1. You are most certainly not obnoxious, nor are you wrong to expect to have your full 50 mins. If he does that on a regular basis (i.e. he is late & lets you go early) then please bring it up. It is not acceptable for him not only to not apologise but, worse, to cut your time short.

2. That depends on the therapist’s approach/therapeutic ‘leanings’: some will probe and/or initiate conversations, whereas others will adamantly let clients take the lead and wait accordingly.

Still, there are some things you might try: could you ask him to help you out in starting the conversation or to bring up topics? Could you write some issues (bullet points) and bring them up? It would still be best for you to take the plunge, however hard it is. As you rightly pointed out, you pay for it so make the best use of the time that you can.

3. Usually there is a plan as in, they ask what issue brings you in and typically, you (both) will work on this. Obviously, other issues might crop up and the work can take a detour but i find this unusual that he claims not to know where to go next... What is his background?

4. Can he help you with interview preparation? Maybe role-play it (as if he were the interviewer) and work on your anxiety etc.? He needs to give you the ‘tools’ and in a progressive fashion before setting you off in the big bad world...

Finally, I wouldn't say that you are failing at therapy but maybe either he is not the right match for you or his technique/therapy modality is not suitable.