Perhaps willing your estate to the state would be a way to resolve this hypocrisy? While you are alive you don't put yourself at a disadvantage and can act as an investment manager for your future donation to the government. Once you die, you will no longer have anything to lose by donating everything you have left to the government. Obviously if you have heirs it becomes a bit more complicated.

Having thought about this a bit more, the idea of "not being taxed enough" is not necessarily about raising revenue for the government. They don't need to take your money to tax you, they can just print money and tax everyone with inflation. The point of taxing the "rich" more is to level the playing field. It is prevent power from concentrating in people who are not democratically accountable. So in that case, donating your estate will not achieve that goal.