((Betsey)) - I'm not sure I know what to say . . . I am amazed how you navigate through the issues, point out analogies, validate, and gingerly help him express himself!
The main thing I see (& remember I'm still new at this) is that he seems to wait for you to describe what he's doing, what he's thinking, and then he lets you know when you're "on the money" in the description. He lets you name his issues.
I liked the part of reminding him that he is a 'solutions guy' at work - that he does have the skills in another area of his life that could be applied here.
How many more analogies will it take til he rolls up his sleeves, opens his tool box of skills, and starts working?
Betsey, you are incredible! And an inspiration to us all...