If you'll think about it, there is actually a huge difference.
The comment I replied to was talking about how as (mostly) programmers, we have a skewed perspective on the job market. Most people in our age range don't get the kinds of job offers we do, and are badly underemployed.
She took a job she was overqualified for anyway, because there was nothing else available, and hates it. He decided to mooch off his parents because he was entitled to a management job (he makes a small amount of money, but spends it all on entertainment).
Being underemployed, and realizing it, is not a sense of entitlement. Asking for handouts because you can't get the job you want (when others are available) is.
Why not? Is it the kind of writing that she'd be doing (many secretaries write a lot) or is it that she doesn't want to be a subordinate?
I'm beginning to think that the difference between them is that you think that she's entitled to what she wants and he isn't.
After all, one could say that he just doesn't want to use his management degrees to be an individual contributor.