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The six most common tax problems for gig economy workers

7 min read


7 min read


Gig economy jobs have boomed in recent years, becoming a way of life for so many Americans. With new business opportunities from companies such as Uber, Airbnb, and DoorDash, taxpayers are finding it easier than ever before to work for themselves.

As workers take on these new gig jobs, they’re probably not thinking of what gig economy work means for their taxes.

Whether you’re taking on a gig job as a temporary worker, or planning to work as a contractor ongoing, it’s important to understand these tax nuances.


Have questions about how gig work affects your taxes?  Check out our Guide to Independent Contractor Taxes.


Gig economy jobs turn workers into small business owners

Many people are surprised that as an independent contractor, they actually own a small business in the eyes of the Internal Revenue Service. And small businesses have extra tax rules – and potentially more IRS audits and notices. This is true whether your gig economy job is your primary source of income or your side hustle.

It’s important to know that filing taxes as an independent contractor can get complicated. You’ll usually have more requirements to file and pay taxes. That means things like:

  • Quarterly estimated tax payments
  • Payroll tax deposits and filings
  • Reporting payments to contractors each year
  • Reporting sales tax
  • State and local licensing requirements

Because of all these rules, you’ll interact a lot more with the IRS and your state. And, these tax authorities are much more likely to question you.

The 6 most common problems when filing taxes as a self-employed worker

1. “I didn’t know I had to pay self-employment taxes.”

This is a common miss for people who are newly self-employed. Whatever term you use (independent contractor, freelancer, or gig worker), you’ll have additional tax responsibilities when you’re self-employed.

You may be surprised when you file a return and find out that, on top of your income taxes, you’ll owe another 15.3% tax. This is called self-employment tax and it covers Social Security and Medicare taxes. It can result in a large tax bill if you didn’t know about it.

If you were a traditional employee, you’d pay half of this amount, and your employer would pay the other half. As a self-employed person, both are your responsibility. On the bright side, a special tax deduction for independent contractors (self-employed individuals) lets you deduct half of your self-employment tax to offset your income.

2. “I didn’t know I had to pay throughout the year.”

Instead of having taxes automatically withheld (like employees do), self-employed people have to send in tax payments four times a year (called estimated tax payments).

If you didn’t know or forgot about sending in your quarterly payments, the best time to learn about estimated payments is now. But take note: missing these payments for several months may mean you’ll owe a big tax bill plus likely penalties when you file.

If you can’t pay, you can ask for an extension or set up a monthly payment plan (called an IRS installment agreement) when you file.

3. “I keep getting behind in paying taxes.”

Self-employed people sometimes get behind in paying estimated taxes. When they do, they often file and end up with large tax bills they can’t pay.

If you already have a payment plan with the IRS but then file, owe and fail to pay, you could be considered as defaulting on your agreement. You’ll spend more money to set up a new installment agreement, owe more penalties and interest, and interact more with the IRS. If you owe tax on a later return, you can potentially add it to your current installment agreement, but again it is likely more penalties and interest would be assessed.

If your tax bill adds up to more than $50,000, there are other consequences. The IRS may ask for more information about your financial situation to set up a payment plan.

The IRS may also file a federal tax lien, which typically hurts your ability to get credit.

4. “I didn’t report cash payments.”

Depending on the type of job you have, the IRS may receive copies of forms that validate your income – such as Form 1099-NEC or Form 1099-K. However, many small businesses, especially gig workers who operate in cash, are on the honor system for reporting their income.

And with cash-intensive businesses, the IRS has few, if any, Forms 1099 to validate the income. It makes sense then, that every IRS audit of small businesses starts with scrutiny about whether the business reported all its income.

5. “I ‘wrote off’ personal expenses and I don’t know what expenses are deductible.”

This is another major area where the IRS looks at in small business audits.

New small-business owners often deduct certain expenses, like cars, cell phones, in-home offices, and travel and meal expenses. But the IRS views many of these expenses as personal (and not deductible) – unless you can prove that the expenses were business-related.

The most important thing to know – not all expenses are deductible. Just because you incur a specific expense, does not automatically mean it is deductible. The expense must be both:

  • Ordinary and necessary
  • Directly related to the trade or business

Luckily, the right guidance can steer you in the right direction. An expert tax pro can help you find allowable business deductions to reduce your taxable income as a gig worker. Find a tax pro by you.

The takeaway: Keep excellent records.

6. “I didn’t file on time (or, at all).”

Many small businesses put off filing because they can’t pay their taxes. Procrastinating like this causes many businesses to run up large tax bills and penalties. The failure to file penalty is 5% per month (or partial month) that the return is late, for a maximum penalty of 25%. If you file your return more than 60 days late (including extensions), the minimum penalty is 100% of your unpaid tax or $485, whichever is smaller. As you can see, it’s better to file on time even if you can’t pay right away.

As mentioned above, the IRS receives information about your income through various tax forms. For example, in recent years, the IRS has identified many non-filers with Form 1099-K, which reports payments the business receives from debit/credit cards and third-party processors.

Many online-retail small businesses in particular are now having to reconcile their revenues to this form. Gig economy workers who don’t file taxes and receive this form are experiencing IRS delinquent-filing notices and IRS enforcement actions.

Gig economy taxes are always on: Here’s where to get help

If you’re a business owner, including an independent contractor in the gig economy, taxes should be something you’re on top of all year long.

Start with keeping good records, making estimated tax payments to limit your tax balance when you file, and always filing an accurate return at the end of the year.

Filing self-employed taxes

When you’re ready to file your taxes as an independent contractor, you can rely on H&R Block to be there for you.

With H&R Block, you can file your taxes confidently knowing you’ll get your max refund – or you’ll get your money back. We’ll help you find all the personal and business deductions you’re entitled to.

Check out these filing options:

  • H&R Block Online Deluxe for independent contractors with no expenses to deduct.
  • H&R Block Online Premium for independent contractors with expenses to deduct.
  • Need a little help along the way? Don’t worry, with options such as Online Assist, the help of a knowledgeable tax expert is never far away.

Getting help with IRS audits and notices

Small-business owners may continue to see more of the IRS after filing. Knowing your requirements and preparing for more IRS interaction (and potentially scrutiny) is the key to minimizing tax surprises for small-business owners.

If you’ve run into any of the six most common tax traps, a tax pro can get to the bottom of your issue and even fix it with the IRS for you. Learn how it works with H&R Block’s Tax Audit & Notice Services.

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