When I first met my friend Carol close to 18 years ago, she began mentoring me on the joys, pitfalls and basics of home schooling. Her advice, guidance and example were absolutely invaluable. After a few years, the friendship became deeper and more reciprocal. We helped each other, less mentoring and more holding one another accountable.

One afternoon I got a call from Carol. She asked me how much I loved her – she always asks me that before broaching a difficult subject. This day it was on the manner of … my clothing. Not how I dressed all the time, she had only one concern with one outfit in particular. Now I’m a pretty modest dresser, plus I am not a well-endowed woman so my clothes usually don’t reveal anything where on other, more curvaceous women the same outfits might. But on the previous Sunday, something stood out to Carol as being too revealing. And she told me so. She told me so.

As I sat with the phone up against my ear I could feel my cheeks get hot against my knuckles. Excuse me?! She quietly but firmly explained and I went through a litany of arguments in my head. Offended. Disgusted. Embarrassed. Unbelieving. (Me, not Carol.)

Ultimately, the Holy Spirit impressed on me the rightness of her call. Carol’s concern was for others in the church – especially for the young women I regularly mentor. Carol had obviously been thinking about this, praying about how to say it, even agonizing over the fact of whether or not she should. Her approach left me with no doubt that she loved me. With her heart on a platter for me to see as a gift or smash with a hammer she spoke what I needed to hear.

I chose to take the gift.

Not all women – even godly women – know how to rightly speak words of truth to others, including a very close friend. There is so much potential baggage, hurts and vulnerabilities tied to confronting. But love can bring the most uncomfortable situations to a place of understanding, even to a place of being better than before. That kind of true friendship – and mentoring relationship – is worth cultivating.


In the book of Philemon, Paul confronts this brother in the Lord in a similar way. There is love, pleading, genuine care as to how the issue at hand will affect everyone. It’s a very personal letter that opens a whole new window into the world of mentoring – a mentor-turned-friend turning back to mentor so that the one being confronted can, in turn, become an effective mentor as well.




I. Read Philemon 1-7.

The first thing to note about this tiny book of Philemon is that it is intensely personal. This letter is filled with transparent revelations, humility, an undisguised need for relationship, and insights into the very heart of this man of God that’s more open than anything else Paul wrote. And Paul had a vital message to Philemon on behalf of a young slave who’d become a spiritual son to him.

But more than just a message about a slave, Paul is putting himself on the same plane – a prisoner of Jesus Christ. Even in Paul’s greeting he uses that exact terminology. Now realize that Paul was indeed in a physical prison – most likely a dungeon. But J. Vernon McGee notes that here Paul was not saying he was in prison because he preached about Jesus. Greek is a versatile language with which a writer is able to have precise nuances in every sentence. Paul is saying specifically that he is a prisoner of Christ.1 In His chains, a bond slave to Him. We’ll discover why this distinction is important throughout the week.

1. Who is with Paul at the time of this writing?
2. The local church met in Philemon’s house, according to verse 2. Read 1 Corinthians 16:19 and Colossians 4:15 for other examples of house churches. Because of this, to whom else is the letter addressed and who are they, most likely?
3. Read Romans 1:1; Ephesians 3:1, 4:1, 6:19-20; Philippians 1:1; Colossians 1:7, 4:7, 12, 18. As you examine these other references to Paul’s chains, imprisonment, and being a bond-servant what differences or similarities do you see?
4. When Paul says he hears of Philemon, to what is he referring according to verse 5 and what does it show?
5. There is benefit for Paul’s journey to Christ likeness to have Philemon in his life. His approach is that of an equal, a friend. What are some of the phrases Paul uses to convey this relationship and the effect Philemon has from verse 6 and 7?



DAYS 2 and 3

I. Read Philemon 8-15; Genesis 45:5, 8; Acts 28:30; Romans 8:28-30.

In opening up his home during his arrest, Paul was welcoming each and every one who wanted to come. In Paul’s typical style of ministry – befitting his role as bond slave – he talked to people about the gospel, encouraged them in the Lord, shared Scriptures, and discussed Christ’s current work. One of those who came was Onesimus, a runaway slave. His master was Philemon. Now, Paul desires for Philemon to make a choice, but to make it on his own without being forced. This will take sensitivity and insight.

