Think his point is pretty legit, no point putting on a happy face for someone, be true to yourself and thats all that matters (unless you have your own family to take care of.... then I guess you gotta )

If your a happy go lucky person then be the happiest person ever.

If your a dread in your own sorrow kind if guy, and happy not to make a change, then be as dreaded as you possibly can be.

The content feeling isn't the best state to be in, as its mostly a false security, as when you are content with something your senses turn dense and more venerable than ever.