It’s That Time of Year Again! A Roundup of U.S. Tax Season Advice

Got taxes on your mind? Here’s a roundup of our favorite tax season articles to help you get past that looming deadline stress-free.

tax season advice

The saying continues to ring true: Nothing is certain except death and taxes. So, despite the dread you might feel before the tax filing deadline, it’s got to be done—this year, next year, and the year after.

How can you make the tax filing season a little more bearable? All it takes is a little preparation and the right encouragement!

To ease your worries, here’s a roundup of all our tax season advice to help you get through that April funk.

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    Built for owners

    Ensure You’re Filing the Correct Tax Documents

    If you’ve ever filed income taxes before, you know that the process requires a lot of paperwork. But what kind of paperwork you file will depend on your business’s specific circumstances and situations. And suppose you want to avoid headaches like refiling your taxes (or, in certain cases, hefty fines). In that case, it’s essential to understand what documents you’ll need to submit with your taxes to ensure they’re filed correctly and in a timely manner.

    So, what might some of those tax-related documents be?

    Schedule C Form

    If you’re a sole proprietor or own a single-member limited liability company (LLC), you’ll need to fill out a Schedule C. (Read More)

    W9 Form

    Does your business work with non-employees (like independent contractors, freelancers, or consultants)? If so, you’ll need a W-9 form for each contractor you pay $600 or more in a tax year. (Read More)

    IRS 1099-NEC Form

    Using the information from your W-9 forms, you’ll need to file Form 1099-NEC for every non-employee, which reports those payments to the IRS. (Read More)

    Form 1099-NEC

    If you do a lot of freelance work and need help understanding how to file your 1099-NECs (Non-Employee Compensation), check out this guide. (Read More)

    Form 1099-K

    If you accept credit card payments or payments through a 3rd-party network, you’ll receive a Form 1099-K. (Read More)

    Tax Form 8829

    You must complete Form 8829 to claim your home office expenses if you run your business from home. (Read More)

    Form 8027

    If you own a business where tipping is the norm (like a restaurant or coffee shop)—and you have 10 or more employees on the floor on a standard day—you’ll need to report tip income using Form 8027. (Read More)

    Use Tax Credits and Write-Offs to Get More Money Back

    Paying taxes isn’t the most fun activity. But getting money back on your taxes? Significantly more enjoyable.

    But how you file your taxes will determine if and how much money you get back—and, more specifically, how you use tax credits and write-offs. Here’s what you need to know:

    How to Lower Self-Employment Taxes

    If you pay self-employment taxes, there are ways to lower the total you have to pay—like increasing your business expenses or claiming relevant tax deductions. (Read More)

    5 Money-Saving Tax Tips

    As a small business owner, you can deduct any business-related expenses you incur throughout the year—lowering your taxable income and potentially getting your money back instead of facing a tax bill. (Read More)

    2023 Small Business Tax Credits

    Depending on your business, you may qualify for small business credits, like the General Business Credit or the Small Employer Health Insurance Premiums, which offer even more tax savings. (Read More)

    Tax Write-Offs

    To use write-offs effectively, you need to know what qualifies as a deduction (like home office expenses) and what doesn’t (like entertainment). (Read More)

    Don’t Forget to Consider Your Business Structure

    Tax season advice 101: How you structure your business (for example, as a sole proprietorship, a partnership, an LLC, or an LLC taxed as an S Corp) can significantly impact how you file your taxes—and how much you’ll ultimately owe. Depending on your business and income, from a tax perspective, certain business structures may be more advantageous than others—and if you want to save money on taxes, it’s essential to understand them all.

    How Your Business Structure Affects Your Taxes

    As mentioned, how you structure your business will play a major role in how you pay taxes—and how much you’ll ultimately have to pay. (Read More)

    How to File Taxes for an LLC

    LLCs have a variety of structures (single-member LLCs, multi-member LLCs, LLCs that elect to be taxed as corporations)—and, as such, have various filing requirements. (Read More)

    10 Tips to Ensure a Smooth Tax Season From Home

    If you manage your business from home, you may be able to deduct some of your home-related expenses—like a portion of your housing costs and utilities—by claiming the home office deduction. (Read More)

    How to Claim Mileage on Taxes

    If your business requires travel, you can claim mileage deductions—65.5 cents per mile driven for business use. (Read More)

    accounting beyond the spreadsheets

    Work With an Accountant to Get Your Books in Order

    Few things are as valuable to small business owners as a reliable accountant.

    The right accountant can walk you through the entire tax preparation process, from ensuring your books are accurate and gathering the correct documentation to filing your business tax returns. But how, exactly, can you get the most out of working with an accountant during tax season?

    7 Questions to Ask Your Accountant at Tax Time

    Your experience working with a tax preparer on your business taxes will largely depend on the questions you ask—and knowing what questions to ask is a must to ensure your taxes are filed correctly. (Read More)

    How to Find a Good Tax Professional and Accountant

    Not all accountants are created equal. And if you want to hire a great tax professional? It’s important to know what to look for. (Read More)

    Add a Powerful Ally to Your Tax Time Toolbox

    If you want to file your taxes correctly and make the most of your available deductions and tax credits (and, let’s be honest, who doesn’t?), you need to have as many practical tools in your toolbox as possible—and that includes the right cloud accounting software.

