How far to push them out of their comfort zone (and how hard to push)?

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<p>I agree with this advice. If you are comfortable with the money issues, help him get comfortable with moving out into the big world. A lot of that can come from saying, “I’ll always care about you and be proud of you wherever you go,” while making clear that you think he should explore all possibilities before making up HIS mind. </p>

<p>Congratulations on the great set of choices.</p>