I can point to a few instances in my life where I know the Holy Spirit has prompted me to do things I wouldn't rationally do. However, I don't know if the Holy Spirit guides me every day. Maybe it does. Maybe it prompts me to say things in conversations I wouldn't normally say. Maybe it stalls me in what I'm doing so I'll be able to help someone that wouldn't have been there if I had left five minutes earlier.
The Holy Spirit is a mystery. Training ourselves isn't. We can do the latter while always being sensitive to the former. Maybe in the process we'll naturally begin to listen to the Holy Spirit and not even realize it. May all the glory be to God.
I can recall two times that I have totally ignored the Holy Spirit. Both produced nothing. One was when I bailed a friend out of jail. I kept feeling that I should give him the money and tell him that freeing him to be the person God wants him to be is similar to this. I thought it was corny and I wanted to keep my $275. He never became a Christian, nor did he ever repay me the money. I don't know if my actions would've changed anything, but I do feel that I missed an opportunity led by the spirit on that one. God wanted him to hear that message and I failed to be the messenger. I followed my logic and did what I naturally would've done rather than the extraordinary thing God would want me to.
The other time was on one of the spring break trips to Mexico. During one of the services during their open mic (without the electronic mic) time, I felt prompted to go up to the front and say something I felt was very corny. I would've just brushed it off but later that night I was talking with another member of our group. He shared with me that he felt he should've said something at the service earlier in the day. It was the same thing. And it was never said. I wonder how many people said no to saying it.
Both examples seem to have been God prompting me to do something I wouldn't normally do. In both I failed. I pray that I won't ignore the Holy Spirit's promptings ever again.