Too Many Business Owners Overpay on Their Taxes. Are You One of Them?

Here are some common reasons you may be overpaying on your taxes — and what you can do about it. 

When you work for yourself, it’s easy to focus on the daily hustle — and put off dealing with what you owe the government until tax time. 

What most solo business operators don’t realize: the U.S. tax system is actually stacked against them. The IRS gives some advantages to corporations and W-2 employees that solopreneurs don’t get. If you’re self-employed, you’re set up to pay more taxes by default. In fact, the typical freelancer making over $200,000 overpays by a staggering $15,000 each year!

But there’s something you can do about it. We’ll walk you through some of the common reasons self-employed workers overpay their federal taxes and how you can take advantage of the system, so it doesn’t take advantage of you. 

Understanding Tax Overpayment

Am I paying too much in taxes? 

Why do I pay so much in taxes?

Lettuce gets these questions all the time. And the answer to both is simple. If you’re a solopreneur, the U.S. government has created a system that’s more favorable to corporations than it is to you. The result: you’ll wind up overpaying on your taxes unless you take active steps to use the system to protect your hard-earned money.

Here’s the breakdown. In America, everyone who works pays Social Security and Medicare taxes, which add up to 15.3% of annual earnings. If you’re a W2 employee, tax law requires your employer to pay half of those taxes. That’s part of the federal withholding that comes out of your paycheck when you fill out a W-4 form. 

When you’re self-employed, the federal government requires you to pay both the employee and the employer share of your Medicare and Social Security taxes. This is commonly referred to as Self Employment Tax. That means freelancers, independent contractors and solo business owners are on the hook to pay double what W-2 employees pay on those taxes. That can translate to thousands of dollars, if not more, depending on your income. 

Curious if you might be overpaying?

Try the Lettuce Tax Calculator to see how much more you can take home each year.

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Common Scenarios That Lead to Tax Overpayment

In addition to the built-in disadvantages of the American tax system for solo business owners, many self-employed people overpay on their taxes for other reasons. Here are some common ones: 

Lack of tax knowledge

The main reason freelancers and solopreneurs overpay their taxes is simply because they don’t have an adequate understanding of current tax laws, both on the federal and state level, which can be confusing and complex. Many of the established tax rules designed to help solo businesses aren’t widely known, and were previously too complex and tedious to maintain. 

Underpayment penalties

Most self-employed people are required to pay estimated income taxes every quarter. If they don’t, the IRS can force them to pay a penalty. Because of rising interest rates, the IRS raised its penalty for individuals to 8% per year as of late 2023, up from 5% in 2021. 

Incorrect filing

Filing errors can lead to unintended consequences, with an impact not just on your tax payments but in potential missed tax credits and liabilities, amended returns, costly adjustments, and accuracy-related penalties. Errors and inaccuracies can also trigger dreaded tax audits or result in legal issues. 

Outdated tax preparation methods

When you use outdated tax preparation methods that rely on paperwork and manual calculations, you increase your risk of filing errors. As the tax system increases in complexity, the tools we use to keep an edge must increase in capabilities. Without the latest tools and knowledge, you’re also far more likely to miss out on new deductions and credits — and potentially run afoul of constantly changing tax laws. 

Overestimating income

If you’re self-employed and receive a tax refund after filing, it’s because you overestimated your income or miscalculated your estimated taxes. Instead of putting that money to work for your business in the form of investments or cash flow, you’ve effectively given the government an interest-free loan. Overpayment may seem harmless, but it can also lead to: 

• Lower deductions: Some deductions and credits are phased out at higher income levels. Overestimating your income can lead you to mistakenly conclude you’re ineligible for certain tax benefits, resulting in a higher tax bill.
• Adjustment headaches: Readjusting your estimated tax payments or withholding mid-year can be complex and time consuming.

Missed deductions 

Taking advantage of deductions can significantly reduce your taxes. But there are many common deductions that solo business owners often miss, including: 

• Home office expenses: If you use part of your home exclusively for business, you can deduct a portion of your rent or mortgage, utilities, and maintenance costs. The standard deduction lets you write off $1500 for your home office ($5 per square foot of office for a maximum of 300 square feet). Savvy business owners end up with a plan that’s customized to give them two to three times more savings. 
• Business mileage: Keep track of your business-related travel to deduct mileage.
• Office supplies and equipment: Items like computers, printers, and office furniture can also be deductible if you bought them for work.
• Professional fees: You can deduct costs for legal, accounting, and other services if they’re work related.
• Advertising and marketing: Expenses for promoting your business, including online ads, and business cards can also offset your taxable income.
• Travel expenses: You can write-off costs for business travel, including airfare, lodging, and meals. 
• Education and training: The cost of courses and materials that improve any skills related to your business can be deductible as well.
• Retirement: Solo entrepreneurs often miss out on several retirement deductions that can significantly impact their savings. Among them: your 401k. If you have an S-Corp — a type of business that can save solopreneurs a lot of money — you can contribute as both an employer and an employee, allowing you to save more for retirement and benefit from almost twice the tax deductions as you can as an LLC or sole proprietor.

