Should I work on software through my company for Playboy Enterprises?

Yes, you may. Your question has been multiplied a thousand times a thousand different ways by professional predicaments Christians encounter. There are a few simple principles to remember. First, Naaman’s job had a similar predicament, for he had to accompany the king of Syria into the pagan temple of Rimmon and bow with him there (II Kgs 5:18-19). What did Elisha say, “Go in peace.” Second, Paul assured us that though fornication is not to be tolerated in the church, yet we must work with fornicators in the world (I Cor 5:9-11). Third, there is all the difference in the world between providing a legitimate service to a pagan company or customer and joining that pagan company or customer in their sinful activities. You may own a hotel, even if half the rooms are rented for fornication, if you do not assist or promote that aspect of your business. Your lawn care business may keep the grounds of the local Roman Catholic church, as long as you do nothing to expose yourself to its false doctrine or promote it to others. As a doctor, you must tend to patients believing all kinds of heresies and guilty of all kinds of personal sins.

See Also

Christian ethics – case studies: Christian Ethics – Case Studies.
Christian ethics – principles: Principles of Christian Ethics.
Christian ethics – table of principles: Christian Ethics – Table of Principles