Have you ever watched the TV show Undercover Boss? The premise of the show is this: The CEO of a massive company, a person with a nice corner office, luxury cars, and the authority to hire and fire hundreds, decides to go undercover within their own organization. They trade their expensive suit for a company uniform, a hairnet, and a messy apron. These CEO’s give up the rights and privileges of their position to do the most difficult, and sometimes menial jobs. They might spend a day cleaning toilets, working a deep fryer, or trying to keep up on a fast-moving assembly line.
Why would they do this?
They do it for a single, powerful purpose: to connect with their people, to understand their struggles firsthand, and to ultimately win their trust to build a better company.
This is a powerful idea of willingly setting aside your rights, status, and privilege for the sake of a greater mission. But this idea is not a unique one. Two thousand years ago, the Apostle Paul lived out the same reality. As we have seen in our series through 1 Corinthians, the church in Corinth was obsessed with asserting their personal rights – their rights to follow certain leaders, their rights to sue each other, and their rights to eat certain foods, no matter how much it damaged another believer.
But as we turn to the second half of chapter 9, Paul is going to show them a more excellent way. Paul is going to use his own life as the ultimate “undercover” story to demonstrate that a Christian’s life must operate differently from the world. He reveals a very important truth that we need to hear today: To win the world for Christ, we must be flexible in our outreach but disciplined in our walk.
THE FIRST DISCIPLINE: OUTWARD FLEXIBILITY
Now Paul begins this section with a statement that would have been considered counter-cultural. In a Roman world obsessed with status, citizenship, and freedom, Paul says in verse 19: “Though I am free and belong to no one, I have made myself a slave to everyone, to win as many as possible.”
Let this sink in. Paul is the great Apostle of the Christian freedom who wrote in Galatians, “It is for freedom that Christ has set us free,” and in Romans, “There is now no condemnation for those who are in Christ Jesus. For the law of the Spirit of life has set you free from the law of sin and death.” But all of a sudden, he says that he has voluntarily put on the chains of a slave. The apostle Paul, who belonged to no one but Jesus Christ, placed himself under the authority of everyone else. Why?
To win as many people as possible to the Gospel. That is Paul’s goal. Now, the Greek verb “to win” appears five times in these few verses. This word is a business term; it is a merchant’s term. The word “to win” here means “to profit.” This indicates that Paul’s call to the Gospel ministry wasn’t just a casual weekend hobby. Paul’s Gospel ministry had a clear vision, strategy, understanding of the people, and a strong value proposition to gain the greatest profit, which was to profit and gain the souls of men and women to salvation in Jesus Christ.
For example, imagine you are a businessperson trying to win a major deal in a foreign country. If you want to get a deal done, what do you usually do? You do your homework and learn the language, culture, customs, and etiquette. You show courtesy and respect because that relationship is crucial for success. And Paul applies the same strategic wisdom to his mission for the Gospel. And this is his principle of “becoming all things to all people.”
And Paul goes on to list several things he would do.
First, he says in verse 20, “To the Jews I became like a Jew, to win the Jews.” This means when Paul was ministering in a synagogue or in a predominantly Jewish area, he willingly submitted himself to their customs. He would have eaten Kosher. He would have observed their Sabbath traditions and festivals. He would have reasoned with them from their own scriptures (which we know as the Old Testament), showing how Jesus was the fulfillment of all of their hopes for the Messiah. Paul didn’t do this because he believed these rules were necessary for salvation, but because he wanted to win the Jews to the Gospel.
Then he says in verse 20, “To those under the law I became like one under the law.” The one under the law refers to the Gentiles. When Paul was in cities like Athens or Corinth, he entered their world. Paul would eat in their homes, sharing meals that a strict Jew would never touch. He would walk through their marketplaces, observe their idols, and present the Gospel in a concept they could understand.
Then he continues, verse 22, “To the weak, I became weak.” And this is a reference to the problem of eating meat sacrificed to idols shown in chapter 8. The “strong” Christians were proud of their freedom to eat meat sacrificed to idols. However, Paul became weak in the sense that he restricted his freedom, so he would not cause someone to stumble in their faith.
But here is the thing. We have to be clear. Paul isn’t saying, “When in Rome, do as the Romans do.” He was not a spiritual chameleon who changed his core beliefs to fit his audience. That is not what is happening here. Notice what he said in verse 21: I became like one not having the law (though I am not free from God’s law but am under Christ’s law). Paul is under the law of Jesus Christ. Paul’s convictions, morality, and devotion were to the law of Jesus Christ. The Gospel message never changed. But his methods, his approach, his non-essential practices? He held those with an open hand, ready to adapt or abandon them at a moment’s notice if it meant building a bridge for the Gospel.
To win the world for Christ, we must be flexible in our outreach.
John Stott, a British theologian, described this kind of missional living as the practice of “double listening.” He wrote that Christians are called to be bridge-builders, and this requires to “listen humbly and believingly to the WORD of God, and... listen sensitively to the WORLD that God has sent us to serve.” Double listening means that we listen to the WORD of God and also listen to the WORLD that God sent us to serve. And Paul was a master at this. He listened carefully to God’s word that his messages were always faithful, and he listened so carefully to the world around him that his method was always relevant.
This means that Paul was aware of different people’s backgrounds, preferences, and struggles, and then tailored his approach to communicate the Gospel in a way that was relevant to them. Simply put, Paul was a student of people. Paul made a deliberate effort to learn their stories, values, and proclivities through listening, observing, and participating in their world. Paul studied his audience to make the Gospel accessible.
