NEW YORK (MainStreet) – The premise of this piece started out simply enough: Is it easier for a taxpaying freelancer to pay quarterly or to take a penalty and make one lump-sum payment by April 15?

Like freelancing itself, however, it became far more complicated than it seemed on the surface. The result read like a point-by-point rebuttal of everything the author of this story did incorrectly after becoming a freelancer in 2008. The financial advisors, financial planners, certified public accountants and tax-preparation professionals not only spelled out the level of preparation and dedication it takes for a freelancer to sort out their finances before tax season, but the implications of some of the worst missteps a freelancer can make.

“Most people who become freelancers have neither the experience nor the desire to see themselves as a businessperson, and that's what every freelancer is,” says Susan Lee, an enrolled agent and certified financial planner who specializes in tax preparation for freelancers. “Everybody wants their own chief financial officer to come take care of their finances, they want a chief business officer to come take care of their vacations. Whatever they want, they don't want to spend the time and the energy to learn how to do it and just do it.”

As Lee and her colleagues collectively pointed out, the self-employed are not only required to file an annual return, but also pay estimated income taxes quarterly to avoid penalties (welcome to Form 1040-ES). You have to pay either 90% or more of the tax for the current year or 100% of the tax shown on the previous year’s return to avoid being hit with a penalty. If you're a freelancer, independent contractor or business owner successful/unfortunate enough to make an adjusted gross income over $150,000, you'll have to pay 110% of that year's levy. Once you've figure out that amount, you can mail your quarterly payments with Form 1040-ES vouchers or pay electronically.

“Though calculating your income each quarter may seem like a hassle, it provides you an opportunity to regularly review your business profitability, which is an added benefit,” says Melinda Kibler, a certified financial planner for Palisades Hudson Financial Group in Fort Lauderdale, Fla.

There are freelancers who don't take this route for various reasons, though — including the fact that having a bunch of that cash on hand isn't such a bad thing during emergencies or during a particularly imposing tax season. As Lee points out, a failure-to-file penalty can be as little as 5% a month before topping out at 25% of unpaid taxes. Meanwhile, the punishment for failure to pay those taxes starts at half of 1% before hitting as much as 25% of the unpaid levy. Jonathan Medows, a certified public accountant who tailors his service specifically to freelancers, notes that some of his more cash-sensitive clients prefer to absorb the penalties and lump-sum tax hit, especially if much of their revenue and spending comes at the end of the year.

”Clients geared toward the end of the year will just pay the penalty because it's cheaper than applying for a loan,” Medows says. “You have this money, you don't know what's coming in the door, and parting with a lot of cash is very uncomfortable for a lot of them.”

For most other taxpaying freelancers, that's a scenario they'll want to avoid. As Kibler from Palisades Hudson points out, even estimated tax payments are just part of what a self-employed person has to worry about during tax season. The self-employment tax — the Social Security and Medicare tax typically withheld by employers for employees — now falls into their laps as well.

That's no small deal. Let's say an employee in 2015 and his or her employer pay 6.2% Social Security tax and 1.45% Medicare tax apiece on that employee's $118,500 in earnings. If that worker is self-employed, he or she is suddenly responsible for 12.4% of Social Security tax and 2.9% of medicare tax on that $118,500. If he or she is part of a couple who declares $200,000, or $250,000 while filing jointly, they may have to pay an additional Medicare tax of 0.9% for any amount above the threshold.

“You've got to be hyper-organized and vigilant about everything,” Medows says. “If you're working for yourself, there's more of an onus to do it, because nobody's going to do it for you. There's no HR department, there's no accounting department, you're it.”

As Lee notes, that means keeping track of every check that comes in to make sure 1099 forms include both earnings and repaid expenses. It means keeping track of payments too small to warrant a 1099. It means keeping hard copies of all your receipts — even if it means you just put them into a folder as soon as you get them — and breaking them down into categories before tax time. It means realizing that, no, checks and credit card statements aren't substitutes for receipts, as the former are statements of purchase, not of payment. In general, it means getting organized to a far greater degree than your W-2 holding counterparts.

“As a self-employed individual, taxes can be more complicated,” Kibler says. “It is of the utmost importance that you keep thorough records and revisit your tax liabilities quarterly, in order to ensure you avoid penalties and remain in good standing with the IRS.”

Sometimes, that requires help. A freelancer can set a rule of thumb like putting away a third of his or her earnings to pay taxes, but that's often an overly optimistic goal. Ideally, a freelancer should get in touch with a financial advisor, a certified public accountant, a financial planner or even their tax preparation professional long before it's time to settle up the tab for the year.

“What I would recommend to the small-business owner is to sit down with your CPA midway through the year to get a sense of where things are at, if you're performing as expected or if there's something unexpected lurking in the shadows,” says Roman Kozak, vice president and senior retirement planning consultant at RBC Wealth Management. “You can prepare your CPA for the potential that you may be earning more than you expected or that you may have some opportunities to take losses.”

At the very least, Medows says, a freelancer will want to meet with a professional just to iron out the basics: structuring a business to minimize the following year's tax burden, helping pay estimated taxes, building an accounting system for revenue and spending and making sure you have financial resources for taxes and other concerns.

Cost does become an issue, but all of the financial professionals we spoke to emphasized that tax software doesn't guarantee a decent return and that even the most polished professionals at a tax preparation chain can't help you if the office isn't open. Much as the self-employed need to occasionally check up on current affairs to see if the national or global economy is putting them into a position in which theirs is the first job cut, they should really check in with a professional to avoid similarly nasty surprises in their tax return.

“Translated from Yiddish: 'Man plans and God laughs,' meaning you can plan all you want, but what happens if you hit a recession?” Medows says. “Sometimes it's not you, it's the economy. Sometimes you have to pay attention to macroeconomic forces beyond your own little world.”

— Written by Jason Notte for MainStreet

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This article is commentary by an independent contributor. At the time of publication, the author held TK positions in the stocks mentioned.