I firmly believe the ability to "make it" in the world is one that is ingrained in children at a young age- or not. Whether he has a job or what his ambitions are are just details, and his ability to deal with things comes from the things you taught him from the moment his slimy little ass came into the world. I know some of the obstacles you have had to overcome in the past few years I've known you, and I imagine you've taught him (intentionally or not!) that as long as a man stands on his own two feet and keeps moving forward he'll never fail. He may fall, but as long as he keeps getting up and taking another step, he should be ok.
I'm not a parent, but I've always thought that the advice Polonius gave Laertes in Hamlet Act I Scene 3 makes more sense than anything else I've ever heard.
And these few precepts in thy memory
See thou character. Give thy thoughts no tongue,
Nor any unproportioned thought his act.
Be thou familiar, but by no means vulgar.
Those friends thou hast, and their adoption tried,
Grapple them to thy soul with hoops of steel;
But do not dull thy palm with entertainment
Of each new-hatch'd, unfledged comrade. Beware
Of entrance to a quarrel, but being in,
Bear't that the opposed may beware of thee.
Give every man thy ear, but few thy voice;
Take each man's censure, but reserve thy judgment.
Costly thy habit as thy purse can buy,
But not express'd in fancy; rich, not gaudy;
For the apparel oft proclaims the man,
And they in France of the best rank and station
Are of a most select and generous chief in that.
Neither a borrower nor a lender be;
For loan oft loses both itself and friend,
And borrowing dulls the edge of husbandry.
This above all: to thine ownself be true,
And it must follow, as the night the day,
Thou canst not then be false to any man.
Farewell: my blessing season this in thee!
My guess is he'll be fine. You've taught him well, and he has a trusty SAK, and that's pretty well the best you can do.
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