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How to Make Tax Season Less Stressful for Small Businesses

March 20, 2023

Between gathering and organizing receipts and bank statements and worrying about filing deadlines and cash flow, tax season is an exhausting time of year for many small business owners. According to a recently released survey by small business accounting software company FreshBooks, 80% of American small business owners feel at least some stress at tax time and nearly 63% rate that stress at 3 or more on a scale of 5.

But there are smart and easy strategies you can embrace year-round to make the season less stressful. Tony Constantine, a partner in the tax department at Cleveland, Ohio, accounting firm Ciuni & Panichi offers seven tips to reduce tax-time stress even if you, like these survey respondents, would prefer to move a nest of angry bees than work on your taxes.

1. Keep track of tax deadlines.

Know when your tax filings are due and mark them on your calendar. For small businesses, “it’s more than just April 15 you have to keep track of,” Constantine said, though this year, the filing deadline for federal income tax returns is actually April 18. Knowing deadlines ahead of time avoids last-minute panic. For small business owners, these are some important dates to keep in mind: Jan. 31 was the deadline for issuing Form W-2s to employees and Form 1099s to contractors, March 15 was the deadline for corporate tax returns for corporations and S corporations and April 18 is when first-quarter estimated tax payments are due for the current year. These deadlines are important to remember because, as Constantine said: “If you miss one of those dates, there’s going to be some pretty big penalties.”

2. Separate your personal and business expenses.

When you’re running a small business, it can be difficult to keep your personal and business finances separate. Some owners, for instance, use the same bank account or credit card for both personal and business expenses, making it difficult to distinguish between the two. And things like personal computers can be used for both personal and business purposes, making it unclear whether they can be written off. The risk when you co-mingle business and personal expenses is losing legitimate tax deductions, and it can even jeopardize your status as a business before the IRS. If you’re not sure whether to count an expense as personal or professional, Constantine suggested switching perspectives: “I advise clients to think of themselves as the employer who has an employee submitting an expense report. If that employee is submitting an expense report for dinner with their spouse, you’re going to say: ‘I’m not paying for that.’ But if they’re submitting a receipt for a dinner with a potential client, then you’d say: ‘Yeah, I’ll pay for that.’”

3. Keep good records.

Keeping accurate records throughout the year will make it easier to file taxes. Having detailed documentation of your financial transactions from receipts to invoices to bank statements to pay records will make tax season less painful. One of the most stressful parts of the tax process for small business owners is scrounging through receipts and paperwork, trying to account for every last penny. Indeed, lack of accurate records is one of their biggest causes of stress, panic and expense. “Right before I got on the phone with you, I was working with someone who didn’t necessarily reconcile their bank account and now we’re trying to piece through a mess,” Constantine said. If you’re not organized, he said, you’re going to end up paying someone “gobs and gobs of dollars” to re-create your entire year, which is far from ideal. “If your bookkeeping is spot on throughout the year, that’s going to eliminate a lot of stress.”

4. Invest in accounting software.

Excel spreadsheets are great tools for managing your finances when you’re just starting your small business, but if you are doing a substantial number of transactions, invest in an accounting program like QuickBooks, Constantine said. “Once you have hundreds of spreadsheets, it’s hard to keep track of money moving in and out.” Accounting software reduces errors and inconsistencies in your financial records. It also provides detailed reports on your finances, which can help you identify trends and patterns, track expenses and make better financial decisions. But before using the software, consult with a bookkeeper or a training professional from the vendor. “You want to make sure you’re utilizing the software correctly and you’re getting the most out of it,” he said.

5. Plan ahead.

Start planning for tax season early. If the first time you start thinking about taxes is when they’re due, you’re already behind, Constantine said. Planning ahead helps you manage cash flow so you can set aside enough money to cover your tax bill and avoid financial strain. And when you set aside time to study your finances and accounts, it alleviates tax bill surprises. “By the time tax season comes around, you should already have known what the results were going to be,” Constantine said.

6. Keep up with tax law changes.

Tax laws shift constantly, so stay informed about changes that might affect your business. And as a small business owner, know what credits you are eligible for and which ones you’re not. “The big one you hear about right now, which can be very tricky, is the Employee Retention Credit,” Constantine said. “If you listen to the radio, you’ll hear four or five commercials from people chasing those dollars out there for a ‘small fee.’” Constantine urged small business owners to be cautious of such promises. “Some folks are going to get in trouble because the IRS is looking hard at this credit because it’s pretty lucrative,” he said. The ERC was designed to provide financial assistance to help employers impacted by the pandemic retain employees. If you’re unsure whether a tax credit applies to you, consult a professional, he said.

7. Consider hiring a tax advisor to prepare your taxes.

If you’re looking for peace of mind, one of the best investments you can make is to hire a tax professional. The tax code is complicated, and even small mistakes can result in large penalties and fines, Constantine said. Tax professionals can help you navigate complex rules and identify potential deductions, credits and other tax-saving strategies you might not have known about. And for busy small business owners who already have a lot of responsibilities, that help can be worth its weight in gold.

By Rebecca Meiser

Contributor, Commerce + Communities Today and Small Business Center

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