The barriers are coming down. Thanks to the internet, you can be a taxi driver(uber), a hotel room(airbnb), retailer(ebay/craigs), commercial artist (etsy, cdbaby, youtube) and more – all at once!
Legitimacy is no longer achieved via licensing, permits, or getting picked by a record company.
You can pick yourself, and go about developing an audience of customers and fans who vouch for your reputation. You can align with apps and websites to fulfill many of your tasks and responsibilities.
Technology’s empowerment of the individual makes it cheaper to be a company, and it is reducing the demand for services from companies that provide 40-hour week jobs. Companies entrenched in doing business the way it was before the internet are having a tough time adjusting. (Taxi companies, record companies, etc.)
Technology also makes it cheaper to live – air travel, lodging, meals, etc… the internet brings the world to you at a discount.
For creative people who can adjust their lifestyle (expenses) so they no longer feel they need a 40-hour job with “security,” there is a lot of opportunity to create a remarkable and interesting life.