Help! My boyfriend won’t pay his taxes. It’s been six years since he had a full-time job, and ever since he went freelance in 2010, he has not been able to complete his 1099s.
There are a few reasons for this. For one thing, he feels somehow that he’s getting cheated, because his quite sizable reimbursements required for his job have been lumped in with income. (I’ve explained to him that he just needs to write off these expenses, but he won’t listen.) Also, he struggled with a pretty heavy alcohol addiction that, thankfully, he finally took care of about six months ago. And now he owes so much (over $10,000!) that he’s just overwhelmed by the whole thing and can’t bear to face it. I’ve tried pleading with him, nagging him, offering to do his taxes myself, etc., and also tried pleading/nagging/yelling to get him to see a psychotherapist, to no avail. (He quit drinking all on his own, miraculously.)
We don’t have any shared accounts, so I’m not personally responsible in any way, but I’m just so fearful about what bad things might happen if he doesn’t take care of this problem that I don’t know what to do. —Fearing the IRS
Taxes force us to confront our relationship to money. No wonder they’re overwhelming! Our feelings about money can stem from our upbringing; perhaps your boyfriend’s parents were stingy, or else obsessive about household budgeting in ways that felt controlling.
If we’re political, taxes may also ignite our rage at the state, especially the American system. I stare at my pile of 1099s and wonder: Why are my tax dollars funding war and destruction? How about decent schools, clean energy, and ending hunger?
Also, freelancers’ taxes are a pain in the ass. Not only must we track our expenses, but the system feels rigged against us: In New York, for example, the self-employment tax is brutally regressive. Freelancers in Germany and Holland tell me that, in those countries, the process of paying taxes is no better for self-employed workers, perhaps even more onerous. But like other middle-class people in Europe, they find their tax dollars returned to them in the form of universal public services. This eases the pain of paying. Julie Phillips, an American freelance writer who lives in Amsterdam and is married to a Dutch freelancer, explains: “You get a lot back [for your taxes] here. Good schools. Affordable university. Democratic socialism works.”