I've found that one way you can help people to see the assumptions they're making that may be limiting them in life is to simply listen and reflect back what they've told you. For instance, you might say to your friend, in the example you're talking about, "so you're worried that when you have a job, you won't be able to hang out with your friends as much."
Hearing our own beliefs about how the world works reflected back to us helps us to evaluate those beliefs objectively and determine (1) whether they're true and (2) whether they're serving us. When we do this for others, it helps them feel heard and understood as well.
Best,
Chris
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