Quarterly tax estimates, which include both income and self-employment taxes, fall due on April 15, June 15, September 15, and January 15. The first one covers income earned between January 1 and March 31, the second one relates to April 1 through May 31, the third one attaches to June 1 through August 31, and the final one handles income from September 1 to December 31.
Problems arise when income varies, and likewise the quarterly payment varies. A form 2210 must be attached allocating income and tax payment by period to prevent assessment of a penalty. The IRS automatically assumes a steady income stream unless otherwise shown.
For those who work and freelance, a loophole exists for catch up. Income taxes withheld by an employee are considered equally paid throughout the year no matter the actual date of withholding. Some employees increase their withholding in November and December if they anticipate a tax liability.
IMO, anyone making five figures from freelancing should probably engage a professional accountant. Those who reside in college towns can probably find a tax professor who prepares tax returns on the side and get a 25 to 50 percent discount.
The obvious deductions for freelancers are easy. Mileage to and from an event, cell phone, internet service, computer equipment and supplies, subscriptions, professional dues. The easier thing to do is log the trips and keep the receipts in a file then summarize them at year end.
The home office issue is very tricky. I recommend professional advice before taking that plunge. Most CPAs discourage it because of the audit frequency and the inflexibility of the IRS regulations.
