<prompt> Human: Hey All! This is my 3rd year freelancing and 1st year filing taxes as an independent contractor. I work a an audiovideolighting technician with several side gigs in design and fabrication. I was a salaried desk jockey for about 10 years previous to that so Im still relatively new to the IC game. Ive put aside about 2k for the purpose of paying the money Im going to owe. This was my best year so far-55-60K-, which is starting to look a lot like a double edged sword due to all the w9s I had to filled out this year. Ive gotten a wide variety of tax advice from friends and colleagues, but I wanted to tap the collective for some thoughts on how to handle this years taxes and better prepare for next years avoidance of the Pain monster. EDIT: I have read my post several times and realize it is awful. Ugh. Thank you for all of your responses, negative and positive. I did not include anywhere near enough information. About 65 of my income is thru subcontracting for various event companies this year. I have chosen to be W-4d at any company that had the option. I started freelancing soon after I quit my desk job, so that year my taxes floated in between the 2. I made VERY little as a freelancer that year. The next year I worked completely under the table so my reported income was negligible. This was my first year really making money on the books as a freelancer. I understand Im going to get dinged pretty bad. I was looking for some ways that some of the other freelancers here have dealt with these things. Thanks for your time and consideration.  <response>: Have you been making your quarterly payments of estimated tax? I sure hope so, if 2K is all youve set aside. Youre on the hook for both the employer and employee portions of SSMedicare taxes 15.3 flat on your adjusted income, income taxes, and a penalty for underpayment if you have not been submitting quarterly payments. 