The Best Way to Go Broke

W h e n . C o f f e e . S p e a k s .

How many trees can you plant before you're in the red? How many trees can you plant before you’re in the red?

Yesterday I checked a big ticket item off my “being a freelancer in 2014” to do list: I got Obamacare. For better or for worse, for richer or for poorer, I can now count myself among the Ranks of the Insured. After suffering through several terrible customer service representatives, I finally got someone useful on the phone. While reviewing my application he asked me to verify my annual income for the past year, and I confirmed the embarrassingly low total that I’d listed. The rep asked me if I expected the same income in 2014, and I told him that I hoped not, explaining I’d spent the past year completing a project that I knew from the outset wouldn’t make me any money. He sheepishly inquired, “Do you mind if I ask what it was?” I told him I’d…

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