6 ways to make tax season easier

by Krystal Bick
March 5, 2020

13 hours.

The average American spends 13 hours working on their taxes each year. If you’re like me, and happen to not particularly enjoy pouring over spreadsheets of numbers and tax codes, then 13 hours could easily feel like eternity. Or hell. Depending on how dramatic you want to make it. And while I’m certainly not perfect at the process, I’ve learned over the past 5 years running this blog as my sole business, that tax prep can take a ton of time (often times longer than 13 hours for me!), diligence and above all, patience (with a side of really good red wine).

A lot of you noticed over the past few weeks, I’ve been setting aside specific tax prep time in my daily schedules on Insta Stories, with some of you even following up via DM for my advice on filing, especially when you can’t necessarily afford an accountant. A bit of back story: Before quitting Google over five years ago, I found an amazing accountant who truly took the time to understand how I run my blog as a business, but I want to stress, there are amazing options (like my partner today H&R Block!) if you don’t have the funds to hire a CPA (or even if you do!). Prior to hiring mine, I filed through H&R Block (my mom is a big fan and got me hooked on them when I first started filing years ago) so when their team approached me about working together on their Tax Pro Go virtual tax prep solution, I felt it could be a really great alternative to share with you all, as we’re quickly approaching April 15th. So today, with exactly 42 days before T Day, I wanted to share a few tips that have made a huge difference for me as a small business owner and how Tax Pro Go can help alleviate some of the pain of filing. (Again, for the remainder of the pain, red wine does wonders, but I digress.) I also have a discount code for their services — should you want to try them out yourself! Simply enter 56852 at checkout for $20 off your filing fee!

1. Record prep throughout the year: Have you ever started your tax filing process on April 14th only to realize your records throughout the year are a HOT MESS? Well, I sure have and I majorly regretted it. The best way to ensure this all goes smoothly, is to organize your documents as you go throughout the year, to avoid any last-minute Hail Mary situations.

Generally speaking, I try to keep a digital-only policy, with Google Drive folders dedicated to my receipts and other important tax documents. I have one master Google spreadsheet where I keep track of all payments, what 1099s/W2s are being issued for the year and from whom (with a check list when I receive them) and a running category-specific expense sheet that I try to update and maintain on a quarterly basis. However, if you’re not a fan of spreadsheets, H&R Block also offers a free, secure digital tax planning app called MyBlock that allows you to upload and capture charitable donations, receipts and other tax documents. I love that you can use this app even if you don’t file your taxes with H&R Block.

A note about expenses over $75, it’s best to have two forms of receipts, the first being a bill, with itemization of the costs and the second a proof of payment, like a bank statement, to prove you were the payer. Snap photos of receipts and immediately email them to yourself to be filed away in one of your Google Drive folders (or upload them to MyBlock). If you’re curious about what types of costs count as an expense for your business, the folks at H&R Block as part of their Tax Pro Go service set you up with an actual certified tax expert who can help answer that question. More on them below.

If your records are a bit of a mess this year for 2019 filing, try not to beat yourself up over it and instead, focus on building this record keeping framework NOW for 2020 — after all, we’re only 2 months into the new year, so you basically have a clean slate. You’ll thank yourself later.

2. Start the filing process much earlier: I cannot stress this enough. START EARLY. The earlier you start, the less stressed you’ll ultimately feel throughout this whole process, because, inevitably, hiccups happen. If you don’t proactively budget time to react to them, you might be stuck filing an extension and those penalties are never fun. I personally like to start really sprucing and cleaning up my folders late January after I’ve sent out my 1099 forms to the vendors I work with, to schedule our annual phone call to review my numbers, usually sometime right after Fashion Week in mid-February. Thankfully, we’re still a good month or so out, so I highly recommend you all kick off your tax filing ASAP to get ahead of the curve!

3. Separate business from pleasure: If you run your own business like I do, or let’s say, have a side business, record-keeping becomes exponentially easier if you have a specific credit card that only your business-related costs and purchases goes on. This will help ensure none of your personal expenses get lumped into the mix.

4. Remember post-year-end options: While most of what is reviewed for tax filing covers the previous calendar year, there are a few things, like IRA contributions that can happen up until April 15th, which will impact your taxable income. Most years, I make a contribution to my SEP-IRA right around tax time, after reviewing how much different contribution levels effect my end of year figures. If you’re curious about this, I highly recommend chatting with a tax professional, like those at H&R Block, to help assess how it’ll impact your numbers. Just be sure, if you decide to contribute, that you’re contributing for the previous tax year, in this instance, for 2019, NOT 2020.

5. Seek guidance from a professional: OK, so let’s bring in the big guns, shall we? If you’re been reading some of the above and certain numbered form names are throwing you off, fear not! It used to really scare me, too until I had someone on my side, as a resource. Of course, hiring an accountant or CPA can be costly, and may not make much sense given your particular filing situation and the complexity of it. As I mentioned above, I used to file my yearly taxes with H&R Block when I was working full time at Google, usually opting to set up an appointment in-office with one of their CPAs. The appointment would be extremely informative (I ask a lot of questions) but admittedly, it was an hour of my time that was somewhat hard to squeeze in after or before work. With Tax Pro Go, they’ve really demystified the process — and it can be handled completely online or remotely with scheduled phone calls with your assigned tax pro. I went through the steps myself — here’s a breakdown of the process:

    1. Select the tax filing situation (or combination of situations that best describes you (i.e. student, self-employed, own a business etc.)
    2. From there, you’ll be bucketed into a filing group with upfront pricing — ranging from $49 for a simple W2 to $249 for a business owner (which is the bucket I would be in). Please note, this pricing covers your federal filing. Each state filing is a separate cost.
    3. You’ll be assigned your individual tax pro — their experts average around 12 years of experience each — and you’ll upload all your necessary tax documents via their secure online portal. You can even upload documents directly from your phone.
    4. Once they’ve received all your documents, they handle the rest and prepare your paperwork for you! Average turnaround time is 5 days, at that point you review the forms and submit. If along the way, you’d like to check in with your tax pro to ask questions or clarify something, you can simply message them using the in-app messaging system or set up an actual phone call to review together.
    5. They submit your paperwork and you pour yourself a glass of red wine to celebrate!

6. Brush up on any new tax regulations and rules: As you might imagine, tax regulations change pretty often and from administration to administration, so it’s always a good idea to familiarize yourself with any new codes, laws or tax breaks that might affect you. Does this mean I expect you to be researching this yourself? Chances are, if you’re like me, reading about tax codes isn’t one of your favorite pass times so I would seek guidance from a tax professional, like the ones at H&R Block perhaps before they start working on your paperwork. Fill them in on your business and how you operate and see if there’s any applicable updates or regulations that impact you. It may sound daunting, but I promise you, once you start breaking down the steps, it gets easier to wrap your head around.

And that’s it — hopefully these tips help alleviate your tax woes! But of course, I’d love to hear your tips — please let me know if you have any in the comments below. Plus, if you’re curious to try out H&R Block’s Tax Pro Go yourself, be sure to use the code 56852 at checkout for $20 off your tax filing package fee!

This post was in collaboration with H&R Block. As always, all opinions and styling are my own. Thank you for supporting all This Time Tomorrow collaborations!

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