Self-Employed in Florida? The IRS Expects Four Payments a Year
Self-employed in Florida? The second quarterly estimated tax payment is due June 15. Find out what estimated taxes are, who needs to pay them, and how to calculate the right amount.
You filed your taxes in April. Maybe you requested an extension. You exhaled.
But if you work for yourself, run your own business, or earn income that no one automatically withholds taxes from — the IRS is already waiting for your next payment.
And it’s due June 15.
⚠️ Key fact: The U.S. tax system operates on a “pay-as-you-go” basis. Employees do this automatically through paycheck withholding. Self-employed workers do it themselves — four times a year.
If this is the first time you’re hearing this, you’re not alone. It’s one of the most misunderstood parts of the American tax system — especially for people coming from countries where taxes work differently.
In this guide, we explain exactly what estimated taxes are, who needs to pay them, how to calculate the right amount, and what happens if you don’t.
What Are Estimated Taxes?
Estimated taxes are payments you make to the IRS during the year — before filing your annual return — to cover the taxes you’re generating as you earn income.
When you work as an employee, your employer automatically withholds a portion of each paycheck and sends it to the IRS. You never have to think about it.
When you’re self-employed, that automatic process doesn’t exist. You’re responsible for calculating what you owe and sending it to the IRS yourself — four times a year.
💡 In plain terms: Estimated taxes are like “pre-paying” part of what you’ll owe in April. The IRS doesn’t want to wait a full year to collect — it wants to receive its portion as you earn.
Who Needs to Pay Estimated Taxes?
You need to pay estimated taxes if you expect to owe more than $1,000 in federal taxes during the year and don’t have enough automatic withholding to cover it.
This applies primarily to:
• Freelancers and independent contractors (1099 income)
• Small business owners — LLCs, sole proprietors, partnerships
• Construction contractors, plumbers, electricians, painters
• Stylists, nail technicians, and beauty professionals working independently
• Gig economy workers (Uber, Lyft, DoorDash, Instacart)
• Independent sales reps or real estate agents
• People with rental income, investment gains, or significant side income
✅ Exception: If you work as a W-2 employee and your withholding fully covers your tax liability, you likely don’t need to make additional estimated payments. But if you have self-employment income on the side, that portion may still require quarterly payments.
When Are Quarterly Payments Due in 2026?
Here’s the part that catches most people off guard: the IRS “quarters” are not divided into equal three-month periods.
| Quarter | Period Covered | Deadline |
|---|---|---|
| Q1 | January 1 – March 31, 2026 | April 15, 2026 |
| Q2 | April 1 – May 31, 2026 | June 15, 2026 |
| Q3 | June 1 – August 31, 2026 | September 15, 2026 |
| Q4 | September 1 – December 31, 2026 | January 15, 2027 |
⚠️ Q2 only covers TWO months, not three. Many people pay Q1 on April 15 and assume the next payment isn’t due until September. Costly mistake: Q2 is due June 15 — just 60 days later.
How Much Do You Actually Owe? A Real Example
There’s no fixed number. What you pay depends on how much you earn and how much remains as net profit after deducting business expenses.
📌 Example: Maria runs her own cleaning business in Homestead. This year she’s brought in $40,000 in revenue.
Her business expenses (supplies, gas, equipment): $10,000.
Net profit: $30,000
Self-employment tax (15.3%): ~$4,590
Estimated federal income tax: ~$3,200
Estimated annual total: ~$7,790
Approximate payment per quarter: ~$1,948
This calculation can vary based on deductions, tax credits, and your personal situation. Having a tax professional review your actual numbers can make a significant difference — not just for one quarter, but for the entire year.
What Happens If You Don’t Pay or Underpay?
The IRS charges an underpayment penalty when estimated taxes aren’t paid on time or in sufficient amounts. They’re not catastrophic, but they add up:
• Late payment penalty: 0.5% per month on the unpaid amount
• Annual interest on the balance: approximately 7% in 2026
• If you owe more than $1,000 when filing your April return, an additional underpayment penalty may apply
Important: Not paying estimated taxes doesn’t make the problem go away. It simply delays it — and makes it more expensive.
The Connection Between Your Books and Your Quarterly Taxes
Here’s the reality many business owners discover too late:
If you don’t keep an organized record of your income and expenses throughout the year, it’s impossible to accurately calculate what you owe each quarter. You end up either overpaying or underpaying — and neither is a good outcome.
• Overpaying: you’re giving the IRS an interest-free loan
• Underpaying: you’re accumulating penalties and interest
💡 Solid bookkeeping isn’t just for tax season — it’s the tool that makes accurate quarterly payments possible, helps identify deductions in real time, and enables smarter financial decisions all year long.
At Limitless Tax, we help our clients keep their books organized throughout the entire year — not just in April — so they never have to guess what they owe the IRS.
Frequently Asked Questions About Estimated Taxes
• Do I need to pay estimated taxes if I just started my business this year?
Yes, if you expect to earn enough to owe more than $1,000 in federal taxes. You can start making payments from the quarter in which you began generating income. Don’t wait until April of next year.
• What if my income varies a lot from month to month?
You can use the annualized income installment method, which adjusts each payment based on what you actually earned during that specific period — rather than dividing the year into equal portions. It’s more complex to calculate but can help you avoid penalties when income is irregular.
• Can I pay estimated taxes online?
Yes. You can pay directly at IRS.gov using Direct Pay or the EFTPS (Electronic Federal Tax Payment System). You can also use the IRS2Go mobile app. It’s fast, free, and fully documented.
• I’m a W-2 employee but also do freelance work. Do I need to pay estimated taxes?
It depends. If your W-2 withholding is large enough to cover your freelance tax liability too, you may not need separate payments. One practical option is to increase your withholding at your main job by adjusting your W-4. A tax professional can help you determine which approach works best for your situation.
• What form do I use to make estimated tax payments?
Payments are made using Form 1040-ES. It includes a worksheet to calculate your annual estimate and payment vouchers for each quarter. At Limitless Tax, we can help you complete it accurately.
Don’t Wait for the IRS to Remind You
Estimated taxes are one of those topics most self-employed workers discover the hard way — when they already have a penalty notice or an unexpected balance in April.
The good news is that with the right guidance, the process is completely manageable. You don’t need to be an accountant to pay correctly — you need to know what you’re earning, what your expenses are, and have someone you trust help you calculate the right number.
That’s exactly what we do at Limitless Tax.
June 15 Is Coming — Let’s Get Ahead of It Together
At Limitless Tax, we’ve spent over 10 years helping freelancers, independent contractors, and small business owners in Hialeah, Miami, Homestead, and Charlotte stay compliant with the IRS — without surprises.
If you’re not sure how much you owe this quarter, or if you need to get your books in order before June, our bilingual team is ready to help.
