I am always torn when I read something like this. On one hand, I want people to be able to pursue their passions. On the other hand, I know that it is impossible for the world to function if everyone got to only do what they want.
This person wants to be able to earn a living doing whatever they want, but they also want to enjoy the benefits of other people doing things they don’t want to do. They want to be able to travel, but that requires other people to do a lot of labor they probably don’t want to do. The boarding agent, flight attendant, and pilots likely all don’t want to be doing what they are doing while he flies. The person who cleans the plane and loads the luggage aren’t doing what they want to be doing.
This is going to apply for so much of what the author is going to expect from others to support his lifestyle of doing whatever he wants whenever he wants. He wants to write while other people grow his food, provide his infrastructure, the services he requires.
In the end, I don’t think it is a healthy goal for people to expect to not have to do work that they don’t want to do. Sure, it might turn out that you can support yourself doing what you wanted to do anyway (although even then you will probably have to do a lot of stuff that isn’t what you want to do, too), but I don’t think you should expect it or define success in life as being able to do that.