I am a freelance writer and one of my regular clients will not answer my questions about taxes. He pays me in checks, and while it seems on the up-and-up, I know I’m making enough from his company to report it (I made around $2,000 from him in 2014 and expect to make around $7,000 this year). With someone else, I might simply stop working for them, but we’ve known each other for years. I like him as a person, and respect him in many ways. I don’t want to offend him and I also don’t want to lose him as a client.
John: I spent, like, four hours one night last week entering tiny numbers into TurboTax, then was crestfallen at the result, and did the same with H&R Block online. Now both of them are emailing me like, HELLO? DO YOUR TAXES AND PAY US… so I’m putting it off. For now. I did actually go to see a human person at an H&R Block office, and she told me it would be $300 just to process my 1099-MISC, nevermind the taxes I will inevitably owe, so I scuttled back to my desk.