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."
