Question: How can small business owners prepare for quarterly estimated taxes? Quarterly Estimated Taxes: Who Must Pay Them and How Small Business Owners Can Prepare When taxes aren’t withheld from your income, the IRS expects you to pay as you go. That’s where quarterly estimated taxes come in. For many small business owners, freelancers, and individuals earning income outside a traditional job, understanding these payments is essential to avoiding penalties and staying on track financially. Who Needs to Pay Quarterly Estimated Taxes Quarterly estimated taxes apply to anyone who expects to owe at least $1,000 in federal tax for the year and doesn’t have enough withholding to cover it. This most commonly includes self-employed individuals such as freelancers, gig workers, sole proprietors, and single-member LLC owners. Because no employer is withholding taxes for them, they must pay throughout the year. Partners and S-corporation shareholders also need to plan ahead. Even if profits stay in the business, owners are taxed on their share of income reported on Schedule K-1. S-corporation owners who receive wages may have some withholding through payroll, but additional pass-through income often requires separate estimated payments. Real estate investors frequently owe estimates too,