What might contextualization look like for us?
First, we must identify, as much as Scripture allows, with the people we are trying to reach. A good illustration is when Paul circumcised Timothy in order that he would be not become an obstacle to bringing the gospel to Jews (Acts 16:1-5).
Second, we must realize that such identification requires that we forsake our Christian rights/freedoms in order to become a servant to all. We must ask ourselves if we are willing to forsake our personal musical tastes for the sake of the gospel. What of our personal clothing choices? Maybe even our eating habits? It all depends on whom we are seeking to reach.
In other words, any musical worship style may be permissible for you or me under the blanket of Christian liberty, but if our freedoms and liberties cause another to stumble, then it would be sin. For instance, if your worship service is heavy metal style, it may be attractive to some unbelievers, but to the believer in your congregation who has come out of the rock/drug/party culture and into the purity of the body of Christ, heavy metal music during a Sunday morning worship service could very well be a stumbling block. We must be responsible to one another.
Put another way, by missiologist Davids Sills:
Some mistakenly believe that contextualization means making Christianity look just like the culture. However, contextualization is simply the process of making the gospel understood. . . . In fact, much of what many call contextualization is simply an effort to be trendy or edgy..., but that is not contextualization; that is marketing.
And here is Dr. Don Carson’s message on 1 Corinthians 9:23-27, from The Gospel Coalition 2009 National Conference.