1. What are some of the expressions and styles of approach the apostle uses that might seem a little out of character for him?
2. What is the expression Paul uses in verse 10 to show his deep love of Onesimus?
3. Since the name “Onesimus” means “useful,” how does Paul use a play on words to explain to Philemon Onesimus’ changed character?
4. The power a master had over his slave was absolute. Whipping, being branded with iron, or most likely death were the normal punishments in the Roman Empire for runaway slaves.2 Harboring a slave was a capitol offense.3 How does Paul take a risk in verse 12 and what does he call Onesimus?
5. Why did Paul want to keep Onesimus with him? (verses 13-14)
6. How does the story of Joseph in Genesis and the Romans verses mesh with Philemon 15?


II. Read Philemon 16-17; John 8:31-36; Galatians 3:27-29; 4:1-4, 8.

It’s worthy to note that Paul is not seeking to end the entire slave issue right here, right now. In Colossians 4:1 we see that owning slaves was not uncommon in the young church of Colossae, or in any other city of the Roman Empire. Most of the new converts under Paul were Gentiles who had grown up under the political ideology of the Caesars.

But here there is a different emphasis. In his letter to the Galatians, Paul points out that when we are in Christ, we are now all equal heirs of the Father. Paul specifically says that being a Jew or Greek (our cultural and religious background), being male or female (our standing by birth), or being slave or free (our caste position chosen by man’s economic and political whims), doesn’t matter anymore. Being in Christ means unity and brotherhood. Dealing with this dilemma faced by Philemon and Onesimus on behalf of the young church’s future dynamics is extremely important.

Yet, in addition to equality in Christ, there is another issue. True slavery at its most insidious level isn’t physical, but spiritual.

1. What does Paul direct Philemon to do regarding Onesimus in Philemon 16 and 17?
2. According to the John 8 passage, where is true freedom found? Who are slaves and why?
3. Who is the one who remains “in the house”?
4. In the Galatians 4 passage, in what ways does Paul use the theme of slavery to illustrate a believer’s character and choices?
5. What are some of those things that keep people in bondage today?


III. Read Exodus 21:1-6; Deuteronomy 15:12-17; Amos 2:6, 8:6.

Ultimately, the issue of spiritual slavery is really the only issue. For there are only two choices, spiritually speaking: be a slave to sin by default, or a bond slave to the Lord Jesus Christ by choice. Both Philemon and Onesimus were now free and fellow heirs through Christ. Now Paul is asking Philemon to take a new step in maturity. As the older believer, Philemon needs to be an example to Onesimus.

In the Old Testament there is a provision for any Israelite who sold himself to his kinsman in order to pay debts. After 7 years of service, as part of God’s plan for liberation, the day came when that person was allowed to go free. If at that time the bond servant decided that his life under that master was preferable – maybe acquiring a wife, having children, having established a home and security – and he loved his master, he could choose instead to make the position of bond servant permanent. To seal the covenant, the master and bond servant would go to the door of the house where the master would pierce the ear of the bond slave, forever sealing him as part of the household.

This provision in Jewish law paints a powerful and beautiful picture. Choosing to be a follower of Christ means you are now His bond slave. When a person accepts Jesus’ sacrifice as the payment for sin and His resurrection as the fulfillment of the promise to live forever with Him, the seal of the Holy Spirit is immediate. But it takes time for a believer to mature. Coming to the point of complete submission is often not immediate. However, in the midst of struggle, there will be evidence of a willing heart.

A willing heart is one that remembers going to the Master’s door and what that commitment means. Daily. Intentionally.

A friend of mine observed that when God asks you to say “yes” to something extremely hard, that is the very thing that will reap the greatest blessing when you do. Philemon had to say “yes” to things unheard of in that day. Issues in the balance were things like what to do with Onesimus, how will the relationship with him be different, whether or not he should be freed, what kind of unifying standards will be set for the growing diversity of believers, how to incorporate God’s heart into an unjust system, and more. Would Philemon listen to the Holy Spirit through Paul and intentionally choose to model obedience?

1. In what position would Philemon be placing himself? How do you think his life might be different?
2. As you discovered in Day 1 of this week’s lesson, Paul chose to be Christ’s bond slave and it truly changed him. Think back to the day you made the decision to go to God’s door and commit all to Him. How has it changed you?
3. Choosing to become a bond servant in the Old Testament context left a visual reminder of that choice. What can you point to that visually shows your standing in Christ?
4. How could you use this illustration to help in a mentoring situation?