Now, the challenge is that sometimes, we can make the Gospel inaccessible to others. Sometimes, we take a self-centered approach to the Gospel, where (unlike Paul) we impose our cultural norms, preferences, or assumptions about what is appropriate. It is kind of like assuming what a neighbor needs, what WE think they should want.
Here's an example: Imagine your grandmother has a simple flip phone. It has physical buttons, and she knows exactly how to use it to make calls and view pictures of her grandkids. It’s perfect for her. Simple and effective. Now, for her birthday, you decide to surprise her with an upgrade. You get the latest, top-of-the-line smartphone, and you spend hours setting it up for her. You feel good that you brought her into the 21st century. But what have you actually done? From her perspective, you’ve given her a confusing puzzle. Now, to make a simple phone call, instead of pushing a simple button, she has to remember how to unlock the screen, find the right icon, navigate the contact list, and avoid accidentally video-calling someone.
Sometimes, when we share our faith, we can inadvertently do a similar thing by clinging to our own ways of thinking about faith, worship, or morality as the only way. We may assume that everyone should worship or engage with faith in the same way we do. Sometimes, we judge people based on their past. Sometimes, we don’t learn about the struggles, challenges, and stories of the people who are around us. We build walls instead of bridges. We use our preferences in music, politics, in the way we dress, in the way we talk, and in the way we look as a litmus test to keep people in or out.
But what Paul does, challenges us to lay down our own ways of doings things to become students of people, to see from their perspective, to learn their stories so that we can effectively present the Gospel and bring them to the knowledge of Jesus. To win the world for Jesus Christ, we must be flexible in our outreach, but disciplined in our walk.
THE SECOND DISCIPLINE: INWARD RIGIDITY
But here is the thing. This kind of radical freedom and flexibility needs to have a balance. And this brings us to the second thing necessary to win the world for Jesus Christ, and that is the non-negotiable discipline. You need discipline because you cannot have a flexible outreach without a firm core. Paul knew that his mission to win the world was directly and inseparably tied to his personal walk with God.
But you might ask, “What does my personal discipline and walk with God have anything to do with winning my neighbor to Jesus Christ?” Your personal discipline is your public witness. Your credibility as a messenger is tied to your character as a person. This is why, Paul, all of a sudden, shifts from talking about the flexible servant to the disciplined athlete. He knew his audience in Corinth would understand this imagery perfectly. Now, Corinth was a major center for the prestigious Isthmian Games, which were second only to the Olympic Games. During these Isthmian Games seasons, the streets and hillsides would have been filled with athletes in strict training for these events.
And Paul asks them a question that they all know the answer to. Verse 24: Do you not know that in a race all the runners run, but only one gets the prize? Run in such a way as to get the prize.
Think again about the Olympic athlete. The discipline they go through! They wake up at 4:00 AM to train. They live by a strict diet. They endure thousands of hours of practice. They do this because they know that their personal discipline is what will carry them across the finish line. And what Paul is trying to get at is that in the same way, our inward spiritual discipline is what makes our outward mission sustainable. John Piper says, ““Christianity is not a playground, it’s a battleground… It is a brutal… rugged, cross-carrying, life-losing, go-for-the-gold race to the finish line of faith, and the prize is Christ.”
This is the discipline that Paul followed. He says in verses 26-27- “Therefore I do not run like someone running aimlessly; I do not fight like a boxer beating the air. No, I strike a blow to my body and make it my slave so that after I have preached to others.” The Greek verb here for “strike a blow” is a very visual one. In Greek, this word (strike a blow) literally means to “hit someone under the eye and give them a black eye.” And Paul says, ‘This is how focused I am.’ This is how hard I train. This is how disciplined I am. I am in a constant fight with my own sinful nature–pride, laziness, fleshly desires– and I am determined to win. I give my own selfish desires a spiritual black eye to keep them in submission.
Why did he do this? He gives his reasoning at the very end: “so that after I have preached to others, I myself will not be disqualified for the prize.” The great Paul, after all his missionary journeys, after all of his sufferings, and planting all these churches, lived with a fear that if he became spiritually lazy, he could be disqualified. This is not about salvation, but rather being disqualified from receiving his reward and from hearing, “Well done.” He knew that his outward mission was only strong as his inward discipline. The balance is everything. To win the world for Christ, we must be flexible in our outreach but disciplined in our walk.
CONCLUSION: POWERHOUSE OF DEVOTION
Church, we are left with these two powerful lessons for the Christian life. One the one hand, we are called to be like an undercover boss–flexible, empathetic, and willing to become all things to all people to build bridges for the Gospel. On the other hand, we are called to be like an Olympic athlete–disciplined, focused, and self-controlled, training ourselves to win an eternal prize.
J. I. Packer studied the lives of the Puritans in the 16th and 17th centuries. Packer wrote that the Puritan ethic was a “single-minded blend of the contemplative and the active.” Packer said that the Puritans were not men of the cloister (which means like an isolated group), but they were men of the marketplace. He said, “Their private world of devotion was the powerhouse for their public world of work and witness.”
That’s it. That’s the powerhouse. The inward discipline of prayer, of time in the Word of God, saying no to sin is the very engine that powers our outreach. It’s the disciplined relationship with God that gives us the strength, wisdom, and love to engage with the world. So, the question for us today is, “Are you pursuing both?”
Where in your life does God need you to be more gracious, flexible, and empathetic?
And where in your life does God need you to be more rigorous, focused, and athletic?
Church, let’s be a people who are serious about our faith. Let’s train with purpose. Let’s run this race of faith to win. But let’s do it with a flexible and open heart, so that by all possible means, we might save some. To win the world for Christ, let’s be flexible in our outreach but disciplined in our walk.
