5 Must-Have Tax Tools for Freelancers

Taxes: one of the most dreaded words in the history of freelancing. When you’re self-employed, you’re not only expected to pay taxes to Uncle Sam on a quarterly basis, but you’re also responsible for keeping track of your business expenses and determining how much you can deduct.

The good news is there’s software that makes managing your taxes as easy as if you had an employer doing the dirty work for you. By taking advantage of these tools, you’ll make dreading tax day a thing of the past.

And Co

Say goodbye to the shoebox full of receipts. Just connect your bank account to And Co, and the app automatically tracks, reconciles and categorizes all of your business expenses. Having an organized expense report for your accountant saves them time, which saves you money.

And Co also helps you create and send invoices, receive payments from clients, and generate income statements. You even get your own “Chief Operator” (an actual human) who’s there to consult you at every step of the way.

99 Deductions

When working with a tax accountant isn’t in your budget, 99 Deductions is the perfect tool to make sure you’re not missing any deductions. Start by checking out the most common deductions for your line of work. You can click on each one to get a breakdown of exactly what’s required to qualify. You can also search by different types of deductions.


The most important part of being prepared for tax day is having enough money to pay your bill. Painless1099 automates the entire process of saving and sending money to the IRS through a smart bank account.

When you sign up for Painless, clients can send your payments directly to your Painless1099 account. The amount you owe in taxes is automatically withheld from each payment, and the remaining balance is deposited into your regular checking account. When it’s time to pay your quarterly estimated taxes, Painless makes payments to the IRS directly from your tax account.


The last piece of the puzzle is actually filing your taxes. TurboTax is a great tool for navigating this process. Easily upload bank documents and fill in any other relevant information through their online interview. Once your return is ready to be shipped, TurboTax does one last check to make sure you’ve taken advantage of all possible deductions. They even let you know if you’re at risk of being audited and share some quick tips for reducing that risk.

CPA for Freelancers

If you’re already behind in the year and really need to work with a professional, check out CPA for Freelancers. They offer a great team of professional CPAs who can help you get your taxes filed and receive a fast, clean return. They can also answer any tax, accounting or financial questions you have about your business. If you’re simply looking for helpful resources, their website has a comprehensive tax guide available for free.

Painless1099 automates saving for self-employment taxes so you can focus on the work that really matters. Learn more at Painless1099.com.

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