How to File Self-Employment Taxes: A Step-by-Step Guide

Some nightmares are common:

You’re late for a flight. 

You’re unprepared for a test.

You forgot to do something important.

On a completely related note/nightmare, taxes are due on April 15th. Have you started getting ready to file?

Deep breaths: It’s going to be okay. 

Even if you’re reading this a few days before the deadline, you can condense the steps below and still file in time. And if you really can’t get it together by April 15th, don’t panic. You can always file for an extension with the IRS. Follow this step-by-step checklist to get your taxes done – and hopefully minimize the amount you have to pay.

What to do 14 days before the deadline

Figuring out how to get your taxes done at the last minute is basically the most boring choose-your-own-adventure book that was never written. But you do need to make decisions! 

File your own taxes if:

• Your tax return is simple: you have one source of income and few deductions. Most freelancers have more than one client and qualify for several deductions.
• You’re worried that it’s too close to the filing deadline to get an accountant to do it for you. 

A good next step is to download tax software. And just because you’re doing your taxes alone doesn’t mean you can’t get help. Here’s why:

• You may qualify for one or more free online filing options, depending on your adjusted gross income (AGI) and the complexity of your return.  
• If you don’t qualify for one of the free options, you’ll need to use paid tax software. For people who need a lot of assistance, TurboTax Self-Employed allows you to speak one-on-one with a Certified Public Accountant or an Enrolled Agent and ask questions before filing your return online.  

Hire an accountant if:

• You’re full-time freelance for one client or a contract worker with multiple clients and have business expenses. Your accountant will navigate your complex tax return and find every tax-reducing deduction possible. Plus, the tax preparation fee itself is tax-deductible.
• You don’t have time to do your taxes. In 2018, the average business taxpayer spent 19 hours preparing their own returns, according to the IRS. Today, it’s estimated to be at least 24 hours. 

If you decide to hire an accountant, you should:

• Use the Directory of Federal Tax Return Preparers to find a tax professional in your area. The directory allows you to search by location and also by credentials. Protip: there are plenty of accountants that specialize in working with freelancers! That means they’re dialed-in to elements of the tax code that are especially relevant for solopreneurs. For example, the CPA and founder of Little Fish Accounting has tips on how to get your small business set up for success this year, and the CPA behind Medows CPA has info about the changes to the 1099-NEC.
• Once you’ve found a pro to work with, electronically send them your documents ASAP. 

What to do 9 days before the deadline

Collect the following documents that detail your income and expenses.

Income documents

We wrote an in-depth explainer on 1099s here, but here’s a good recap. 

These are the 1099 forms contractors need to know about:

1099-NEC 

• NEC stands for Nonemployee Compensation
• you’d receive this form if you were paid at least $600 in 2025 via a platform like Wingspan

1099-MISC

• you might receive this form if you were paid for providing licensed clinical services (for example: you are a doctor, dentist, therapist or psychologist)

1099-K 

• you’d receive this form if you were paid over $20,000 and had over 200 transactions through an app like Paypal or via credit cards (you can read more about this form in our explainer)

If you haven’t received these forms from a client, don’t worry: you don’t need a physical copy to do your taxes. You just need to know how much money you made from each client last year; you’ll then share those amounts with the IRS when you file. 

Expense documents

‍A tax deduction reduces your taxable income, which, in turn, reduces the amount of tax you pay. A tax professional can determine which deductions you should claim. If you’re filing independently, here are four common categories of deductions you might take for your business.

• Travel costs
  If you drive to a job site, you can potentially deduct mileage, tolls and parking fees
• Home-office costs
  Deduct a portion of your rent or mortgage interest and real estate taxes, as well as utilities
• Education expenses
  Deduct some or all of the cost of classes and certifications that are relevant for your work
• Equipment and supplies
  Deduct part or all of the cost of the tools you use to run your business

For a more detailed list of deductions for self-employed workers, check out this handy guide from Susan Lee, an Enrolled Agent and Certified Financial Planner Professional.

What to do 3 days before the deadline

It feels good to get things done, and it feels extra good to get your taxes done. All you need to do now is file!

If you’re filing taxes by yourself:

• Use tax software to complete your return.
• The software will submit your return directly to the federal and state governments through IRS’s e-File option. Download your tax returns, and save it for three years.

If you’re using an accountant:

• Review your tax return within your accountant.
• Your accountant will file your tax return electronically.

If you owe, make sure to pay using one of the methods recommended by the IRS.

What to do one week after filing your taxes

Now that you’ve slayed this tax beast, get ahead to save time, money, and headaches the next time tax season comes around. Here’s three actions you can take to help yourself in the future:

1. Consider paying estimated quarterly taxes. Paying quarterly taxes saves you from the shock of a big year-end tax bill, and it will help you avoid a penalty. Here’s the updated 2026 schedule for quarterly tax payments.
2. Claim every deduction and keep an eye on your profit and loss statement. 
3. If you get paid through Wingspan, our free Tax Withholding feature can also make your next tax time easier! It automatically deducts funds from each payment based on an estimated tax rate you’ve chosen, and stores those funds safely in a separate account for free. When you’re ready to pay the IRS, it takes one click to send the funds. You can set it up in minutes, right here.

Now that you’re all squared away on taxes, take a second to use these free apps to help supercharge your business. 

This information is not intended to provide, and should not be relied on for, tax or legal advice. Wingspan is a financial technology company, not a bank. Banking services are provided by Lead Bank, Member FDIC. Deposits are FDIC-insured through Lead Bank, Member FDIC. The Wingspan Visa® Debit Card is issued by Lead Bank, Member FDIC, pursuant to a license from Visa USA Inc.Your funds are FDIC insured up to $250,000 through Lead Bank.; Member FDIC.