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The Best Tax Tips and Software for Small Businesses

Taxes haven't gotten any simpler. But with the right apps and software, filing can be a breeze.

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I thought all of my life's problems would be over once I started making money. I was in my early 20's making tens of thousands of dollars a month. Life was good. Or so I thought. 

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I didn't understand taxes at all, but I figured the money was coming in, so the rest of the stuff would work itself out, right? Not really.

I paid the price for that naivete in the form of interest, penalties and a host of other financial headaches I'd rather not be reminded of. So, don't neglect or put off your taxes like I did. It won't work itself out. You've got be proactive. 

Related: Take Advantage of These 16 Commonly Missed Tax Deductions

There is time and money involved in doing taxes. One in three businesses spend 40+ hours a year doing federal taxes, as per a 2018 NSBA Tax Survey. And it gets worse. “Fifteen percent of those businesses spend more than $10,000 a year to complete their taxes while 41 percent of small businesses spend less than $10,000 on marketing annually,” according to Gusto.


As an editor over at Careful Cents, we've covered the best tax software for small businesses in-depth, as well as how to avoid a huge tax bill when you're self-employed. But I felt compelled to share the broader strokes of my research here, with the wider entrepreneurial community, so you don't end up in the same sinking boat I was in. Like virtually all problems in life, best to get ahead of them before they metastasize. 

And full disclosure: I'm not a tax professional nor am I pretending to be one. I'm just someone who's learned much of this hard way and hope, after reading this, you won't have to.

First, two simple tax tips, then we'll get to the software itself.

Use a Separate Account to Pay Taxes. 

This is one of the simplest decisions you can make in your business life -- setup a separate tax savings account. For most banks, if you have a checking account already, you can just call and open a savings account up over the phone.

As a small business owner or freelancer, I get it, it's nice to have everything draw from one account. But when it's time to sift through and tally everything up come tax time, things can get messy. Spare yourself the headache. Make estimated tax payments straight from a separate account.

And here's how to make that even easier.

Related: TaxSlayer Offers a More Cost-Effective Way to File This Tax Season

Use Apps to Automate Tax Savings.

This is another one of those simple decisions you'll be kicking yourself for not having thought of sooner. Use apps like Digit or Acornsyou can setup up recurring withdrawals weekly, bi-weekly or whenever you get paid. And these recurring withdrawals should go straight to your tax savings account. Name all the accounts something simple (i.e., "income tax") so you aren't scrambling every April or every quarter.

Now onto the software side of things.

Best Tax Software for Freelancers.

If you file a Schedule C or 1040, TaxSlayer is a great option. There's a few reasons TaxSlayer is the best tax software for freelancers, in my opinion. Unlike TurboTax -- and more on them in a bit -- you don't have to pay $200 for all your filings or pay additional money for support. 

The functionality is similar, but it's just $47 at the federal level, an additional $29 at the state tax filing, and they have representatives available 24/7 to walk you through questions, via phone, email or live chat. Customer service is where they really shine, considering that, as a freelancer, taxes are often the last thing on your mind -- until it's time to do them, at least! But if you're disciplined about adhering to those first two tips above, and use a service like this, you won't have anything to scramble about.

Best Tax Software for Small Businesses.

TurboTax was started in 2001, eons ago in internet years -- who remembers buying the those TurboTax CDs? Although TurboTax Business might be overkill for an independent freelancer, it's a great option for a growing small business.

For instance, if you use QuickBooks, Intuit allows you to import all of that data directly. You can also TurboTax Business to manage taxes for LLCs, C-corporations, S-corporations, estates and other company structures. 

Related: Top Investment Strategies to Help You Save Money on Taxes

While most of the so-called "best tax software for small businesses" focus on filing by April 15, with TurboTax Business you can file quarterly, pay estimated taxes and even submit returns to individual states where you may owe.

The biggest downside with this? Cost. It's $169.99 and you have to pay $24.99 for each state tax return you file, plus, should you require a tax professional to assist, you'll have to fork up an additional payment. But given how robust the software suite is, it may be worth the cost.

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