If you’re self-employed, running a small business, or picking up freelance gigs – there’s a good chance the IRS expects you to pay taxes four times a year.
Yep, not once. Four times.
That’s where quarterly taxes come in. And if you’re confused or stressed about how they work, you’re definitely not alone.
Today, I’m going to break it down for you in simple terms – no jargon, no fluff.
Here’s what you’ll learn:
- What quarterly taxes actually are (and why they matter)
- Who needs to pay them (hint: it’s more people than you think)
- The exact deadlines for 2025
- How to calculate what you owe – without losing your mind
- How to pay (without writing a check like it’s 1999)
- How to avoid painful penalties
And a few tips to make the whole process suck less
So What Are Quarterly Taxes, Anyway?
Think of quarterly taxes like paying your tax bill in chunks.
Instead of one giant payment in April, the IRS wants you to chip in throughout the year – every three months. It’s called the pay-as-you-go system. If you don’t have taxes automatically taken out of your paycheck (like employees do), you’re expected to send them in yourself.
That includes:
- Freelancers and gig workers
- Small business owners
- Independent contractors
- People with investments, rental income, or side hustles
Quarterly taxes are estimated payments – based on how much money you think you’ll make during the year. You’re basically telling the IRS: “Here’s a reasonable guess of what I’ll owe. I’ll pay it in four parts.”
And it’s not just income tax.
You’re also covering:
- Self-employment tax (yep, that’s Social Security and Medicare)
- Other extras like the alternative minimum tax or investment taxes, if those apply to you
Let’s say you’re a travel nurse working short-term gigs across different states. You get paid well, but no taxes are withheld. If you wait until April, the IRS will hit you with a fat tax bill – plus penalties. But if you spread it out in quarterly payments, you stay in their good graces.
Easy concept. Messy if you ignore it.
Do You Need to Pay Quarterly Taxes? Probably.
Not sure if this applies to you?
Here’s a simple rule: If you don’t have taxes automatically withheld – and you expect to owe at least $1,000 in taxes this year—then yes, you need to pay quarterly.
Let’s break that down with a few common examples:
Self-Employed? You’re On the Hook
Freelancers, consultants, and contractors fall into this group.
Whether you’re a graphic designer on Fiverr or a wedding photographer with your own LLC – no one’s taking taxes out for you.
That means you need to handle it.
Running a Business? Even a Tiny One?
Sole proprietors, S corp shareholders, and business partners usually have to make estimated payments.
If your business is turning a profit – and you’re not paying through payroll – you likely owe quarterly.
Side Hustlers, We See You
Uber drivers. Etsy shop owners. People flipping furniture on Craigslist – if your side hustle is making money and no tax is withheld, that income counts.
Travel Nurses & Locum Tenens Doctors
You earn a lot. You travel from job to job. Most of the time, your contracts don’t withhold anything.
You’re a classic example of someone who needs quarterly taxes dialed in.
Investors and Retirees
If your income comes from dividends, capital gains, or rental properties, the IRS still wants their cut.
Retired folks with significant investment income? Don’t sleep on estimated taxes.
Why Quarterly Estimated Tax Payments Matter?
If any of the following applies to you, you may be required to make quarterly estimated tax payments.
- Self-Employed Income: You work as a freelancer, contractor, or self-employed individual who receives income without taxes withheld.
- Capital Gains and Investments: You’ve realized significant capital gains from stocks, real estate, or other investments.
- Partnership Distribution: A substantial distribution from a partnership through a K1.
- Lawsuit Settlement Payout: You received large payouts from lawsuit settlements.
- Debt Cancellation Income: You received forgiveness on your previous debt such as a loan or credit card.
- Retirement Account Rollover: You performed a rollover from a pre-taxed retirement account (such as a 401k) to an after-taxed retirement account (such as a Roth IRA).
- Increased Income or Bonuses: You received significant bonuses or salary increases from your regular W-2 job.
- Equity Events and Stock Options: You had major equity events such as IPOs, tender offers, or RSU vesting with double-trigger.
- Inherited Retirement Account: You’ve received a distribution from an inherited retirement account without tax withholdings.
- Stock Option Disposal: You sold Incentive Stock Options (ISO) or Non-Qualified Stock Options (NSO) that were held for a long period of time (usually more than a year).
Keep in mind that the IRS requires taxpayers to pay taxes as the income is being earned. Failure to do so may result in underpayment penalties plus interest charges, which can add up over time.
Mark Your Calendar: Quarterly Tax Deadlines for 2025
Missing a quarterly tax payment isn’t the end of the world…
…but it can cost you.
Penalties add up fast. The best move? Set reminders and pay on time. Here’s how 2025 is shaping up:
Your 2025 Estimated Tax Payment Schedule
- April 15, 2025 – for income earned Jan 1 – Mar 31
- June 16, 2025 – for income earned Apr 1 – May 31
- September 15, 2025 – for income earned Jun 1 – Aug 31
- January 15, 2026 – for income earned Sep 1 – Dec 31
Quick tip: If a deadline falls on a weekend or holiday, it bumps to the next business day. Handy, right?
Also – this one’s big – if you’re a farmer or fisherman, you can skip all but the January payment, if you file your full return by March 1. (Not super common, but worth knowing.)
Why the Weird Timing?
You probably noticed the second payment only covers two months, not three.
That’s not a typo.
The IRS doesn’t split the year evenly. It’s quirky – but it’s what they use.
