Starting Out Salary: -$100

You've finally got yourself a blog and have started answering emails for your advice column on relationships. Sadly, nobody likes your spin on answering everything with Scientology references, or advising everyone to find their inner alien.

Local Newspaper Gig, Salary: $20,000

You're writing a "letters to the lovelorn" advice column at the local paper in your small town. You're buoyed by the circulation jump when your column takes off, as you tell a guy to leave his self-absorbed, workaholic, arrogant, know-it-all girlfriend. Sadly, that guy was your boyfriend. Oh well, the life of a writer is a lonely one.

Your Blog's a Hit, Salary: $30,000

You love your job and love writing from home. To you, every day at work is Pajama Day. You dish out smart, sassy advice and your audience seems to be responding. You get about fifty emails a week asking for your advice, which seems plenty for now. You've finally got a monthly hit count on your advice blog of 100,000 readers and make $6 CPM per month. Maybe next year you'll be able to dig yourself out of bankruptcy and afford more than ramen noodles and mac 'n cheese boxes for dinner.

Magazine Advice Columnist, Salary: $60,000

You land a column in a hot, hip women's magazine. You may get tired of all the questions about how to make a boyfriend treat you better or get frustrated at all the whining about spouses, but it's a job, and a well-paying one at that.

Ask You Anything, Salary $250,000+

Your advice column "Dear Star" is nationally syndicated in eight states and has been translated into five languages. You've written six best sellers on relationships, and you have your own TV program and a radio talk show. Your latest best seller is a compilation of your most popular columns from the past fifteen years; it is being turned into a hit movie starring Jennifer Lawrence as you.