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Why Bookkeeping is an Important First Step in Settling Your Tax Debt

When your business is in debt to the IRS, it can feel like you’ll never be able to resolve your back taxes. Where do you start? What if you can’t pay what you owe? What if you don’t have the financial records they’re requesting?

The good news is that there is always one concrete first step you can take: getting your bookkeeping up to date. No matter how much you owe in back taxes, handling your historical bookkeeping is critical to beginning the tax resolution process. Here’s why.

How does bookkeeping affect how much you owe in back taxes?

Here’s something many people don’t know: the IRS is very often wrong when they take a stab at guessing what your income and expenses are, which means that what you actually owe in taxes could be far less than what they estimate you owe.

Why? Let’s look at how the IRS figures out how much income you have.

If you’re a business owner who accepts credit and debit cards from your customers, your credit card processor is usually required to issue you a Form 1099-K. They’re also required to send one to the IRS.

Even for personal income that is not connected to your business (for example, interest that the bank pays you for money in your savings account, or investment income from selling stocks), the bank or financial institution will usually issue you a 1099 for this income as well. The IRS gets their copy of these, too.

What this means is that the IRS has a partial picture of your income, through these 1099s and other types of similar tax documents that are provided to them by third parties. The IRS then populates all this information on your Wage & Income Transcript, which you can access online.

Related reading: How Long Can You Go Without Filing Taxes?

That’s the income side of things. What about all the expenses that you pay to keep the doors open? There’s office rent, supplies, payroll, inventory, equipment, fuel, electricity, water, trash, computers, credit card processing fees, training for your employees, and the list goes on.

For most of these types of expenses (except payroll), the IRS has no way of knowing what they are until you report them on your tax return. And the only way to get these listed accurately on your tax return is by having solid, clean, updated bookkeeping.

Nigel’s nursery: an example of how bookkeeping can affect tax liability

Here’s an example of how this plays out in the real world.

Nigel owns a growing nursery and landscape supply store, and he has a team of 5 employees who help him run his store. He’s been in business for 9 years. During the first few years, Nigel was very particular about making sure he tracked all the money that came in the door, as well as all his expenses. His system was a simple Excel spreadsheet with two tabs: Income and Expenses.

At the end of the year, he would give his accountant the spreadsheet, who would then prepare the business tax return. The first three years in business, Nigel filed his tax returns and paid his taxes on time, like clockwork.

Things got busy. Nigel hired employees, and he started forgetting to update his tracking spreadsheet. Several months would go by before he’d remember to update it—but by then, Nigel couldn’t remember the details of all the customer payments he’d accepted, bank deposits he’d made, checks he had written, and other expenses.

By year 5, Nigel had stopped using the spreadsheet entirely. By this time, Nigel felt as though he’d never get caught up—and so he stopped filing tax returns too. In the back of his mind, he worried about the IRS contacting him.

Sure enough, Nigel started receiving CP59 Notices in the mail from the IRS, demanding that he file tax returns for the past 5 years. At this point, he felt panicked. He wondered how he could possibly find the information he needed to file those returns, given that he hadn’t updated his spreadsheet for such a long time.

In a flurry, Nigel decided to Google “business bookkeeping” and came across Bench. Relieved, he discovered that Bench specializes in doing the hard work necessary to compile financial statements for all 5 years, through historical bookkeeping. What’s more, Nigel also learned that Bench partners with tax accountants who specialize in resolving IRS tax problems.

Related reading: Tax Resolution: What You Need to Know

In the end, through leveraging the expertise of Bench and a specialized tax accountant, Nigel was able to not only get his delinquent tax returns filed, but now has ongoing, accurate and current numbers to look over every month. This helps him keep the IRS happy and make informed business decisions that maximize his profit.

There was another perk, too. Nigel ended up with about $50,000 in failure to pay penalties on the back taxes he ended up owing. Through working with an accountant who specializes in tax resolution, the entire $50,000 was removed through a penalty abatement. Needless to say, Nigel was very happy with the outcome. But none of this could have happened without updated bookkeeping.

How Bench can help

When you’re behind on your taxes, it’s difficult to know how to start catching up. But the first step, no matter how far behind you are or how much you think you owe, is always getting caught up on your books. Without updated books, it’s impossible to file an accurate tax return. Not only that, without your income and expenses tracked and categorized, you’ll be missing all the tax deductions and credits that your business is eligible for and that can significantly reduce your tax liability.

Bench’s Retro team specializes in getting your books up to date fast—even if you’re years behind. Our team also works with tax attorneys and tax resolution specialists, like Short Financial, who can help you navigate the entire process of settling your tax debt.

And once you’ve settled your tax obligations, Bench can continue to complete your monthly bookkeeping, so that out-of-date books become a thing of the past.

If you’ve been contacted by the IRS and don’t know what to do, you’re not alone. There is no tax problem that can’t be solved. Take the first step now and schedule a free consultation with Bench’s Retro team.

What's Bench?

We're an online bookkeeping service powered by real humans. Bench gives you a dedicated bookkeeper supported by a team of knowledgeable small business experts. We’re here to take the guesswork out of running your own business—for good. Your bookkeeping team imports bank statements, categorizes transactions, and prepares financial statements every month. Get started with a free month of bookkeeping.


This post is to be used for informational purposes only and does not constitute legal, business, or tax advice. Each person should consult his or her own attorney, business advisor, or tax advisor with respect to matters referenced in this post. Bench assumes no liability for actions taken in reliance upon the information contained herein.

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