2019 Tax Preparation Checklist

2019 Tax Preparation Checklist

As we close out 2019, you should already be preparing your business tax documentation and working in tandem with your accountant. But lo and behold, you’ve probably been too busy running other aspects of your business — scaling your company, developing new products and services or working on creating greater efficiencies and streamlining processes — to stay on top of your bookkeeping and taxes.

When it comes to a tax preparation checklist for 2019, what exactly needs to be on your to-do list? And how can you best streamline?

Here’s a tax prep checklist to get things in order for tax season.

Make Sure Your Books Are Balanced

To make sure you file your taxes correctly and aren’t overpaying, your books need to be accurate and up to date. If you’re going the do-it-yourself route, look over your transactions and books.

Not properly categorizing your business transactions means that tax-deductible expenses might go overlooked. In turn, you might end up paying more in taxes. What’s more, having unorganized bookkeeping could mean more headache and time and money wasted when it’s time to file your taxes.

Beyond taxes, unbalanced books means you don’t have the data you need to make smart, informed decisions on how to run your business.

Give Your Accountant Access to Your Books

If you’re handling your books on your own, allow your accountant to have access to all your software after you close them, suggests Logan Allec, CPA and founder of Money Done Right. “This will eliminate a lot of back-and-forth questioning that will arise if you simply send him an Excel sheet of your annual profit and loss, statement balance sheet and trial balance.”

Signs of a good accountant includes making sure they report everything correctly on your tax return. Oftentimes this means digging into the details and the supporting documents found in your bookkeeping software.

Have Proof of Your Estimated Tax Payments

Take screenshots of payment confirmations for all estimated tax payments made during the year and send them to your accountant, along with your other tax documents, recommends Allec. “As a CPA, I want proof that my clients actually made the estimated tax payments during the year that I told them to make before reporting them on the tax return,” says Allen.

Prepare 1099 Forms for Contractors

If you hired independent contractors in the past year, you’ll want to get your 1099 forms prepared. Per the IRS, if you’ve paid a freelancer at least $600 in 2019, you’ll need to file a 1099 for each person. Forms need to go to both the IRS and to your independent contractors. The deadline to submit these 1099 forms by January 31, 2020.

Organize Those Receipts

The ideal scenario is that you have all your receipts from business-related expenses stacked neatly in a safety box. The actual scenario? You most likely have piles of receipts scattered in random places — wedged in your car, at the bottom of your laptop bag or in a messy drawer.

While your accountant can most likely pull from your credit card or bank transactions, you’ll want to keep those receipts organized and handy. Besides providing proof of purchase, you might need them in the rare case that your business is subject to an audit.

Notify Vendors and Clients If You’ve Moved

If you’ve changed addresses in the last year, make sure you’ve notified all your clients of this change before the end of the year. Otherwise, you might get tax documents (i.e., 1099s) sent to the wrong address. You can also check your earnings from what’s called a Wage and Income Transcript. The transcript shows all the information the IRS gets from both your 1099 and W-9 forms.

Have Your Accountant Take a Look at Your Payroll

If your business has W-2 employees and you are handling payroll through a payroll platform, it might be a good idea to have your accountant take a second look, recommends Allec. “One common mistake is S Corporation employees who own 2% or more of the S Corporation not reporting on their W-2 health insurance premiums paid by the S Corporation on their behalf.”

There might be other mistakes you’ve made as well, and an accountant can help sort it out.

Set Aside Time to Get It Done 

Dedicate a block of time to focus on getting your tax prep in order. Otherwise, you might find yourself with more loose ends to tie.

To stay organized and streamline your tax prep, keep this tax return checklist handy. If you would like help with your taxes, Incfile can help. Our team of tax experts can help you prep and file your annual tax returns.


Jackie Lam

Founder at Cheapsters
Jackie is the founder of Cheapsters, a website dedicated to helping freelancers. She is passionate and dedicated copywriter and personal finance writer with nearly 10 years experience in copyediting, proofing, copywriting, photo research and licensing, production coordination, and blogging. Her specialties include: personal finance for millennials, long-term finance goals, budgeting on a variable income, and small business finance.

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