21. Dating Coach: Up to $20,000 Per Month
The Internet is filled with men and women complaining about modern dating. Customs, expectations, best practices, and still people just can’t seem to figure each other out. As such, there is a high demand for dating coaches to help their confused fellow humans navigate the romantic landscape.
Because the job most often requires the coach to manage his or her own business, success varies across ventures. But when it works, it works. Sarah Jones, who graduated college in 2007 with plans to become an artist, now earns up to $20,000 a month teaching introverted men how to succeed with women.