DAYS 4 and 5

I. Read Philemon 18-19; Romans 16:22; 1 Corinthians 16:21; Galatians 6:11 and 2 Thessalonians 3:17.

When confronting important issues, it’s never easy to temper passion with mature explanation and godly persuasion. You wonder how many drafts it would have taken Paul to compose this letter if not for the intervening inspiration of the Holy Spirit. Now that Paul has laid before Philemon the heart of what was at stake, he makes a pledge to go along with his plea for Onesimus.

1. The phrase “charge that to my account” in verse 18 is the definition of the Greek word “imputed.” Along with Philemon 17 and 2 Corinthians 5:21, what does Paul’s statement illustrate?
2. He could have used others as well, but who was Paul’s scribe, named as such in scripture? List some of the circumstances where Paul would deviate from this method of letter writing.
3. Why do you think it was so important for Philemon to see Paul’s handwriting in verse 19?
4. What does it imply when Paul says that Philemon owes him his life?


II. Read Philemon 20-25.

If Paul were sitting next to Philemon speaking to him face to face, I have no doubt that by this point in the conversation Paul would be leaning closer to Philemon, placing a hand earnestly and firmly on his friend’s arm in emphasis. Deep respect coupled with a sense of brotherly love causes the apostle to let down his guard even more and drive his point home.

1. Philemon 7 features the same word as verse 20 – “refresh.” Read Matthew 11:28, Mark 6:31 and 1 Peter 4:14 which all use the same word translated as “rest.” What does this imply about Paul’s request to Philemon?
2. In Philemon 21, Paul was encouraging Philemon to do the right thing. Look for the word “obedience” in Romans 1:5, 6:16 and 16:19, 26; 2 Corinthians 10:5-6 and 1 Peter 1:22. What is Paul asking Philemon to be obedient to?
3. From Philippians 1:25-26 we know that Paul was anticipating release from prison soon. Paul’s intent was to then visit the family (Philemon 22) – and, hopefully, an alive and well Onesimus. Read John 10:10. How would Philemon’s acceptance of Onesimus according to all that Paul asks illustrate the heart of Christ in this verse?


III. Read Psalm 5:7-8, 11-12, 37:3-11, 84:8-12, 86:1-10, 130:7.

Paul is essentially calling Philemon to mentoring. He’s passing the torch with Onesimus and gently giving his friend some advice. Philemon has a lot of influence both in the church held in his home and probably the community at large. Most likely he has other slaves. And he has a son, Archippus. What will Philemon choose? Will it be the standards of the Roman Empire, or will it be the heart of Christ?

So much in the Psalms relates to obedience and the resulting rest that comes from finding answers and refuge in the Lord. When Paul opens his heart to Philemon, he does it with complete trust in the God who guides them both. Speaking the truth lovingly and faithfully can result in a much closer relationship between believers – and a greater dependency on God by both parties.

1. As you meditate on these verses from Psalms, think of Philemon – and yourself – coming to the place of faithful obedience that provides rest for all fellow bond slaves. What might this look like for you?
2. Who has God put in your life this week to encourage? To whom will you give rest by speaking the truth in love?



My example at the beginning of this week’s study pales in importance next to the topic Philemon needed to wrestle with. But speaking the truth in love, in any circumstance, is difficult and is perhaps the number one reason more people don’t feel equipped to mentor. We all carry too much baggage. We all cringe at the idea of retaliation from someone who might lash out, pointing out faults of our own. We all want to preserve our own skins, our own feelings, and our own sense of security. It’s time to put self aside. Too many younger women are following dangerous paths from which they might be diverted through a firm word and loving heart. This study is named “Intentional” for a reason. Investing in the life of another is intimidating and will not happen effectively without a mind set for the job. Paul didn’t always see the result he wanted and was shunned by many – we’ll see that more in 2 Timothy. He did it anyway. The resulting life change in those who did listen was worth it.



1. McGee, J. Vernon. Thru The Bible with J. Vernon McGee, Volume V. Thomas Nelson Publishers. Nashville. 1983. Page 498.

2. “The Roman Empire In The First Century.”

3. Bradley, Keith. “Resisting Slavery in Ancient Rome.”


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