In my country we have a game show called "Deal Or No Deal", don't know if you've got a version of it in Canada. Basically a contestant selects random briefcases one after another, each containing an amount of money until their left with the final one. Every now and then the show will present them with a "bank offer" - a certain amount of money that they can take if they simply stop playing for the grand prize. As the game get closer to ending these offers get more and more tempting and the contestant has to choose between playing it safe for a moderate amount of money, or risking it all for a shot at a real big prize. More often then not, these amounts are in the tens of thousands of dollars.
So often you see these people really fretting over what choice to make when this happens as if their whole world hinges on them making the right choice. Quite often, these contestants have a partner or spouse sitting up on the stage in front of them and the partner/spouse shares in their anguish over what they should do. It makes me shake my head when I see those kind of people getting worked up over money like that and I think to myself, "you have a boyfriend/girlfriend/husband/wife there with you right now who you love and who loves you! If you walk out of that studio with just half a buck, you're still a hell of a lot richer then so many people out there." And I like to hope that even the rare couples who literally do walk out of that studio with just half a buck realize as they curl up in bed together that night that they really have done pretty damn well for themselves.
What I'm trying to say is that even if the problems/hardships that your boyfriend gets anxious about do come to pass, so long as he's got a loving girlfriend like you in his corner, he'll still be having a pretty good day. Especially if he talks about you so lovingly as you state in your other post.
I can't speak to what is actually going on between you two, but
possibly what happens when you address his problems is that he perceives it as some kind of dissatisfaction with him on your part, and maybe that scares him because he might think it's an omen of the end of your relationship.
I think perhaps the main thing you can do for him is just make it clear that you care about him and that you are there for him and that your feelings for him are stronger then any of the setbacks he might face. While you will understandably share in his sadness, disappointment or fear when life doesn't go his way, try to let him know that despite those setbacks, you are still overall happier to have him in your life then you would be if you had neither him nor his setback.
It will surely take some time, but once he realizes that you are by his side rain, hail or snow, he will hopefully begin to feel that even when other parts of life don't go well for him, things are going pretty sweet for him in general. And hopefully knowing that will make the "worst case scenarios" he faces seem less significant by comparison, which should significantly reduce his anxiety about life in general.
Even on the days he comes home with only half a buck, if he can curl up in bed with a woman he loves, he's doing pretty good.
I think it's great that you are trying to give him the freedom to make his own choices and mistakes. This is a real show of respect and support for him as he is and not a "him" that you want to turn him in to. Though I can appreciate how you find it difficult to not persuade him to make mistakes you fear will hurt him, because seeing him in pain hurts you, too. I hate to say it, but I think that these things are just something you'll have to whether. Failure, sometimes even certain failure is a part of life. Sometimes we have to do what we have to do even if we're sure to lose. Again, the most important thing is that you whether these setbacks together, rather then let them become a divisive force between you.
I can understand your distress at him trying to push you away. From what you've said, it sounds very much like it's him trying to spare you any suffering rather then a genuine desire for you to go away. Something you need to realize is that the sexism that is still prevalent in our "enlightened" 21st-century age comes into play here. In our culture, men are supposed to be the heroic ones and women are supposed to be the precious, vulnerable flowers that need us to shield them. We are groomed to believe that we've got to take the full brunt of anything charging towards us (and anything charging towards our women), and even mocked whenever the woman in our lives seems stronger, or more resilient, in any way. Men don't go on Oprah and cry about our hardships while she holds our hands, that's a woman thing. So, from a cultural standpoint, there's a certain unspoken degree of taboo about him turning to you for emotional support during his times of distress. And perhaps even a greater taboo about you trying to console him without being asked. But that doesn't mean your doing anything wrong by trying to cheer him up or help him.
Perhaps you could gently, gradually broach the issue of his shutting you out. Preferably at a time when he isn't already dealing with some other worry.
Let him know that you really want to have a close, trusting, intimate relationship with him. And let him know that part of forging that sacred bond is him inviting you so deeply into his life that his problems become your problems, your problems become his problems. Let him know that you carrying half of his burden for him is nowhere near as hard as watching him struggle under all that weight by himself. Let him know that hauling half of that weight for him is a price you are more then willing to pay for the happiness the two of you share. Let him know that sharing the inevitable downs of life are is an essential aspect of being a couple.
But don't push the issue too hard or too fast. Give him time to appreciate the logic of what you ask of him.
Something else you might want to consider, and perhaps this doesn't apply to him, but has he ever been exploited by anyone? Anyone whose ever had their weaknesses, their vulnerabilities exploited by somebody else will be deeply inclined to keep future vulnerabilities to themselves for fear of it happening again. That means any shortcomings, any failures, ect. Any tender issue an enemy could use to hurt them or manipulate them.
That doesn't mean that he won't open up to you because he doesn't trust you. It just means that on a very deep level, he is inclined to keep things to himself for protection. It's a reflex that runs so deep, it isn't easily overcome, even when dealing with someone he sincerely believes is trustworthy.
If this kind of situation is a factor in your relationship, it should gradually become more and more open to you over time. But perhaps, once again, a little gentle prodding on your part for him to take a leap of faith and trust you with these vulnerabilities might be worth considering.
Sorry for inundating you with so much waffle.

Hope at least some of it was helpful.
