Article Summary: HAR's "Estimated Quarterly Taxes Guide" for 2025 takes the sting out of tax time. It covers current tax deadlines, how much you should pay for quarterly taxes, and how to file. Oh yeah, we also have Quarterly Tax Reminders and a Tax Organizer if you fancy a few extras!
When I first started Host Agency Reviews, I found estimated taxes to be hard to wrap my head around. It was something completely new to me.
Having always been an employee who received a refund on my taxes, as business owner, I was freaked out that I not only had to pay taxes, but that I had to pay so much, so often. (Helloooooo sticker shock.) Business owners have to deal with enough bureaucratic bushwhacking without venturing into IRS territory more than necessary! So, let try to save you a trip to the IRS.gov site and break down estimated quarterly taxes in lay-speak.
Most people are familiar with the tax system from an employee standpoint. You have taxes taken out of your paycheck and file your returns by April 15th 2025.
Potentially unbeknownst to you, your employer doing more tax legwork in secret. Remember that w-4 you fill out when you started a job? Employers used it to figure out how much to take out of each paycheck for good 'ol Uncle Sam. As an employee, you just filled out that form and forget about it until it was time to do your annual taxes.
You employer, however, was responsible for setting aside tax money (both your portion and their portion) to pay it in a timely manner. Now that you're the business owner, you’re in charge of making sure Uncle Sam gets the money he’s looking for. That means you get to pay these things called estimated taxes.
While estimated taxes may seem complicated, they’re really not. The big idea is that you, as a business owner, generate income. And income is subject to taxes.
Think of it like this, when someone owes you money, you don't want to wait a full year to get it. The IRS doesn't want to wait a full year either. As it happens, a quarterly payment plan seems to please the IRS.
And that’s really what estimated quarterly taxes are. Now that you’re a business owner, you're responsible for setting aside the money and paying estimated taxes on a quarterly basis.
Essentially, your estimated taxes are a combination of what you owe for income, Social Security, and Medicare taxes. The taxes you now pay as a business owner are called a "self-employment" tax"
When you pay you first round of quarterly estimated taxes, you might have some sticker shock when it comes to your tax price tag. How do you avoid this sticker shock?
Here's a few things to help manage expectations:
You could very well owe 25% of your earnings or even upwards of 40% depending on your income bracket and state tax levels.
Understand that, as a business owner, you're essentially taking on the role of employee and employer (rather than splitting it down the middle). The 15.3% self-employment tax will be above and beyond the income tax you've always paid as an employee. You could very well owe 25% of your earnings or even upwards of 40% depending on your income bracket and state tax levels. That, my friends, is why you should prep yourself for sticker shock.
Amidst this depressing news, here’s a bright spot to keep in mind. Remember that you get to deduct half of your self-employment taxes when you file. Small joys, people. That’s all we can shoot for. :)
Now that you know what estimated taxes are, how in the world do you figure out how much you owe? Good question.
You can take one of two approaches:
If you’re brave, you can fill out the 1040-ES worksheet and that will help you figure out your estimated quarterly taxes. As the IRS states so casually, “To figure your estimated tax, you must figure your expected adjusted gross income, taxable income, taxes, deductions, and credits for the year.”
Uh… yeah. I’ll get right on that.
I’m a die-hard DIYer (as are many entrepreneurs). But seriously, we’re in travel. I think it’s safe to say that our love of crunching data is not why we got into the biz. My advice? Find a good tax advisor and become best friends.
Mine charges $75/hr and she is worth her weight in gold. Kinda like how travel agents are worth their weight in gold when you find the right one.
We chat with a travel-industry-specific CPA in our travel agent travel expense article if you want a launching point for your search.
While the lion’s share of your estimated tax payments will go to the Feds, remember you may also need to pay in estimated taxes to the state.
P.S. There is a small chance you may not need to pay estimated taxes as a self-employed person. Here’s a few exceptions to the rule.
You pay estimated taxes four times a year (quarterly). The due dates may vary by a few days every year due to weekends but typically you pay in on the 15th of April, June, September, and January. If due date falls on a Sat., Sun., or legal holiday, then due date is next day that is not a Sat., Sun., or legal holiday.
We want to help you with precious brain space . . . sign up below to get quarterly tax reminders from HAR! We'll send you the reminder two week before the due date to get it on your radar!
There are a couple of ways to pay your federal quarterly estimated taxes:
Visit www.directpay.irs.gov (easiest) or www.eftps.gov/eftps and set up online payments. Want more details? Here's more info on paying your quarterly estimated taxes online.
If you want, you can apply your tax refund to future quarterly tax payments. There's no right or wrong answer. It just depends on what you prioritize . . . getting your payments out of way early, or making sure that your tax return marinates in your bank account to earn as much interest as possible.
The IRS does not recommend paying your taxes by mail. At every turn, they warn against it. To make matters more complicated, they warn you not to use the address shown in the Instructions for Forms 1040 and 1040-SR. Weird and 100% counterintuitive.
Are you a thrill-seeker? You want the satisfaction of dropping your taxes in the mail slot? The address you need to send your estimated tax payment will vary by state and by form. Read more details on how to find the correct address for you.
Fun Fact: If your IRS payment exceeds $100,000,000 (did I get enough zeros in there to hit a100 million?) then you cannot pay by mail.
If you’re dying to talk to someone at the IRS (weird, but to each their own) you can call in your payment. Here’s a link to more info on paying by phone.
When it comes to how you can pay at the state level, you’re going to have to do a little digging on your state’s tax site. It's the Wild West out there!
Right now, for the tax year 2025, it's directly tied to how much you underpaid. Now, finding the exact amount for how much you owe? Good luck on that one.
There isn't really an estimated taxes penalty calculator but you can figure it out a few ways:
You know we like to go the extra mile. We've got a few goodies for travel advisors to help you along with your taxes.
Below is a beauteous Tax Organizer to help you get your ducks in a row. The form includes travel-agent-specific categories from general office expenses, to travel expenses. Take a look (then download it below!)
Interested? You can subscribe and download below!
Any small business owner can write off travel expenses, but dang there are a lot of rules. Even more, it gets. more complicated for travel agents when travel for work can get a little fuzzy with travel for leisure. This article on which travel expenses you can (or can't) write off, will make it smooth sailing!
This spreadsheet allows you track business travel expenses trip by trip to save you a few tears when it comes time to get documentation to your bookkeeper or accountant! (You need a free Airtable account to use the template!)
I'm not a tax expert but I am a business owner that wished I'd had a guide to navigate estimated taxes my first time around! So, while I'm waiting for the snow to melt here in Minnesota, I decided to write up a guide on estimated taxes—I hope it helped! If it did, I'd love it if you'd give it a like/share or share your experiences below.
Editor's Note: This article was originally published March 3rd, 2014. We update this article annually with the latest information on estimated taxes. The article was most recently updated and republished on date listed above.