I'm wondering since you pose the question when your T will challenge you, if you feel there is something he is supposed to challenge you on?

Therapy isn't about being a "good client". Though, I can appreciate the want to do that! Therapy is about being workable. You can put the tough stuff out there, show your flaws or "bad side", and continue to work towards your goal.

I wonder if being a "good client" has masked some of the things needing to be worked on? Which would in turn, limit the amount of appropriate feedback a therapist can give. If my clients came to me, and acted the part of having it all together, I'd be a bit baffled on what to offer.

Utilize your time with T to get what you need. The challenging will come.

Good luck.