In Seneca’s works, the interconnectedness between wisdom, morality, and happiness is the basic path for developing the peace of mind. Exercising wisdom is intrinsically linked to the expression of wisdom. Wisdom is the only way to find lasting happiness. There are three important limitations in Seneca’s philosophy. Firstly, an “action-driven consistency” does not necessarily require an “axiological consistency” (between virtues). Secondly, profit maximization could give birth to organizational fears: the fear to overestimate the realm of the superfluous (and thus to reduce profit maximization efforts) and the fear to lose organizational power, social status, and rank. Business decision-makers may experience both fears. Thirdly, any confusion between pity with compassion could misguide decision-makers about the most generous and prudent ways to help people. Two basic antecedents of a value crisis must be carefully analyzed: a legalistic positioning in matters of ethical issues, and the strategy of “setting an example”, regardless of the consequences for vulnerable individuals. When corporate reputation is prioritized, then any other ethical concern could be completely disregarded. Prudence, compassion, open-mindedness, and discernment allow decision-makers to identify optimal solutions to a value crisis.