I think the connotation is that they feel as though they ought to be able to obtain a livable job doing what they want to do, which is not the case. They aren't necessarily entitled, but are naive and have unrealistic expectations.
Just because one loves writing does not mean that they will be able to secure employment as a writer. Yet, students continue to enter writing programs and graduate with useless degrees, expecting to enter the workforce immediately. Certain positions simply aren't in demand, yet students act as though finding employment will be trivial.
I also believe the world has tended to conflate talent discovery with the talent quantity, because historically, talent discovery was up to a select few gatekeepers (like record labels and publishers), who could (or would) only showcase a small fraction of the available talent pool. Whether they did this because of unavoidable resource constraints or to ensure an artificial scarcity is another debate.
Now that anyone with a decent amount of talent and/or the willpower to put in some effort into honing a skill can also showcase that skill, the supply of writers and singers and musicians has suddenly become much larger than before. So it follows that the price associated with purchasing access to the fruits of these talent/labours will have dropped.
Just because one loves writing does not mean that they will be able to secure employment as a writer. Yet, students continue to enter writing programs and graduate with useless degrees, expecting to enter the workforce immediately. Certain positions simply aren't in demand, yet students act as though finding employment will be trivial.