don't mess with the IRS: how to file your estimated taxes

a quick guide on paying your estimated taxes

You create beautiful and amazing masterpieces using your words, images, and everyday life as your muse. You are not short on passion to make your dreams a reality.

But, yes there's a but, as a creative, you would rather not deal with the boring, mundane, and confusing world of business taxes.  

There're people out here in the world that enjoy this part of business (like Moi) and are happy to help you navigate the financial maze. 


business is not a hobby

You have been working hard on your business to make sure it functions as a business (read as turning a profit) and not a hobby. I am certain at least some of you have heard horror stories about the IRS labeling your business a hobby because you were not showing an income for 2 out of 5 years. 

Now you are ready for the next stage.

**dun dun dunnnn**

Paying estimated taxes quarterly!

Here's what the IRS says

"Taxes must be paid as you earn or receive income during the year, either through withholding or estimated tax payments. If the amount of income tax withheld from your salary or pension is not enough, or if you receive income such as interest, dividends, alimony, self-employment income, capital gains, prizes, and awards, you may have to make estimated tax payments. If you are in business for yourself, you generally need to make estimated tax payments. Estimated tax is used to pay not only income tax but other taxes such as self-employment tax and alternative minimum tax.

In plain English, that means you must pay taxes, and if you are self-employed, you do not have anyone to withhold taxes on your behalf (like an employer), so you have to send the taxes yourself.

Easy-peasy, right? Let's keep going.

What Does Self-employment Tax Go Towards?

When you pay self-employment taxes, you are paying into Social Security and Medicare. You are paying the same taxes as if you were an employee except you are paying the employee and employer portions. 

The self-employment tax is broken down like so:

  • 12.4% for Social Security (only the first $118,500 of earnings is subject to social security)
  • 2.9% for Medicare 
  • 15.3% tax rate

The self-employment tax is in addition to ordinary taxable income, so you may have a situation where your regular tax is $1,000 then you would owe an additional $153 in self-employment tax. Lucky for you, the IRS decided to be a little helpful. You can take half (50%) of the self-employment tax as a deduction against your income.


entity choice matters

I would totally not be serving you if I did not bring up entities and how they play a huge role with your taxes. 

There are three primary business structures majority of small business owners, creatives, and entrepreneurs use. 

  • Sole Proprietor
  • LLC (Single-member/Multi-member) 
  • S-Corporation

Sole Proprietor

include independent contractors, freelancers, and any business you are operating yourself and haven't created a separate entity. Sole proprietors file business income on their personal return by adding a Schedule C with their Form 1040. Self-employment tax is calculated from the net profit (income - expenses) shown on Schedule C. Information from the Schedule C is used to populate Schedule SE which will show your self-employment tax due. T

Single Member LLCs

are classified as a sole proprietor. The same rules apply as above.

Multi-Member LLCs

are taxed as a partnership by the IRS. They are required to file a Form 1065. Each member will receive a Schedule K-1 with the individual member's share of profit/loss and amount subject to self-employment tax. 


is a corporation with S status. The S-corp will file Form 1120S and is required to provide each shareholder and board member a Schedule K-1 showing their basis (how much money they have invested in the business) and any amounts subject to self-employment tax. 

Why You Should Pay Attention to Estimated Taxes

  • The IRS requires taxes to be estimated and paid quarterly if the net profit from your business is at least $400. The net profit calculation subtracts business expenses from business income (income - expenses = net profit).
  • If you fail to send estimated tax payments and your balance due at tax time is greater than or equal to $1,000 then you will be penalized. Of course, the calculation is a long unnecessarily complicated formula. The majority of DIY tax prep, big box, and professional tax software will automatically calculate the penalty. 
  • You are forced to stay on top of your books. You do not want to send the IRS way more money than what they are entitled too. So unless you are ok with that, you will be forced to check-in with your books at least quarterly to see if you need to make any adjustments to your estimates.  

putting it all together (step-by-step)

Here are all the steps to go about calculating your taxes. If you rather outsource this task to your accountant (kudos to you), you should still have a basic understanding of what's involved in case the need to make any last minute adjustments arises such as you landing an important contract worth major bucks.

  1. At the very least, review your books quarterly. Make sure everything reconciles and is up-to-date. With your accounting system in place, this should not take you longer than an hour.

  2. Run a profit and loss report for your business(s)
  3. Plug your numbers into the Estimated Tax Calculator ( and print (or save to Evernote or the cloud or wherever) the results
  4. Add the quarterly payments in your accounting system as a bill with a due date matching the quarterly due dates. 
  5. When the time comes you can send your payments online via, pay by phone, mail, or direct debit using EFTPS. Visit for all the details. 
  6. Update your accounting system after payment with a copy of the receipt and transaction details. You could also use a handy dandy spreadsheet to capture all the deets. 

The Wrap Up

I hope I did not bore you to death, and you learned a thing or two about estimating your taxes. My final two tips are;

Be proactive! If you fail to plan, plan to fail, or pay the IRS more money than you should.

Always. Always. Always mind your numbers. Even if you outsource your accounting, bookkeeping, and taxes you should still know, understand, and love your numbers. 

Now go forth and create!