Filing Taxes Self-Employed: Quarterly or Yearly?

By and large, being self-employed is great. Now that you’re the boss, you get to call the shots: you pick your projects, set your hours, and, when business is booming, you reap the rewards.

But every rose has its thorn. And for the self-employed, tax time can be pretty thorny.

When you plant your flag as a freelancer, contractor, or self-employed small business owner, the IRS sits up and takes notice.

When you worked for a wage, you hated those little lines of numbers at the bottom of your paycheck — why are they withholding so much? — but now that you’re responsible for keeping track of all your income tax liabilities (not to mention self-employment taxes), you actually miss the good old days of having taxes withheld by your boss.

Keep your head up! You left the rat race for a reason, and paying taxes as a solopreneur doesn’t need to be any more complicated than it was when you were working for a paycheck. Yes, paying taxes means paying attention, and saving all your receipts is a pain, but in just a few minutes (okay, maybe more like an hour) you can learn everything you need to know to keep the taxman off your back.

The first step? Finding out if you need to pay quarterly or annually. So let’s talk through the basics.

Understanding Self-Employment and Tax Obligations

Navigating the world of self-employment comes with its own set of tax responsibilities. If you earn income from freelancing, consulting, or running a small business, you’re considered self-employed (even if your “day job” is a normal employment scenario).

This means you need to be diligent about your tax obligations to avoid penalties and make the most of available deductions and credits. Self-employment income includes any earnings from your business activities, and you’ll need to file Form 1040 along with Schedule 1 and Schedule C when you submit your tax return. Understanding these requirements is crucial to staying compliant and optimizing your tax situation.

Quarterly estimated tax payments means four times the fun! (Well, maybe not)

From the official website of the IRS: “As a self-employed individual, generally you are required to file an annual return and pay estimated tax quarterly.” Individuals expecting to owe $1,000 or more are typically required to pay estimated taxes quarterly.

The IRS defines individuals as “self-employed” if they conduct business as a sole proprietor or independent contractor, if they are members of a business partnership, or if they earn direct income as a freelancer. As a solopreneur, you need to pay your good ol’ income taxes as well as self-employment (SE) tax, which represents your contribution to Social Security and Medicare.

As you probably know, the IRS loves rules and regulations. And just as they have rules for determining who is self-employed, they have another set of rules to help determine who needs to report and pay their taxes quarterly.

Bottom line: if you’re self-employed, you probably need to pay estimated tax four times a year. Some individuals may be exempt from the requirement to report and pay quarterly taxes (if your business generated a net loss of income, if you haven’t been in business for a full year, or if you have earned less than $600 from your business), but if you’ve been up and running for 12 months, and if you’re earning an income from your business, then it’s time to get to work on your quarterly estimated taxes. Failing to make these payments on time can result in an estimated tax penalty.

Estimates taxes are exactly what they sound like: using last year’s return and the worksheet found in Form 1040-ES, you pay approximately one-quarter of what you expect to owe the IRS at the end of the current year. If you overpay, then you’ll get a refund when you file your return in April, but if you underpay, then be prepared to fork out extra cash come spring.

And most importantly: Make sure that you pay your quarterly taxes promptly. If you report late, the IRS will penalize you at the end of the next quarter, and the penalties can add up quickly. Timely estimated payments can prevent unexpected tax bills.

Tax Facts To Keep in Mind When Preparing for Estimated Tax Payments

Like ordinary income taxes, your estimated tax payments will be impacted by a lot of different factors. Here are some things to keep in mind while you calculate how much you owe.

Business Structures and Tax Implications

Choosing the right business structure is a pivotal decision that can significantly impact your tax obligations, even as a self-employed taxpayer. The most common structures include sole proprietorships, partnerships, limited liability companies (LLCs), and corporations. Each comes with its own set of tax rules.

For instance, sole proprietorships are pass-through entities, meaning the business income is reported on your personal tax return. In contrast, corporations face double taxation — first on their profits and then on dividends paid to shareholders. Understanding these differences can help you select the structure that best aligns with your business goals and tax strategy.

Tax Deductions and Credits

One of the perks of being self-employed is the array of tax deductions and credits available to you. You can deduct various business expenses, such as the depreciation of assets, the business use of your home or office, travel expenses, and even meals and entertainment costs.

Additionally, the qualified business income deduction allows you to deduct up to 20% of your qualified business income, providing a significant tax break. Don’t forget about credits for research and development expenses, work opportunity tax credits, and disabled access credits. These deductions and credits can substantially reduce your tax liability, so it’s worth exploring all your options.

Record Keeping and Organization

Good record-keeping is the backbone of a smooth tax season for self-employed individuals. Keeping track of your business income, expenses, and deductions throughout the year is essential. This means holding onto receipts, invoices, and bank statements. It’s also wise to maintain a separate business checking account and credit card to keep personal and business expenses distinct. Consider using accounting software or hiring a bookkeeper to help with organization. These practices will not only keep you organized but also ensure you’re maximizing all available deductions and credits, making tax time a breeze.

Common Tax Mistakes to Avoid

Even seasoned self-employed individuals can make tax mistakes that lead to penalties. One frequent error is neglecting to make estimated tax payments throughout the year. If you expect to owe $1,000 or more in taxes, you’re required to make quarterly estimated tax payments.

Another common pitfall is failing to keep accurate records of business expenses, which can result in missed deductions and credits. Mixing personal and business expenses is also a big no-no, as it can complicate your tax situation and increase the risk of an audit. Staying vigilant about these common mistakes can save you time, money, and stress.

Filing Your Annual Business Taxes

As a self-employed individual you will still need to file an annual return and pay quarterly and annual taxes. Yes, this means another round of forms, but look at the bright side: if you’ve filed your quarterly payments accurately, this time you won’t owe them anything, and you might even get a little something back!

Disclaimer: The content on this page is for information purposes only and does not constitute legal, tax, or accounting advice. If you have specific questions about any of these topics, seek the counsel of a licensed professional.