Improving the human condition is assumed to require the acquisition of something humanity lacks. However, what if this assumption is wrong. What if improving humanity necessitates removing something already embedded within, the association of happiness with wealth and power. In both Boethius’s work, The Consolation of Philosophy, and in Shakespeare’s tragic play, King Lear, humanity’s predisposition to falsely associate happiness with wealth and power is revealed. Boethius and Shakespeare both show that this pursuance of wealth and power results in dehumanized individuals. Boethius focuses on the individual who seeks these desires. He sees this dehumanized state as the result of individuals falling short of their call to divinity. Shakespeare focuses on the power and wealth seeking individual’s active repression of the human dignity in others. In both works, seeking power and wealth diminishes an individual or individuals to a subhuman state.