The Guide to a Painless Tax Season

The Guide to a Painless Tax Season

Author: Bryce Warnes, Guest Blogger

Do the words “tax season” make you shudder? You’re not alone. Over half of US adults say tax season stresses them out. And when you run your own business, your tax time heebie-jeebies are bound to be even more severe. 

Tax season is faster and easier when your bookkeeping is organized. And our partners at Bench will handle all your small business bookkeeping, and even file your taxes for you.

But if you’re filing your own taxes, read on. We’ll cover all the forms you need to file and deadlines you need to meet—plus how to file on time or get an extension.

The documents you need to file taxes

When you file your tax return, you must be able to prove what you earned and what you spent —for the sake of reporting income, as well as claiming tax deductions. These records don’t get sent in with your return, but you’ll use them to calculate your total income and expenses for the year. And you need to have them on hand in the unlikely event you’re audited.

Expense report- Taxes

Basic info for filing small business taxes

  • Personal and business info: Your address, the address of your business, your full name, and your Social Security Number (SSN).
  • Last year’s filing: Having your previous return on hand makes it easier to complete this year’s return and keep track of info like depreciable expenses.
  • A tax ID number: There are a variety of different numbers you may use as a tax ID number—from your SSN to your employer identification number (EIN). Not sure which to use for your business? This article on tax ID numbers offers a handy rundown. 

Records Of Small Business Revenue

  • Invoices you sent to clients: Keeping copies of sent and paid invoices helps you track your revenue, and can support your case if your revenue or income are ever called into question by the IRS.
  • Records of goods sold: Cash receipts, or transaction lists from an online store or point of sale, can serve as a record of revenue you’ve earned.
  • Other sales records tracking revenue: It’s smart to hold on to any records of revenue you’ve got. In lieu of organized bookkeeping and regular income statements, you can use them to calculate your revenue for the year.

Record Of Expenses

By subtracting your expenses from your revenue, you get your total income for the year. That’s essential for filing. Also, many expenses are deductible—and if you make deduction claims, you’ll need to back them up.

Be sure to hold on to:

  • Rent receipts
  • Office supplies receipts
  • Employee salaries
  • Mileage records
  • Other deductible expense receipts

Annual Financial Statements

An income statement, balance sheet, and (if you use accrual accounting) cash flow statement for the year will make filing easy. Comprehensive financial statements give you all the info you need to file. If you don’t have financial statements for your business, now may be the time to hire a bookkeeper.

Essential Tax Forms and Deadlines

Tax forms

Once you’ve got your documents in order, get the forms you’ll need to file. The exact forms you’ll use, and the deadlines for filing, depend on your business structure.

Tax forms and deadlines for sole props

Filing Deadline: April 18, 2022 (the same as your personal taxes)

There’s no need to file a separate return for your business. Report your business income and expenses on Schedule C of your personal tax return. To claim itemized deductions, list them on Schedule A.

The IRS instructions will walk you through the process of tallying your expenses and revenue for the year, and determining your income.

Tax forms and deadlines for LLCs

Filing Deadline: April 18, 2022 (single member)
Filing Deadline: March 15, 2022 (multi-member)

If you’re a single-member LLC, you’ll file your taxes the same way you would as a sole prop. 

If you’re a multi-member LLC, you elect to file taxes as either a partnership or an S corporation.

Tax forms and deadlines for partnerships

The partnership files Form 1065, and each individual files a Schedule K1 to report what they’ve made and lost during the year. Partners claim unreimbursed business expenses on Schedule E.

Partnership filings, and Form 1065, can get pretty complex. For this reason, we recommend working with a tax professional to file your taxes.

Tax forms and deadlines for C corporations

Filing Deadline: April 18, 2022

In addition to your personal tax return, you’ll file one for your corporation using Form 1120. This form is similar to Schedule C of your personal tax return, but more complex—and separate from your personal finances. Most business owners hire an accountant to help with Form 1120

Tax forms and deadlines for S corporations

Filing Deadline: March 15, 2022

You’ll file a Form 1120S for your corporation, and each shareholder will need to report their profits and losses with Schedule K-1. Similarly to a C corporation return, most S corps get help from an accountant to file taxes.

Tax forms and deadlines for businesses that hire contractors

Filing Deadline: Sent to recipients by January 31, 2022

If you’re paid $600 or more to a contractor, you need to file Form 1099. Once copy of this form goes to the IRS, for the sake of filing your own taxes; another copy goes to the contractor, so they can use it to file their taxes. You need to file a separate Form 1099 for each contractor.

How to file taxes online

file taxes online

Gone are the days of paper filings. The most efficient (and popular) way to file taxes with the IRS is online. 

To file your taxes online, you have two options: Free File, or Free File Fillable Forms.

IRS Free File

The IRS has partnered with 13 providers who offer free versions of their accounting software that you can use to file your taxes online. You’re automatically enrolled in Free File once you sign up with one of these providers—you don’t sign up through the IRS website.

Most providers offer a basic software package for free. These typically aren’t able to cover all the needs of a business—such as filing itemized deductions. You’ll need a paid version for that; the packages recommended for sole props range from $54.95 ( to $94.99 (H&R Block).

IRS Free File Fillable Forms

Essentially, Free File Fillable Forms lets you complete IRS forms online, through the IRS website. These forms will do basic calculations for you, but they don’t check for errors.

If your business is small and relatively simple—like a sole prop—and you’re already experienced with filing taxes for your business, Fillable Forms may be a good choice. 

Fillable Forms will automatically calculate your tax refund, and you can elect to have it transferred directly to your bank account. You can also pay your taxes online.

Otherwise, the process could take a while, and you’ll run the risk of making errors. In that case, you may be better off having someone file your taxes for you.

Bench Tax

If you’re short on time and energy this tax season, and don’t want to wade into the depths of filing by yourself, consider Bench Tax. With Bench and Bench Tax, a team of professional bookkeepers will get your books caught up to the current month; then, they’ll work with tax experts to get your taxes filed accurately and on time—taking advantage of as many itemized deductions as possible.

How to get an extension


If it looks like you’ll be late filing taxes, file for an extension ASAP. It will save you from IRS late filing penalties, and getting an extension is pretty straightforward.

Filing a tax extension for your sole proprietorship or single-member LLC

If you plan to pay your taxes online, you can get a six-month extension through the IRS payment portal.
Otherwise, you can request an extension by filing IRS Form 4868.

Filing a tax extension for your multi-member LLC, partnership, or corporation

You can file for a six-month extension using IRS Form 7004.

File early, rest easy

If you can, file your taxes early—meaning, well before the deadline. This may take some prep, but it has advantages.

First, you’ll get your tax refund earlier. Remember, a tax refund is your money—you just happened to overpay it to the IRS, and they’re holding on to it. Your money isn’t collecting interest while the IRS holds it. The sooner you get it back, the sooner you can put it to work for your business.

Second, you’ll have the info you need to start planning your estimated taxes for the coming year—ticking one more item off your tax to-do list.

To file early, you’ll need tip-top books. The more organized your books, the easier it is to get the numbers you need to file your return. The best way to stay organized is to do your bookkeeping throughout the year, rather than handling it all in one mad scramble come January.

Ready to get your books in order? Check out Bench. They’ll do one month of bookkeeping for you, free.

Ready to get your books in order?

Tax time doesn’t have to be stressful. And it won’t be, so long as you have everything you need to approach it in an organized way. Your filing date, and the forms you need, vary according to your business structure—so make sure you know what’s what before the deadline comes.

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