What makes tax season so stressful for most small business owners and freelancers? I think it can be chalked up to a few things. First, if you haven’t kept up with your bookkeeping, then you’re facing a year’s worth of accounting homework with a fast-approaching due date. If you don’t know how much you’ve made, you can’t know how much you’ll owe in taxes - you’re flying blind and that’s scary. And it gets compounded by a common fear among my creative friends and clients - the fear that someone from the IRS is going to knock on your door, tell you you’ve been doing everything wrong, and that you’re in major trouble.

For accountants, being stressed out during tax season is par for the course, especially if they have a big client list. But for small business owners, you don’t have to be drowning in a mountain of bank statements and receipts. You can hire professionals to help you that won’t make you feel like an idiot along the way. 

In this article, I'll walk you through what tax season is like when working with our bookkeeping agency, Hell Yeah, Bookkeeping. Let’s dig in.

If you fell behind on bookkeeping, we’ll catch you up

Whether you’re a few months or a few years behind on your bookkeeping, our job is to get you caught up so that you can get your taxes filed soon.  If you’re behind, you’re probably eager to get caught up quickly.

Here are a few factors that impact how fast we can get your accounting up to date:

• If you have a bookkeeping system set up

• How (and if) you’ve managed to keep your business and personal transactions separate

• Your business model

• The volume of transaction data

• Whether or not we need to input invoices

Tax time is less stressful

The joy of working with a bookkeeper throughout the year is that your bookkeeping is completed each month. You’re always up to date. It’s like when we were kids and had a few months to read a book and write reports... If you were diligent, you read a little bit over the few months (this was never me), when it was time to write the report, all you had to do was write the dang report. If you procrastinated, you were probably stressed by the pressure of writing the report, but also reading the book first! Imagine entering tax season with everything in order, imagine knowing where you and your business stand any of 365 days a year. That’s what bookkeepers do - they keep the books. 

We’ll give you and your accountant the reports you need to file your taxes

You don’t have to worry about preparing a business expense report from a 10-year old spreadsheet that only you can make sense of. If you get a 1099 late in the tax season, you don’t have to stress about making sure your accountant gets it because, with regular bookkeeping, we've already accounted for that income. Your financial reports are ready for your accountant well before the tax deadline. Without the mad dash, you have time to take a pro-active approach to filing your taxes. A typical reporting package includes an annual income statement, an annual balance sheet, a general ledger plus, and any notes we have for your accountant.

We communicate and work directly with your accountant

Don’t worry about playing an accounting-jargon-filled game of telephone between us, your bookkeepers, and your accountant. We’ll work directly with them to answer any questions about your accounting. We’ll also make sure to ask your accountant if there are things they’d like us to change or journal entries they’d like us to make to close your books out for the year. Our services are customized to each clients’ circumstances and business needs.

We make it hard for you to procrastinate

We do your bookkeeping every month so you have all the insights and data you need to run your business. Instead of worrying about keeping up or falling behind with your accounting, when we do the books, they become a beautiful place, full of insights and information about the work you do. They’re no longer a psychic drain or drag on your time and enthusiasm. Let us keep up with your books monthly. They will be a calm, sparkling, and orderly respite this stressful season—and all seasons.

And if this year, you’re facing another stressful tax season, I hope that you’ll decide it’ll be your last. Decide you’re done with the days of manually calculating business expenses in a spreadsheet, done with hours-long battles with QuickBooks tutorials, and YouTube accounting hacks. Pass the accounting torch. Let us help you.