Wow, I would freak out if my T didn't let me talk about "someday." I think that not preparing you for "someday" leaves you much more vulnerable to both abandonment and loss because, healthy or not, no one can predict the future. Your T may have no intentions of retiring or dying but I think your T does you a disservice by discouraging any discussion about what life might be like without him. It's true that we will always have things we can learn about ourselves or work on, but if your T is the only person you ever feel safe with, or the only person you ever feel comfortable enough with to talk about problems, the loss will be magnified greatly if his plans to outlive you or to never retire don't quite work out the way he expects them to. In my opinion, facing your fears of loss and abandonment, and working through them in therapy, is a much healthier choice than feeding into your T's apparent belief that he has so much control over his life and his fate that he can predict his future and yours also.