Self-employment is full of perks. You can make your own hours, choose your clients, work in pajama pants, or no pants. One thing you can’t skip is paying taxes and unlike folks with regular W-2 jobs, no one’s withholding them for you. You are HR and the Accountant. Maybe you hire an accountant to help you figure out filing, that is a very solid choice for most people.

For me I like to figure out how to do things on my own. I’m cheap as heck, and if I can save a few hundred every year learning how to manage my own taxes, then I will. It was scary at first I thought if I did it wrong I might get in trouble. Taxes make us all sweat a bit. They are not exactly the easiest pill to swallow, but as the guy who frowns disconcertingly from the 100 dollar bill once said, “…nothing is certain except death and taxes”, at least if you’re not a wealthy bastard who can afford to not pay them.

I made this as the guide I wish I had when I became self-employed and had to start paying estimated quarterly taxes.

So… What Even Are Estimated Taxes?

If you’re self-employed, the IRS expects you to pay taxes as you earn income. Not just once a year. These quarterly payments include:

  • Federal income tax (based on how much you make)
  • Self-employment tax (that’s Social Security + Medicare—about 15.3%)

If you make at least $400 in self-employment income, you’re on the hook for self-employment tax. If you expect to owe at least $1,000 in total taxes, you’re supposed to pay quarterly.

The Due Dates You Need to Know (2025 Edition)

  • April 15, 2025 – Q1
  • June 16, 2025 – Q2
  • September 16, 2025 – Q3
  • January 15, 2026 – Q4

If you file your 2025 tax return and pay your entire balance by January 31, 2026, you can skip the Q4 payment. But only if you’re early and on top of it.

Safe Harbor: The IRS’s Version of “Close Enough”

Here’s the reality… the IRS doesn’t expect you to be psychic. You don’t have to estimate your taxes perfectly. As long as you follow one of their “safe harbor” rules, you’re unlikely to get hit with penalties.

You’re in the clear if you either:

  1. Pay 100% of your 2024 tax bill (or 110% if your AGI was over $150,000), or
  2. Pay 90% of what you’ll owe for 2025, even if you end up owing more in April

Pick the easier one, and aim for that in your quarterly payments.

Case Studies

1. Married, Self-Employed, Filing Jointly – $120K Income

Meet Lucas and Adrian. They’re both freelancers. Lucas’s a photographer, Adrian is a software consultant. They expect to earn $120,000 combined in 2025.

  • In 2024, they owed $14,000 in taxes.
  • To be safe, they want to hit that 100% safe harbor mark.

Quarterly plan:

  • $14,000 ÷ 4 = $3,500 per quarter

They automate $3,500 payments from a joint business savings account (more on that below). But they’re also projecting closer to $135K in income this year, so they’re planning to toss in a little extra to avoid surprises.

Smart move: They put their “tax savings” in a high-yield savings account between quarters. That extra interest? Helps cover software fees and coffee.

2. Single Freelancer – $63K Income

Meet Geralt. Geralt is a writer, working with multiple clients, and just hit their stride after a slow winter. They expect to earn about $63,000 in 2025.

  • In 2024, they paid $7,200 in taxes.
  • This year they’re aiming to pay 90% of their projected 2025 taxes, which they estimate will be about $8,200.

Quarterly plan:

  • $8,200 ÷ 4 = $2,050 per quarter

Geralt uses a simple rule: 25% of every client payment goes into a tax bucket. It’s not perfect, but it means Geralt never ends up panicking at deadline time.

Pro tip: I named my tax account ‘Daddy Governments Money’, but you might pick something like ‘IRS Troll Toll’ so to feel less bitter when you move money into it.

How to Actually Calculate It (Without Crying)

  1. Estimate your total income. Be realistic. Overestimate if you’re unsure.
  2. Subtract deductions you know you’ll take—like the standard deduction or business expenses.
  3. Use the current tax brackets to estimate your federal income tax.
  4. Add 15.3% for self-employment tax.
  5. Divide that number by four. That’s your quarterly amount.

Yes, it’s math. But it’s survivable. You can also use IRS Form 1040-ES for worksheets if you like official stuff, or use my free 2025 Estimated Tax Calculator - it walks you through everything in plain English and does all the math for you!

Tips That Actually Help

  • Automate your payments with the IRS Direct Pay tool or EFTPS. It removes the guesswork.
  • Open a dedicated savings account for taxes—ideally a high-yield one.
  • Treat tax time like a client deadline. Put it on your calendar, and don’t ghost it.
  • Track your income monthly. Use a spreadsheet, a notepad, YNAB, whatever works. Just check in.

Wrapping It Up

Paying quarterly taxes isn’t exactly thrilling, but it also doesn’t have to be a source of dread. With a little planning and some steady systems, you can handle this without surprise penalties or late-night IRS research.

Honestly? It’s part of what makes you a business owner. You’re doing the real work not just the fun parts. And every time you make that estimated payment, you’re one step closer to making tax season a footnote instead of a crisis.

~ Melon

Note: This article is for informational purposes only and does not constitute tax advice. Please consult a tax professional for personalized guidance.