When we use the term “Pharisee” in everyday English, it already has won a new meaning. According to the dictionary, it’s secondary definition is:
a self-righteous person; a hypocrite
Now there are many believers who have some (if not all) pharasaical traits. One thing common with them in the Bible narratives is their pursuit of righteousness on their own terms. They might understand that it is God that does all the saving with their minds, but with their pride-filled hearts, they can’t get used to the idea that they will be entirely dependent on someone else for them to be right and eventually be indebted to that person.
Pride doesn’t flow well with that.
So, they find ways to get what they need their way. It’s obvious in the Bible, especially in this story. Such pharisaic people usually ask:
“Teacher, what good thing shall I do that I may obtain eternal life?”
Mat 19:16 (NASB)
They’re only concerned of continued blessings from this life to the next. No pain. All gain. And you can see that in his answer to Jesus, when he claims to have held onto all the necessary requirements to get into heaven:
“All these things I have kept; what am I still lacking?”
Mat 19:20 (NASB)
This young man seems sure he already made it and we must assume his last question was merely rhetorical rather than sincere (based on his final reaction). People like this don’t believe they lack anything in their faith and they’ve made it into this closed circle of the “elite” – those chosen to enter eternal life.
Hence, to his dismay, Jesus put a final requirement (v.21) and it had nothing to do with his wealth nor his ability to let go of his possessions. He left sad (v.22), because his self-built righteousness was torn into pieces. His perception of what it took to go to heaven was demolished in an instance. This assurance of salvation took a toll on him and left this “Pharisee” heavily wounded.
Nothing can hurt or offend a “Pharisee” more than challenging his believed state of salvation, because that’s all they have. They rest on their own righteousness and not on the Rock and things usually get messy when someone starts shaking on their little “sandcastles” (Mat. 7:24-27).
Btw, you can’t attack a true disciple of Christ by questioning his salvation. Either he would react as the tax collector and beat his chest in repentance to seek true salvation (Luk. 18:13) or he would react like Paul who is so mature he cares more about the salvation of others rather than his own (Rom. 9:3).