A growing number of people are voting with their skills and leaving the world of traditional employment behind. These are the folks who are opening their own small businesses, the people who are embracing freelancing, and the men and women who are using gig work to make a good income.

As this trend continues, many of those newly self-employed individuals are finding themselves at a loss, especially when tax season rolls around. One of the worst feelings is working so hard throughout the year, only to get blindsided by a huge tax bill you weren’t ready for.

While traditional employees can rely on the companies they work for to withhold taxes and report their earnings to the IRS, the self-employed are expected to complete these actions on their own.

To make matters worse, the self-employed often pay higher taxes than their traditionally employed counterparts, leaving them short of the cash they need when April 15 rolls around.

If you get blindsided by a tax bill of more than $10k to the IRS or state but can’t pay in full, contact our firm today. We help people find tax relief.

If you are newly self-employed and want to avoid this fate, here are some timely tips for making your self-employment activities less taxing.

Set up a business bank account

It is important for the self-employed to keep their personal and business activities separate, and the best way to do that is with a business bank account. A basic business checking or savings account will make it easier to track your income and expenses, making tax season easier and less costly.

Open a business credit card account

Having a separate credit card in the name of your business will give you an easy way to pay expenses applicable to your self-employment income. This can make expense tracking, reporting, and tax filing a lot easier.

Avoid underpayment penalties by making quarterly payments

When you work a traditional job your employer is responsible for accurate tax withholding, but the self-employed are not so lucky. As a self-employed individual you are responsible for paying your taxes on a timely basis, and failing to do so could trigger costly penalties and interest. Making quarterly payments to the IRS and state is the best way to avoid those expensive repercussions.

Track expenses throughout the year, not just at tax time

If you wait until April to add up your expenses, you could miss deductions that would have otherwise reduced the amount you owe. Tracking expenses when they are incurred will help you avoid this underreporting, so you get credit for every penny.

Research retirement plans for the self-employed

The self-employed have access to some exceptionally generous retirement plans, including solo 401(k) plans and SEP-IRAs. These accounts can sharply reduce the amount of taxes you pay, so do your homework and choose the one that is right for you.

Have your taxes reviewed by a qualified tax professional

When your taxes are simple, doing them yourself is pretty easy. Tax software makes tax filing simple, but that simplicity could be costly when you are self-employed. Even if you are confident in your abilities, having your work reviewed by a CPA or enrolled agent could save you a lot of money.

There is a lot to love about self-employment, from the chance to work at home to the opportunity to live life on your own terms. Even so, being self-employed can be taxing, quite literally, and it is important to plan carefully from the start. The tips listed above can help you reduce your taxes, so you can keep more of the money you worked hard for.


Our firm specializes in tax resolution and helping people who owe the IRS or state $10,000 or more. We’ve seen taxpayers get blindsided every year by a huge tax bill and often fall behind on their taxes for years on end. If that’s you, we can help. Contact our firm today to discuss your tax debt settlement options.