What a person has is of no consequence, whether much or little, when it comes to the deep satisfaction of the soul. Apart from Christ, the rich and beautiful, and the poor and unlovely, will all end up in precisely the same misery.
Legalism is when we try to obtain the result of obedience by our own means and strength. It is self-righteousness, as opposed to God's righteousness covering us, and the two are as different as spirit and flesh.
The harsh reality is that my flesh must die not so much because of what it does, but because of what it is.