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Are you the kind of business owner who just avoids doing your bookkeeping? It’s not something you enjoy, and it stresses you out. What if you do something wrong — and that mistake sends up a bat signal for the IRS to show up and audit you? So it feels safer not to do it at all.
It’s less stressful to not think about your bookkeeping than to struggle through it, right? It’s not close to tax time yet; you’ll figure it out when the deadline gets closer. Except by then it’s 87 times more stressful: you can’t find the documents your accountant is asking for, you’re not sure every expense is accounted for (you bought some business things from your personal account), and on top of it all, you have a tax bill and not enough cash to pay it. This guide walks you through how to catch up on your bookkeeping — calmly, step by step.
First: decide who’s doing the bookkeeping
You know you need to get things in order, but where do you begin? Start with one decision: are you going to do your own bookkeeping, or outsource it?
If you’re outsourcing, find the right person to do it for you. (Hint: this is something I can help with — book a quick chat and let’s see if working together is a good fit.) If you’re doing it yourself, keep reading and follow the steps below.
Step 1: Schedule uninterrupted time
Catching up can be stressful, especially when a whole year of bookkeeping is staring at you. Start by scheduling about two hours per week — a block where you can work without interruptions.
Make sure the kids are out of the house or looked after, the dog doesn’t need to go out, and your partner won’t come home and interrupt. Once you find (or create) that time, put it on your calendar as a non-negotiable recurring appointment you can’t wriggle out of.
Keep the deadline in view: your bookkeeping needs to be done before the tax filing deadline, which in the U.S. is usually April 15. The goal is to finish before that date, not on it.
Step 2: Gather all your documents
Next, gather everything you need. As an online business owner, most of your documents are probably already electronic — you just need easy access to them.
- Receipts: For anything you purchased during the year, get the receipt. If a business didn’t email one, log into your account portal — many recurring expenses store receipts there even when they don’t email them. If it’s not in the portal, email the vendor to ask for a copy. You need copies of all receipts for your bookkeeping anyway, so keep everything.
- Sales figures: Pull your totals from PayPal and Stripe if you use them, plus anywhere else you accept payments.
- Bank statements: Gather all of them.
Side note: If you use QuickBooks Online, sync your bank account and log in once a month — your transactions will already be waiting in QuickBooks, so all that’s left is to sort them and make any needed adjustments.
Step 3: Work through it month by month
Now that everything’s in one place, start entering it — and go chronologically. Begin with January and enter every transaction from your bank statement into your bookkeeping program.
For each expense, make sure you have the receipt. Either attach it directly to the expense in your software, or save it to your bookkeeping folder on your computer. I like to keep everything on my computer: a folder for each year, and inside it, each expense saved with a consistent naming convention — purchase date first, then the vendor name, then the invoice amount. That makes any receipt easy to find later when you (or someone else) has a question about a purchase. The easier your receipts are to find, the easier your bookkeeping is.
The most important rule: go in order. Don’t start with September, jump to March, then bounce to July. Start with January and work straight through the calendar — skipping around only gives you a headache.
You can get caught up — take it one day at a time
Just take it one step at a time. The more you stress about how much it stresses you out, the worse the whole process feels. If you truly can’t focus and get it done, that’s your signal to hire it out — and if you do, do it as soon as possible. Don’t wait until April to find someone to catch you up.
The sooner your bookkeeping is done, the sooner you’ll know what you owe in taxes, which means you can plan for the bill instead of panicking about it. Getting caught up isn’t just about compliance — it’s about trading that low-grade dread for a clear picture of your business.
This article is for general educational purposes only and may not reflect recent changes in federal or state law. It is not intended as legal, accounting, or tax advice. Always consult a qualified tax or accounting professional about your specific situation before taking action.