Before you start
Decide if you want to do your taxes yourself
If the answer is no, stop reading this right now and call an accountant or a certified CPA. There's no shame in taking this approach. If numbers aren't your forte, hiring a professional will save you time and money, as well as your sanity.

"I recommend that everyone who freelances and has a day job get a really good accountant," says Stephanie Kuenn, who works for a nonprofit and moonlights as a freelance copy editor and proofreader of educational materials. However, if you think you can do your taxes on your own, you'll save yourself between $150 (for a return done by the least expensive accountants) and $1,000 (for an extensive return prepared by a CPA). "It's a confidence issue," says Howard Samuels, a CPA at S & C LLP in New York. "If [freelancers] know the stuff pretty well, there's no reason they are going to need me." (Remember that the money you pay an accountant is deductible, so you'll get some of it back.)

Invest in tax prep software
If you choose to take on the mass of complicated forms that make up a tax return, you are a brave soul, but you're not alone. Head to your local office supply store and purchase a copy of TurboTax. It's not the only tax software on the market, but it comes highly recommended. "In today's world, unless you have an incredibly simple return, it's definitely worth buying," Paul Silver, a partner at Hinckley, Allen & Snyder LLP in Providence, Rhode Island, says. "For a person who's not afraid of numbers, TurboTax is going to be fine. There's no reason to spend $400-$1,000 [on an accountant or CPA] when you can spend $60." The best part? The price of the software is tax-deductible.

Decipher the extra taxes freelancers must pay
While being self-employed has its benefits, it also carries some negative tax implications. When you work at a company, your employer pays half your social security tax (7.65 percent), but those who are self-employed are on the hook for all 15.3 percent. The government does throw you a bone, however, as Samuels says you can deduct half the "Self-employed Social Security Tax" on page one of your tax return as an "adjustment to income.

Also, be aware that certain cities and states also have unique regulations regarding freelancers. For example, in New York city, if you net more than $55,000 of freelance income and have not incorporated, Samuels says you are subject to a roughly 4 percent "Unincorporated Business Tax."

Know your Schedules
On your return, your W-2 wages will be recorded on line 7, while 1099s will go on Schedule C. For freelancers, the difference between these is vital. Schedule C is comprised of your freelance wages (income where tax has not been taken out) minus your business expenses. The restrictions on Schedule C deductions are fewer, a fact we'll get to next.

While preparing your return
Understand all you can deduct
While there are serious restrictions about itemized deductions, almost all business expenses can be deducted against Schedule C income. "Self-employed people have an advantage because there are fewer restrictions," Silver says. All those pens you bought? Deductible. The cab ride to meet a client? A write-off. The lunch meeting with said client? Also a business expense, but only 50 percent of it. (Assuming you have to eat, the government only gives you half credit.)

If you have enough expenses, your Schedule C income will be negative. This often occurs in your first year or two, for example, if you are waiting tables while freelancing on the side. Your net income, upon which you pay taxes, will be less than what you made waiting tables because you will add the negative Schedule C income to your wage income. Be aware, however, that if your Schedule C income is negative year after year, the IRS will possibly start asking questions about why you continue to run a business that loses money.

Uncover commonly missed deductions
Since she recently started contributing to the "Showtracker" TV column for The L.A. Times, freelancer and former mediabistro.com contributor Claire Zulkey writes off her cable TV bill. Moral of the story: Think creatively about possible deductions, but be honest. According to Samuels, other frequently missed deductions include a home office (you can deduct a percentage of your rent, based on the square footage of your house or apartment you use as an office), not deducting self-employed health insurance, and not deducting "fixed assets," such as a computer or furniture. Silver says that by electing to take a Section 179 expense deduction, self-employed people can deduct the entire cost of these items at once, instead of depreciating them over a set number of years as defined by the IRS. (For example, a computer is depreciated over three years.)

Silver says that whenever possible, take the whole deduction, unless you plan to make significantly more money the next year (and enter a higher tax bracket). Don't be dissuaded by the detail work, as every little bit reduces the amount you have to fork over to Uncle Sam. (One common mistake: The home office deduction cannot make your Schedule C total negative. If you made $5,000 and have $4,000 in expenses plus a $2,000 home office deduction, you can only take $1,000 of that. You should still record the other $1,000 deduction for your own purposes, however, as it can be rolled over to the next year.)

Figure how much to deduct
Filling out your tax return is not an exact science. Many deductions are based upon the percentage of the time you use something for business. In a case like Zulkey's cable bill, Samuels says "It's a gray area. For TV people, if they want to be conservative, we use 50 percent of the bill." Your business calls are deductible, but if you make personal calls on the same phone, you can't legally deduct the entire bill. There are two options: Either get a record of your calls from the phone company, figure out which ones are business-related and deduct that percentage of your bill, or estimate. Likewise, if you take a six-day trip and work for three of the days, you should deduct half of the plane fare, hotel and other expenses incurred. Then again, you could go Conrad Black on the whole affair, deduct the full amount and pray you don't get a letter from the IRS asking you to explain how that week long jaunt to Cabo was entirely business-related.

Know where to turn for answers
Whether you've never done your own taxes before, or April 15th is your favorite day, you're going to have questions, and it'll help to have people in the know to answer them. Last year, Zulkey found herself owing $8,000, and asked her freelance friends for help. More experienced freelancers are an excellent resource. If you don't have friends in this situation, search in other places, such as the mediabistro.com discussion boards. Kuenn suggests that writers "look for someone who specializes in [doing taxes for the self-employed]." She and her friends all go to one woman, a part-time artist who works as an accountant to pay the bills. Samuels says that he knows little about hedge funds, but is a great resource for the self-employed. If you have to, call an accountant, as the piece of mind is worth the price.

After you've filed
If the IRS questions your return, write the taxman back
Worst-case scenario, you do get a letter from the IRS. Don't panic, just reply. Both Silver and Samuels say that the majority of these letters are mistakes by the government: An irregularity on your return triggered the system to send a letter to you. This does not necessarily mean you are in trouble, but it does mean you need to explain the situation. "If you're not cheating, you have nothing to fear," Samuels says.

Your worst move is to put the letter in a drawer and forget about it, because the IRS will get their money one way or the other. "I had a client come home to a padlock on their door," Samuels says. "He called me and I asked him whether he got any letters [from the IRS]. He said, 'Yes, but I just threw them away.' If you ignore them, they will win."

Prepare for next year
Like they say, life's two certainties are death and taxes. Next April 15th is only 13 months away, and there's no reason you can't start preparing now. If you haven't already, start a filing system where you keep receipts for business expenses, noting the date and type of expense. It doesn't have to be fancy -- a simple folder will do, since you can separate everything later -- but having everything in one place makes tax tabulation easier. Most importantly, stay on top of your financial situation.

Noah Davis is assistant editor at mediabistro.com