• Healthcare: If you're a solopreneur with a health insurance plan for your business, and you’re not eligible for an employer-sponsored plan (including from your spouse) you can deduct the health insurance premiums that you pay for you and your dependents from your taxable income. 

How to Reduce or Avoid Tax Overpayment

When you’re a solopreneur, you answer to no one but yourself (give or take the occasional high-maintenance client). But as the master of your own enterprise, you also take on all the responsibility and risk that comes with being your own employer. 

Just ask Lisa Dini, a former marketing consultant who now leads community and public relations for Lettuce. “After two years of consulting, my accounting function consisted of an invoice tracker, a receipt folder in my email, and prayers that I put enough away in savings to cover the tax bill,” she says. Then she got proactive in how she dealt with the IRS.  

Here a few important ways to do so:

Stay informed

Staying up-to-date on tax laws and regulations is key. As a solo business owner, the more you understand about the evolving tax rules that directly affect you, the greater your chances are of avoiding tax overpayment and getting the most tax savings possible. 

Keep accurate records 

Though it’s often an afterthought for freelancers, maintaining accurate financial records can have a big impact on your business. Separate your company’s finances from your personal ones, and use a dedicated business bank account and credit card for all work-related transactions. Keep digital copies of your receipts and invoices, and maintain organized records of every financial transaction. 

Embrace tax technology

Tax software and AI bookkeeping software can help make sure you don't overpay your taxes. These tools can perform complex math accurately and frequently, check your filings for errors, calculate and pay estimated quarterly taxes proactively, and prevent underpayment penalties. The tools can also help you identify all the eligible deductions and credits you may qualify for. 

As Dini puts it: “Having one solution that automates all my bookkeeping and accounting gives me a new sense of confidence and saves me so much time.”

Get professional advice

When in doubt, consult a tax professional or an AI-based tax professional service. Depending on your situation, there may be nuances in the law regarding everything from self-employment taxes to tax credits that require more expertise. 

Traditional or AI tax and accounting services can come at a steep cost, but advances in technology have opened up an affordable middle ground.  

The Magic of Switching to an S-Corp 

By default, the U.S. tax system treats a solopreneur as both employer and employee, requiring you to pay more taxes. But there’s a way to make the system work to your advantage: become an S-corporation. 

S-Corps are designed for businesses of one, and they’re perhaps the best-kept secret of tax accounting for savvy solopreneurs. When you designate your solo business as an S-Corp, you're able to split your income into two parts: "salary" and "owner's distribution." You only pay payroll taxes on the salary portion, not on the profit you take home as an owner. 

In addition to lowering your taxable income and federal income tax liabilities, setting yourself up as an S-Corp allows you to benefit from the tax advantages typically reserved for larger businesses. As an S-Corp, profits and losses pass through to your personal tax return, reducing the self-employment tax your solo business pays. You gain access to corporate-level benefits, with more options for healthcare and retirement savings, along with increased eligibility for tax deductions and credits. Establishing yourself as an S-Corp can also boost your business's credibility with clients, customers, and suppliers.

“I've never had real tax strategies or a total view of how things were going,” says Sam Faillace, a consultant and Lettuce client. “Since I created my S-Corp, the …work I've been doing is suddenly a real business. I feel empowered.”

Why don’t all self-employed people have S-Corps? 

Historically, the bureaucratic requirements of setting up and managing an S-Corp have been a major barrier. Most freelancers are too busy working to deal with a massive amount of paperwork. Some financial advisors may have even told them that establishing an S-Corp was too much of a hassle. Thankfully, innovative companies looking to help solopreneurs have broken down these barriers.

Tax Help For Solopreneurs by Solopreneurs 

Powered by technology, automation, machine learning and AI, Lettuce is a comprehensive tax and accounting solution that finally makes S-Corps a realistic choice for solopreneurs. You can make more money without doing more work and take advantage of the opportunities the tax system provides. This is a real case of specialized AI technology that actually works and saves you money.

Lettuce was built from the ground up for solopreneurs by solopreneurs. The goal: to give people like you — the millions of self-employed business owners whom the tax system disadvantages — more access to specialized tax advice and automated bookkeeping and accounting technology. You no longer have to settle for the average refund. 

Through the power of proprietary machine-learning technology, Lettuce offers an accessible, efficient solution that makes the tax system work for you. So far, Lettuce has saved thousands of customers an average of $15,000 per year. 

“As a solopreneur, I can’t tell you what a relief it is to know Lettuce is on it,” says self-employed fractional CTO Brenden Grace, who was on the hunt for a simple technology solution that could handle his business setup, accounting and banking. “No more overpaying quarterly taxes. No more penalties. Just peace of mind knowing Lettuce is on the job.” 

Learn More About Lettuce Today

Have questions about your self-employment income, taxes, bookkeeping, or accounting? Check out our website, or chat with LettuceHead AI for clear, comprehensive answers, 24/7. You’ve got nothing to lose, and only time and money to gain.

Curious if an S Corp is right for you?

Try the Lettuce Tax Calculator to see how much more you can take home each year.

See your savings