Just my opinion:
The first implies expectation (i.e.; that's normal and expected). It could be a slightly Narcissistic response. As if he is saying, "I've been the bread-winner and your extra income would be appreciated" - it centers the conversation around him.
The second would imply that he is proud of you, and you are taking steps to advance yourself and become financially independent.
Edit to add: my mom is Narcissistic. Impossible to please.
Edit to add 2: I'm sorry if I inadvertently killed your thread. It happens quite a bit 
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Aspie score: 161 of 200
Neurotypical (non-autistic) score: 38 of 200
Autistic/BAP -123 aloof, 124 rigid and 108 pragmatic
Autism Spectrum quotient: 41, Empathy Quotient: 19