges" by state and then subsidizing the costs, but because most people making good money get insurance through a job with benefits rather than buying it directly, in practice there aren't really any options on the public exchanges calibrated for people with high incomes. (Plus, if you live in a red state, they've likely refused to take the subsidies, which means either the prices are higher or the plans are even more meager based on what the insurance companies expect people without benefits through employment to be able to afford, or both).