Working for yourself is exciting—you're your own boss, setting your own schedule, and building something you're proud of. But when it comes to taxes, things can get a little tricky. Unlike traditional employees who have taxes withheld from their paychecks, self-employed individuals are responsible for managing and paying their own taxes throughout the year. That’s where estimated taxes come in. They help you avoid a surprise tax bill (or penalties) when tax season rolls around, and they’re a big part of staying compliant and financially healthy as a business owner.  Let’s break down how estimated taxes work and what you need to do to stay on top of them. What Are Estimated Taxes? Estimated taxes are payments you make to the IRS throughout the year on income that isn’t subject to withholding. This includes money you earn from freelancing, gig work, contract jobs, or running your own business. If you expect to owe at least $1,000 in taxes for the year after subtracting withholding and tax credits, you’ll likely need to make estimated payments. These payments cover both your income tax and self-employment tax (which includes Social Security and Medicare). When Are Estimated Taxes Due? Estimated tax payments are made four times a year: - April 15 – for income earned January 1 to March 31 - June 15 – for income earned April 1 to May 31 - September 15 – for income earned June 1 to August 31 - January 15 (of the following year) – for income earned September 1 to December 31 If the due date falls on a weekend or holiday, your payment is due the next business day. How Much Should You Pay? There are a couple of ways to figure this out: - Safe Harbor Method: If your income is similar to last year’s, you can avoid penalties by paying at least 100% of last year’s tax liability (or 110% if your adjusted gross income was over $150,000). - Current-Year Estimate: If you expect to earn more or less than last year, aim to pay at least 90% of what you’ll owe this year. You can use IRS Form 1040-ES and your prior year’s return to help calculate your estimated payments. How to Make Payments You have a few options when it comes to sending in estimated tax payments: - IRS DirectPay – an easy way to pay online - IRS2Go mobile app – convenient for on-the-go payments - Mail a check – using Form 1040-ES - IRS online account – track payments, balances, and access past tax records No matter how you pay, be sure to mark your calendar and avoid missing a deadline. What If You Don’t Pay Enough? If you underpay or make late payments, the IRS may charge you a penalty. For 2025, the interest rate for underpayment is 7% plus 3 percentage points, and the interest is compounded daily, which can add up quickly. You can usually avoid this penalty if: - You owe less than $1,000 when you file, or - You paid at least 90% of your current year’s tax bill, or - You paid 100% of your prior year’s tax (or 110% if your income was higher) Reassess When Life Changes Life happens—maybe you got married, took on a second job, or had a child. Any of these events can change how much tax you owe. Check in on your income and expenses every few months and adjust your estimated payments if needed. If you also earn W-2 income, consider increasing your withholding through your employer by submitting an updated Form W-4. This can help offset your self-employment tax and reduce what you need to pay quarterly. Why Hiring a Bookkeeper Can Make a Big Difference Being self-employed means wearing a lot of hats—and tax planning doesn't have to be one of them. A professional bookkeeper can help you stay organized, track your income and expenses, and make sure your estimated payments are accurate and timely. At Keep-On-Booking, I work with self-employed individuals and small business owners to take the guesswork out of tax season. From ongoing bookkeeping to estimated tax support and financial reporting, I'm here to help you stay on top of your finances—so you can focus on doing what you love.
Schedule a consultation today and let’s make your next tax season the easiest one yet!

As a Colorado business owner, one of the most important decisions you’ll make is how to classify the people who work for you. Are they employees or independent contractors? Properly classifying your workers in line with Colorado's laws is crucial, as it affects everything from wages and benefits to tax responsibilities. This blog will walk you through the key differences between employees and independent contractors in Colorado, the protections each group is entitled to, and the consequences of misclassification. Whether you’re starting a new venture or managing an established business, getting worker classification right is essential for staying compliant and protecting your business. Employees: Wages and Hours: Colorado employees are entitled to at least the state minimum wage, which adjusts annually. They are also covered by the Fair Labor Standards Act (FLSA), which requires overtime pay at 1.5 times the regular rate for any hours worked over 40 in a week. Benefits and Protections: Employees have access to a range of benefits such as unemployment insurance, workers’ compensation, and health benefits. Additionally, they are protected from workplace discrimination, unsafe working conditions, and wage theft under both federal and state law. Legal Recourse: If their rights are violated, employees can file complaints with the Colorado Division of Labor Standards and Statistics. These violations could include unpaid wages, workplace safety issues, or employment discrimination. Independent Contractors: Flexibility: Independent contractors in Colorado typically enjoy more freedom in choosing their working hours and methods for completing tasks, allowing for greater flexibility in their work-life balance. Limited Protections: Unlike employees, independent contractors aren’t entitled to minimum wage, overtime pay, or benefits such as unemployment insurance and workers' compensation. They also aren’t covered under most employment discrimination laws. Tax Responsibilities: Independent contractors must manage their own taxes, including self-employment tax, and are responsible for covering their own benefits, insurance, and retirement savings. The Importance of Proper Classification In Colorado, workers are generally presumed to be employees unless proven otherwise. If an employer wants to classify someone as an independent contractor, they must demonstrate that the worker is: Free from the employer’s direction and control in performing their work; and Engaged in an independent business or profession related to the work they perform for the employer. Employers cannot rely solely on issuing a 1099 form to classify someone as a contractor. A written contract is required, outlining key elements like the contractor's obligation to handle their own taxes and the fact that they won’t receive unemployment insurance unless they or another entity provide coverage. Key Factors to Determine Worker Classification Colorado uses a variety of factors to assess whether a worker is an employee or an independent contractor. These factors include: Control Over Work: If the employer dictates how, when, and where the work is done, the worker is more likely an employee. Nature of the Work: If the worker performs tasks integral to the employer’s core business, they are probably an employee. Payment Method: Employees are generally paid by the hour or on a salary, while independent contractors are paid per project or job. Tools and Equipment: Employees often use tools and equipment provided by the employer, whereas independent contractors provide their own. Consequences of Misclassification Misclassifying an employee as an independent contractor to avoid paying overtime, unemployment taxes, and other benefits can lead to serious penalties. Businesses found in violation could face: Back pay for unpaid wages and overtime Fines and penalties Back taxes for unemployment insurance and other withheld benefits Proper classification of workers is essential to avoid legal and financial repercussions. Colorado’s Division of Labor Standards and Statistics can investigate claims of misclassification, and violations can be made public under the state’s Wage Theft Transparency Act. Get Professional Help For small business owners, navigating these complex classifications and ensuring compliance can be overwhelming. By hiring professional bookkeeping services, you can ensure accurate worker classification, maintain compliance with employment laws, and avoid costly penalties. Keep-On-Booking's expertise in payroll management, tax filing, and financial reporting allows you to focus on growing your business with confidence and peace of mind. Contact us today to learn more: https://www.keep-on-booking.com/consultation