"I'll be honest. Everybody thinks you're cuckoo for cocoa puffs. You got a good church going on and you hit the eject button and now you're the international man of fu Manchu mystery," said Pastor Mark Driscoll of Mars Hill Church in Seattle.
"What is going on? What are you thinking?"
Chan announced in April that he would be letting go of Cornerstone Church in Simi Valley, California – a church he founded 16 years ago – to follow a stirring in his heart. He preached his last sermon there in May and has since been speaking to Christians and pastors alike about his restlessness with comfortable Christianity and his desire to surrender himself fully to God.
Responding to Driscoll during a frank discussion – that also included Pastor Joshua Harris of Gaithersburg, Maryland – about his decision, Chan said, "A lot of it is personal. A lot of it is when I look at the Scriptures I see this commitment, this devotion, this hardcore 'we will follow, we'll do anything, we're all about going out and making disciples.'"
He said he wanted to start over and get a core group of disciples who just try 100 per cent to follow the life he felt was clearly spelled out in Scripture.
"While I feel like I'm getting closer and closer to what the Spirit is leading me to do based on my convictions of Scripture, I don't think I can totally get there by constantly tweaking," he explained.
"I've read the Book. I got this theology in my head. I have all these thoughts and convictions. Let me just start something fresh with all of those convictions rather than constantly tweaking something that I may have possibly taken in the wrong direction for a little while."
Driscoll and Harris, who are council members of The Gospel Coalition, expressed some concern over starting something and leaving and wondered if he would repeat that pattern in the future.
"How long do you think you'll be at the new work before discontentment or frustration sets in because if I was in the core group I would ask that question. Is this a discontentedness in your soul that won't ever be satisfied?" the Mars Hill pastor asked.
Harris also offered, "If everybody out there just said 'hey, let me go start something new' ... that's an important thing to realise. We do need guys who are in an established church and go 'you know what, maybe it's not alright but here's how I can slowly over time build and redirect in certain ways and so on'."
While Chan cannot predict what will happen in the future, he said he doubts that he will go through what some see as a "crisis" again because he has felt this stirring since high school. He just never had the courage to say it out loud and to follow it.
"I don't know how to explain it other than there's always been this core conviction of 'something's not right and I think I know what it is but I'll just keep quiet'," he explained. "Now, I want to express it and live it and just go 'now, I believe I'm living in congruence with the whole New Testament'."
"Maybe I'm dreaming but I got to go for it."
He also stressed that his leaving Cornerstone was for the church's own good. "It's kind of diverting some of this 'I must hear from Francis'. By staying there, I was causing, not causing the whole problem but I wasn't helping the issue."
Driscoll questioned Chan on the theology behind some of his thinking to give everything up.
"It seems to me that if the primary view of sanctification comes through simplicity, poverty, suffering, if you don't get those things it's almost like when God blesses, it's hard to be sanctified because you don't know what to do with it," Driscoll said. "And so you almost have to get rid of that which is complicated, make life hurt a little more, go to a third world country, and/or adopt poverty and give it all away because you're only allowing God to sanctify in the preconceived ways.
"What if God wants to sanctify you through not poverty but generosity, not suffering but blessing, and what if it's not through simplicity but complexity?"
Driscoll cautioned that Chan could be following a "poverty theology", which he said is "the same error as prosperity theology – that holiness comes from have or have not, not who is".
Chan has experienced tremendous success with his books, including Crazy Love, and as a pastor and sought-after speaker. Cornerstone Church grew to be one of the largest churches in California.
He indicated that he could easily write a cheque for a new hospital.
While he agreed that what he's doing could become a pursuit of poverty, he said he does not believe it is that.
"I believe it's motivated by love and a desire to be Christ-like," he responded. "I don't want to suffer needlessly or just to suffer.
"To me, the core issue here has to be love," he said. "I think in times of prosperity, for me, I look at Scripture and go 'Wow, this is awesome. Look at this great selling book, all this money, what do I want to do? I want to give it to the people who need it.' I get excited about that.
"I get excited about becoming a picture of Christ. Of course I have the right to get the stuff that I want and enjoy it but it's again letting go of that, not holding on to that and saying here's an example, let me lay that down, and go and lay down my life for the brothers."
He added that living simply and being able to be generous is a dream come true for him and his wife.
"Gosh, here's all these people who are dying and in need. When I met them, that's when I fell in love with them and it actually was a joy to give. It's not like 'ah, I'm too rich God's going to get mad at me,'" he said.
And, "this is not like 'oh, Francis, such a martyr, he gives everything up,'" he added.
Four months after making the big announcement, Chan is still not certain what God is calling him to, though he has mentioned Los Angeles as the likely destination. He has mentioned that he plans to visit a third world country with his family to care for victims of the slave trade and orphans while spending time seeking the Lord.
What he does know is that there is pride in him that has destroyed him in many ways and he just wants to spend the next season of his life purifying that.
"I don't even know where I'm going to end up," he said. "Maybe there's more of a fog that I'm in than I realise."