Real-World Trick
One of my clients, a freelance software developer, sets four calendar alerts at the start of each year: one month, one week, and one day before each due date. Takes 10 minutes and saves him hundreds in late fees.
Set it and forget it.
How Much Do You Owe – and How Do You Pay It?
This part trips people up.
You’ve got to estimate your tax bill before the year is over. It’s like guessing the score of a game halfway through. Tricky, but not impossible.
Step 1: Estimate Your Income
- Start with how much you think you’ll make this year.
- Include all income: freelance gigs, business revenue, side hustles, investments, whatever.
Pro tip: If you made $80K last year and expect about the same, use that number.
Step 2: Figure Out What You’ll Owe
- Use Form 1040-ES—it has a worksheet that helps you calculate income tax and self-employment tax.
- If you’re self-employed, plan for 15.3% just for Social Security and Medicare, on top of income tax.
Step 3: Divide by Four
Let’s say you estimate a $12,000 tax bill.
$12,000 ÷ 4 = $3,000 per quarter
That’s what you send in, each deadline.
Step 4: Pay It
Here are your options:
- IRS Direct Pay – Fast, free, and easy if you’re paying from a bank account
- EFTPS (Electronic Federal Tax Payment System) – Good for recurring payments
- IRS2Go App – Yep, the IRS has an app
Snail Mail – You can send a check with a payment voucher (Form 1040-ES), but… seriously, just go digital
Example Time: I helped a client, a full-time Etsy seller, set up automatic payments through EFTPS. Took 15 minutes. She hasn’t missed a deadline in three years.
Set it up once. Breathe easier all year.
What If You Don’t Pay Enough? Here’s the Ugly Truth
Think you can just guess low and figure it out later?
Yeah… the IRS doesn’t love that.
If you underpay throughout the year, they’ll charge you penalties and interest – even if you pay it all off by April.
Let’s break it down.
The IRS Penalty Rule
If you owe $1,000 or more in taxes when you file, and you didn’t make enough estimated payments during the year?
Penalty time.
It’s basically the government saying, “You should’ve paid as you earned it.”
And the longer you wait? The more you owe.
How to Dodge Penalties
There are two main ways to stay out of trouble:
- Pay at least 90% of what you owe for this year
- Or pay 100% of last year’s taxes (110% if you made more than $150,000)
Example: If you owed $10,000 in 2024, and you expect to owe more in 2025, paying $10,000 through your quarterly estimates in 2025 is usually enough to avoid penalties.
Even the IRS Gives Some Wiggle Room
There are some exceptions.
If you:
- Had no tax liability the year before
- Were a U.S. citizen or resident for the full year
- And your prior year covered 12 months
Then you might get a pass. (This helps newbies, like someone freelancing for the first time.)
But still – don’t push your luck.
I once had a client who grossed $90K freelancing, didn’t set anything aside, and waited until April. He owed $22K – including $1,800 in penalties.
We got him on a payment plan – but it wasn’t fun.
Moral of the story? Estimate conservatively and stay ahead.
6 Smart Tips to Make Quarterly Taxes Less Miserable
Let’s be honest – no one enjoys dealing with taxes.
But if you put a few simple systems in place, it doesn’t have to be a headache every three months.
1. Open a Separate Tax Savings Account
Every time you get paid, move a percentage into this account. Like clockwork.
- 25–30% is a good starting point
- Out of sight, out of mind
- Come tax time, the money’s already there
Example: I tell every new freelancer I work with to set up an auto-transfer. It’s saved more financial freakouts than I can count.
2. Use a Quarterly Reminder System
Set three recurring calendar events:
- One month before each due date
- One week before
- One day before
Add links to Direct Pay or your tax software in the event notes. Boom – your future self will thank you.
3. Estimate Higher Than You Think
Worried about overpaying?
Don’t be. If you pay too much, you’ll get a refund when you file. If you underpay, you’ll get hit with penalties.
Round up a little. It’s like tipping yourself in peace of mind.
4. Use Accounting Software or a Bookkeeper
QuickBooks. Wave. FreshBooks. Even Excel if you’re old-school.
The key is tracking everything – from invoices to write-offs – so you’re not scrambling in March.
Or better yet? Hire a bookkeeper. Especially if you’re scaling your business.
5. Adjust Payments as You Go
Making more or less than expected?
Update your estimated payments mid-year.
Example: One of my clients was killing it in Q1 and paid heavy on estimates. Q3 slowed down. We adjusted, and he saved over $3K in unnecessary payments.
6. Talk to a Tax Pro Once a Year
Even if you DIY most of it, it’s worth having a sit-down with a CPA annually.
Why?
- They’ll catch things you miss
- They can help you plan better
- They might save you way more than they cost
Wrapping Up: Stay Ahead, Stay Sane
Quarterly taxes might sound like a chore – and yeah, they are – but they’re also the key to avoiding nasty surprises in April.
Here’s what you learned today:
- What quarterly taxes are and why they exist
- Who needs to pay them (spoiler: probably you)
- When they’re due in 2025
- How to calculate and actually make your payments
- What happens if you underpay (don’t)
- And a few easy tricks to stay on top of it all
If you treat quarterly taxes like just another business task – something to automate and schedule – they stop being stressful.
Plan ahead. Pay on time. And if it still feels overwhelming? Bring in a pro to help out.
No shame in outsourcing your peace of mind.