Taxes....A Cautionary Tale

At some point in our lives, most people will work for cash and get paid 'under the table'. The young are especially drawn to this kind of work, where you walk away with a fist full of bills and no real commitment needs to be made. It now shames me to say that 2 years ago I was drawn into this type of working relationship and have just now finished dealing with the consequences.

In my defense, the allure of this job was not the easy cash. I was working as a financial analyst for the government at the time and was desperately trying to find another job in the PR/Marketing/Advertising field like every other 20 Something in America. I responded to an ad for a 'Freelance Social Media Account Manager' (whatever that meant) and was thrilled to get an interview.

I met with the owner of this small, local marketing firm (which is now, shockingly, out of business) at a diner for a lunch interview. I loved his business model, his easygoing nature and of course, that he seemed to really like me. He hired me on the spot. Over the next year and a half, I updated clients' Facebook and Twitter accounts and was sent a personal check for $400 every 2 weeks.

During this time, he constantly told me that I was by far the most dedicated of all of his 'staff' (which consisted of 4 or 5 other naive 20 Somethings) and that once the business got a little bigger he would take me on full time. Desperate as I was to get out of my cubicle, I fell for it hook, line and sinker.

As I said before, he paid me in cash. When the first tax period came around, I didn't even think about it and did not claim the couple of months I had worked for him. It was the second tax period that just about ruined my life. He claimed me as an 'independent contractor' and, long story short, I ended up owing the IRS about $2,000.

And I ended up paying some idiot at H&R Block $300 to tell me I owed $2,000.

Between January and April I worked my ass off trying to get the money together but, come April 14th, I was still short. I paid $1,200 and got an extension for the rest. About 1,000 hours at the restaurant later, I paid off the rest and I feel like a boulder has been lifted off my shoulders. Learn from me, all you 20 Somethings out there. Save yourself months and months of stress and hours on your feet pretending to be nice to people for tips. No good will come from trying to cheat the tax man.