"Think about it" means "I want you to think that:" means "I want to believe that:"

"... you don't have to go through the pain that you did learning through your previous experiences. I think there's easier and better ways out there. Life should be more enjoyable than just slogging away. So think about it, dig deep, don't be stubborn, be open, and enjoy yourself."

Being dissed like that hurts. Yes, it is a gloating underhanded diss. Translation of the above:

"You were wrong. You chose the hard way. You didn't listen. You were too 'stubborn' to change."

Well, I hope you're proven horribly wrong, you smug yuppie cosckucker. I hope your 'easier and better way' leads you to spend years in the wilderness with no option but to do the slogging that you try so hard to deny. I'll be there to tell you that you should be more 'open'.

"Or do ye think that ye shall enter the Garden of Bliss without such trials as came to those who passed away before you?" Koran 2:214