Get Organized for Tax Season- Tips from an Experienced CPA

Do you find tax season to be nerve-wracking? You’re not alone. Over half of US adults find tax season “stressful” or “very stressful.” While some of this stress may be due to tax payments, the majority of it relates to a lack of tax planning and organization. We’ve been through quite a few tax seasons here at Prestige Business Enterprises and wanted to share our top tips for getting organized for the 2023 US tax season, plus some free tax deduction downloads that you can use year after year.

Create Your Tax Form Checklist

One of the biggest headaches during tax season is the collection of all of your tax statements and forms. It would be pretty straightforward if you were just a W2 employee with no investments, properties, or children. However, most Americans have more things to account for like crypto gains and losses, Earned Income Tax Credits, HSA transactions, rental income, and charitable giving (just to name a few).

The best way to enter every tax season is with a checklist of all of the forms and statements you expect to receive from employers, banks, and government agencies. In 2023 those forms may include W2s, 1099s, K1s, 1099-Rs just to name a few.

You may also want to create a spreadsheet that you can use annually to track other specifics, like passive income sources, charitable giving, and mileage. We’ve got a few ideas on how to keep track of those in the next section, but for now, just make sure they’re on your list as numbers you’ll need to provide to your CPA.

Set Up a Digital Tax Folder

Perhaps you’re a tax traditionalist, collecting your receipts for the year in a binder or shoebox, only to sort through the crumpled stack of small papers at year-end. If that’s you, let us start by saying we’re glad that you have a place where you keep all of your tax documents together. That’s an important step in the tax organization process—one folder, binder, or shoebox for all your documents to stay together.

But let’s strive to make 2023 the year your tax documentation goes digital. Since the IRS accepts digital documentation as support in the case of an audit, and you’re expected to keep personal tax receipts for 3 years, going digital not only makes providing that support a breeze, it also saves you additional space in your office.

If you’re a small business owner, the QuickBooks app is one of the most popular ways to keep track of mileage, scan your restaurant receipts, and capture other miscellaneous expenses in one place. For your personal taxes, there are many apps out there nowadays to scan and store receipts for donations, home improvements, and other potential deductions.

The Stride and MileIQ apps are two options to track mileage while Expensify is helpful to track other itemized deductions. Just like tax returns themselves, tracking apps are not one-size-fits-all. Our recommendation is to try out several free apps and then pay for the one that seems to best meet your needs. Your tax preparer will (most likely) be relieved to receive your digital data when it’s tax preparation time.

Mark Your Tax Preparer’s Deadlines on Your Calendar

Most Americans have the April 15th tax deadline seared into their memories, but that doesn’t mean that you have until just before then to get your documentation in order. Tax preparation plans vary by office, which is why you will be on the “dream client” list if you reach out to your CPA first and mark your calendar with their important deadlines.

If you’re already on the documentation struggle bus, make sure your CPA is looped in early in case it makes sense to file for a tax extension. They may be able to support you with additional services to help get your books organized in a timely fashion for them to prepare and file your tax returns later in the year.

Even if you cannot accomplish it this year, make it a future goal to get organized early. Thanks to the IRS automatic extensions you are able to file an extension so that you have more time to organize and gather all your important documents.  An extension is not a red flag for the IRS.  Remember, though, that an extension is only an extension to file not an extension to pay, so if you owe monies to the IRS make sure you make a payment with your extension.

Block Out Time with Your CPA to Plan for the Next Year

While we’re happy to help our clients file their personal and business taxes each year, our real passion is to help our clients strategically grow their wealth to achieve their life goals. Planning time with your CPA for your financial health is another way to take care of yourself, just like going to a doctor for your physical health. Your tax advisor can provide important guidance on the complicated US tax code and any updates that may impact your life. Depending on your family structure, savings goals, and age there may be time-sensitive actions you should take before year-end to protect your income.

For example, if you are 73 years of age or older, you must take a required minimum distribution from each of your retirement accounts during the year or be forced to face a sizeable penalty. Rather than wait until year-end and risk forgetting or running out of time, we advise our clients to schedule their distributions for earlier in the year. You deserve to keep what you’ve earned and we’re here to show you how!

Employ a Knowledgeable CPA for a Smooth Tax Season

Perhaps you’re young and have simple tax needs. If that’s the case, using automated services like IRS’s Free File or return preparation via TurboTax and H&R Block could be the right option for you. But if your life and income situation are a bit more complicated, we strongly encourage you to employ a professional CPA for your tax needs.

Marriage, divorce, births, deaths, and major medical events all impact your taxes and how you file. If you’re dabbling in investing, particularly when it comes to things like cryptocurrency and real estate, there are important tax considerations when you buy, sell, and trade.  Owning a business also adds to the complication of a tax return.  Lastly, regardless of age, you should have retirement planning on your radar and may want to speak to your CPA about the best way to maximize your contribution while lowering your current tax liability.

Prestige Business Enterprises is Here to Help

Taxes are stressful, but our goal at Prestige Business Enterprises is to support our clients and empower them to make the most informed decisions when it comes to their annual tax planning. For more information on how we can help you get organized for the year ahead, email us at or set up a free consult here.

Let’s make 2023 the year that the shoeboxes in your home only contain really fabulous shoes!

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