I've always gone the DIY route when it comes to my taxes. While I'd love to pay someone to do them for me and save myself the time, in the end, I trust myself more than anyone else.
In fact, as my tax situation has grown increasingly unique, I've become more pro-DIY.
I'm both a freelancer and an expat. In the past, I've had years where I worked partially from the US and partially abroad, lived in multiple states, and had both full-time W-2 work and contracted 1099 work.
In other words, my taxes have seen a lot of different situations. And through it all, there's one tax software I've sworn by.
I've used TurboTax and H&R Block, and I've looked into using TaxAct. Of the three, TurboTax is the clear winner in my book. It was my favorite when I was a full-time employee, and now that I'm a freelancer and an expat, I like it even more.
TurboTax isn't the cheapest tax software, but for me, it's the easiest and most versatile.
TurboTax and H&R Block are priced similarly, although in most situations, filing with H&R Block's software can save you a few dollars. TaxAct is cheaper than both.
That being said, price isn't the only factor worth considering, especially when price differences are so minuscule.
Convenience and ease are extremely important to me. The faster I can do my taxes, the more time I have to spend working. So in the end, a spendier tax program that saves me an hour or two on taxes is actually cheaper.
TurboTax has the most user-friendly interface of any tax software I've used, although H&R Block is a close second.
When I briefly navigated through TaxAct, I found the interface to be cluttered and confusing. I probably could have figured it out with a little extra time, but as a freelancer, I try to minimize the time and energy I spend on non-income generating tasks.
TurboTax is intuitive and easy to skip through sections that are irrelevant. Inputting my 1099 income as a freelancer is a breeze with TurboTax's Self-Employed plan, and it was also easy for me to jump to some of my more unique tax needs like the Foreign Earned Income worksheet.
Speaking of more obscure tax needs, there's one feature that clearly sets TurboTax apart from the pack for me: customer support.
While all tax programs provide live help if you upgrade to the right edition, TurboTax provides excellent, live, on-screen support for all users. Even those using the free edition get tech support via chat or phone.
The first time I had to file the Foreign Earned Income form, I couldn't find the form or figure out how to file it. Even though I'd only upgraded once and was using the Deluxe edition for $40, (a must if you're reporting 1099 income from freelance work), I was able to get a live person on the phone to walk me through where to find the form and how to file it through TurboTax.
That experience solidified my choice to stick with TurboTax. The wait to talk to a real person was brief, and the person I spoke with was extremely helpful.
On top of that, TurboTax has a massive searchable database of both help articles and user-submitted tax questions that I refer to constantly while doing my taxes.
Some of these questions are answered by TurboTax professionals while others are answered by community members. Altogether, you can find answers to just about any question you have.
Last year was the first year as a freelancer that I needed to upgrade from the Deluxe version of TurboTax to the Self-Employed version. While it was costly, upgrading got me a much bigger return as I was able to claim more deductions.
The key to getting a bigger return when you're self-employed is tracking your business expenses thoroughly throughout the year and maximizing your deductions during tax season. I use QuickBooks Self-Employed to track my business income and expenses and also to help me estimate my quarterly taxes.
Because QuickBooks and TurboTax are owned by the same company (Intuit) they offer a bundle that includes both QuickBooks Self-Employed and TurboTax Self-Employed.
If you get the bundle, you can integrate the two programs. This allows you to do things like automatically import your business expenses from QuickBooks into TurboTax and pay your quarterly taxes online with TurboTax.
I didn't buy the bundle last year because it was my first year trying out QuickBooks, and I wanted to make sure that I liked it before committing to the bundle, which is charged as a monthly subscription fee. Now that I know QuickBooks Self-Employed is the right choice for me, I'll be upgrading to the QuickBooks/TurboTax bundle.
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