I don’t think wanting to work in the creative arts means you are entitled. The Tories peddle this nonsense. They ran a campaign saying ballet dancers should work in tech. What you and they are really saying is only posh people who can afford it should take a chance and work in the arts as a freelancer.
I agree, but the point is that Jack has made enough money to live on over the years. Yes, she's probably burned through a lot of it, spending it on designer stuff, but that's her problem, not anyone elses. Her latest grift isn't 'I'm not making enough money to live', it's 'please keep me in the style I'm accustomed to', which is where the entitlement comes in. Not so long ago (maybe a couple of months, if that) she was tweeting about how if she saved enough deposit she was looking to buy a house or flat in the region of £500,000. Now apparently she can't afford to buy shampoo and conditioner? This isn't someone on the bones of her arse.
I applaud anyone who gives their chosen career a go, especially if it means them being short of money for a time. But if, like Jack claims, you haven't made it or it isn't paying you a fair wage after ten years, the sad truth is a) you probably weren't good enough in the first place and b) you need to start looking at doing something else or at least something that will supplement you along side it. And that's without going into the whole thing of whether Jack is a posh person or working class (I'll give you a clue here. She's definitely not working class. She's grammar educated, her grandad was a landlord who left an estate of £1.3 million, and her dad has an MBE and had a high up job in the fire service).