    Cloud accounting software (like FreshBooks!) not only helps you prepare for tax season but also helps you better manage your business financials all year long. Let’s look at how FreshBooks can be your ally during tax season (as well as the rest of the year!).

    Why the Cloud Is Your Ally at Tax Time—and Beyond

    Cloud accounting can help you make sense of your financials and better prepare for tax preparation—freeing up your time and energy to focus on more important matters, like growing your business. (Read More)

    This Tax Season Find Your Strength in Numbers With FreshBooks

    FreshBooks can help you prepare for taxes with various helpful features—like tracking your income and costs, organizing and categorizing expenses, and tracking employee and contractor wages. (Read More)

    Tax Season Advice: How FreshBooks Can Help

    FreshBooks can help you keep your books organized, making filing your taxes more manageable and less stressful. Here’s what 6 business owners have to say about switching to FreshBooks. (Read More)

    Partners to Help You Prepare for Tax Season

    FreshBooks is an incredible tool to have in your tax tool belt. But if you want tax season to be as simple, straightforward, and stress-free as possible, you might consider adding a few more tools. (Read More)

    Graham Pugh Saves 44 Hours a Year on Tax Prep Using FreshBooks

    When we say FreshBooks can save you time on your taxes, we mean it. How much time? For entrepreneur Graham Pugh (self-proclaimed tax nerd), 44 hours—more than a full work week. (Read More)

    Be Prepared for the Worst-Case Scenario—A Tax Audit

    As a small business owner, getting auditing is probably at the top of your “do not want to experience” list. But audits do happen—and while you can take steps to prevent it, it’s important to be prepared should you ever find yourself dealing with a tax audit.

    Reasons You’re Still Waiting for Your Tax Refund

    If your tax refund is late, it could be that an audit is pending. Or, it could be several other reasons—like missing information or estimated payments posted to the wrong account. (Read More)

    How to File an Amended Federal Income Tax Return

    If you notice a mistake on your tax return (this year’s or a prior year’s tax return), you can avoid any hassles—like an audit!—by amending your federal income tax return via Form 1040x. (Read More)

    The Ultimate Guide for Tax Audits

    Don’t want to find yourself dealing with an audit? Avoid practices that can raise red flags with the IRS—like higher-than-average taxable income or out-of-proportion deductions. (Read More)

    Do These 5 Things to Pass a Tax Audit

    The chances you’ll find yourself dealing with a tax audit are slim. But if you do get audited, try not to stress too much! These steps can help you navigate the tax audit process—and come out unscathed on the other side. (Read More)

    financial jargon

    Stay on Top of Your Numbers All-Year Round

    The best tax season advice is to organize your finances year-round to ensure a smooth and stress-free season.

    Here are some tips to help you stay on top of your numbers throughout the year—so that when tax season rolls around, you are ready to roll:

    3 Reports You Can’t Live Without at Tax Time

    Staying on top of your accounting will ensure your financial reporting is accurate—and when tax season hits, having accurate financial reports (including your profit and loss and general ledger reports) is an absolute must. (Read More)

    Why You Should Track Your Business Expenses Daily

    Keeping track of your business expenses will ensure your accounting is accurate and help you maximize your deductions—so you save on your taxes. (Read More)

    Set Your Business Up for Success Next Year Now!

    Once your tax obligations are handled, it’s tempting to stop and take a breather. But the best time to prepare for next year’s taxes is when this year’s tax season wraps up. (Read More)

    7 Tax Terms Entrepreneurs Should Know

    Understanding tax terms (think withholding, adjusted gross income, tax credit eligibility rules, and itemized deductions versus the standard deduction) is key to ensuring your taxes are filed correctly—and if they’re not in your current repertoire, you’ll want to brush up ASAP. (Read More)

    Love Your General Ledger

    Your general ledger is more than a master document or accounting record. If you understand how to use it correctly, it can be your business’s most important reporting tool. (Read More)

    Track These Key Performance Indicators

    Key performance indicators (KPIs) are metrics that help you better understand the financial health of your business—and defining and tracking the right KPIs for you can help you make the best decisions for your business. (Read More)

    How Long Should You Keep Your Business Records?

    Understanding past financials can help you make better financial decisions in the future—which is why you’ll want to hang on to old business records, including tax returns and bank account statements, for longer than you think. (Read More)

    Make Estimated Tax Payments

    Want to avoid a hefty tax bill (and potentially penalties) when you file your federal tax return? You’ll need to make quarterly estimated tax payments. (Read More)

    Not Ready to File?

    Hopefully, this roundup of tax season advice has motivated you to submit your tax return well before the deadline. But if you find yourself scrambling to collect tax records and get your taxes filed, these last-minute tips can help. And if you aren’t ready to file on the tax deadline—don’t panic. You can always request a business tax extension. So long as you still make your tax payment on time—you won’t be on the hook for interest and fees.

    This post was updated in September 2023.

    Deanna deBara

    Written by Deanna deBara, Freelance Contributor

    Posted on February 8, 2023

    This article was verified by Janet Berry-Johnson, CPA and Freelance Contributor