The call came in March. A landscaping company owner — six employees, a solid book of clients, a business he’d spent nine years building — had just found out he owed the IRS $23,000. Not because he did anything wrong. Because no one had ever explained how quarterly taxes worked.
He’d been filing once a year, paying what he owed, and moving on. What he didn’t know was that the IRS expected him to be paying throughout the year. The lump sum he owed was fine. The penalties for not paying quarterly were not.
It’s one of the most common — and most avoidable — tax problems small business owners run into.
What Are Quarterly Taxes and Do You Actually Have to Pay Them?
If you work for someone else, your employer withholds taxes from every paycheck. Simple. When you own a business, no one does that for you. The IRS still wants its money throughout the year — they just expect you to send it yourself, four times a year, in what are called estimated tax payments.
The rule of thumb: if you expect to owe $1,000 or more in taxes when you file, you’re required to make quarterly payments. For most small business owners, self-employed individuals, and freelancers, that threshold gets crossed quickly.
Miss the payments and you don’t just pay more at the end of the year — you pay penalties on top of what you owe. That’s what caught our landscaper off guard.
The 2026 Quarterly Tax Deadlines
Mark these in your calendar. Set a reminder. Tattoo them on your wrist if you have to.
- Q1 (January – March): April 15, 2026
- Q2 (April – May): June 16, 2026
- Q3 (June – August): September 15, 2026
- Q4 (September – December): January 15, 2027
Notice that Q2 only covers two months, not three. That trips people up every year. The IRS sets these dates — they don’t flex. You can make payments directly through the IRS New Direct Pay System
How to Calculate What You Owe Each Quarter
Here’s the straightforward version: estimate your total annual income, figure out what you’ll owe in taxes for the year, and divide that number by four.
If you want a safer approach, there’s what’s called the safe harbor rule. Pay at least 100% of what you paid in taxes last year (110% if your income is over $150,000) and the IRS won’t hit you with underpayment penalties — even if you end up owing more when you file.
For self-employed quarterly taxes, you’re also responsible for self-employment tax on top of income tax. That covers Social Security and Medicare. It adds up, which is why the next section matters.
How Much Should You Set Aside?
Most tax advisors will tell you to set aside between 25% and 30% of every dollar of net profit. Some will say up to 35% depending on your state and income level.
The simplest habit: every time revenue hits your account, move a percentage to a separate tax savings account immediately. Treat it like it isn’t yours. Because technically, it isn’t — a portion of it belongs to the IRS and they will collect it one way or another.
What Happens If You Miss a Payment?
Life happens. A quarter gets away from you. Here’s the reality: missing a quarterly payment doesn’t mean you’re in serious trouble. It means you’ll owe a penalty on that underpayment when you file.
The penalty rate changes, but it’s typically a few percentage points on the amount you should have paid. Not catastrophic — but unnecessary. And if it happens repeatedly, it adds up.
The bigger risk is missing payments and also not setting money aside. That’s when business owners end up in the position our landscaper was in — a large lump sum due at once with no cash set aside to cover it.
How to Make Quarterly Taxes Less Painful
So what separates the business owners who handle this well from those who get caught off guard every quarter? They usually do three things:
They automate the savings. A percentage of every payment received goes straight into a dedicated account. Non-negotiable.
They work with a tax advisor. Not just at filing time — throughout the year. A good advisor runs projections, flags any changes in your situation, and makes sure you’re not overpaying or underpaying.
They stop treating taxes as a surprise. Taxes are a cost of doing business. Build them into your numbers the same way you build in payroll or rent.
How DCG Takes This Off Your Plate
Tax planning isn’t something that should happen once a year in a panic. It’s something that should happen continuously, quietly, in the background — so that when April rolls around, there’s no drama.
At DCG, our tax team works alongside your bookkeeping from day one. We track your income throughout the year, run quarterly projections, and make sure you know exactly what to set aside and when to pay it. And because your financial data is already with us, nothing gets missed and nothing requires a last-minute scramble.
Our landscaper is still in business. Better organized now. Quarterly payments handled. No surprises.
That’s the goal for every client we work with.
Want to get ahead of your taxes instead of chasing them? Connect with the DCG tax team.
