"Why would we need to experience the Comforter if our lives are already comfortable?"

Robin is my closest friend of more than 30 years. He's challenged me lots of times in lots of ways. Most recently, he asked this question of me and the rest of the staff at CCC: "Why would we need to experience the Comforter if our lives are already comfortable?" 
That question relates to a passage in John 16 where Jesus promises to send the Comforter, The Holy Spirit. I had never thought about it that way...why would Jesus promise that if we weren't going to need it? 
When my walk with Christ is comfortable, what does that do to faith? In my estimation, it eliminates the need for faith. At least in terms of dependance. I suppose I could reword the question as: Do I live by faith? 
I continue the query to myself with questions like: Do I follow Christ in such a way that, without God's intervention, it will fail miserably? Do I seek God's will every minute? Are my thoughts towards my life with Christ "comforted" because I have sought His guidance throughout?
That passage in John 16 says that The Comforter will convict the world of it's sin. Ironically, last night Theresa and I talked with a young lady who needed comfort because her God-centered lifestyle had convicted those around her. Subsequently, she was experiencing persecution. 
Maybe that's why we don't need comforted, we aren't living lives that are pure enough to convict the world of anything.
We, as Christ's disciples, watch and listen to the same trash as entertainment, use the same vulgarities, struggle with the same sins as people who have never heard of Jesus. We are comfortable in our own little sloppy pens as so many pigs, awaiting slaughter.
When I am trying to live like Christ, I need comfort. When I'm living like the devil, I don't. And there's no "fence-riding" in between the two.
The bottom line is, sin is fake comfort resulting in eternal discomfort.