How to Catch Up on Bookkeeping When You’re Months Behind 

💡 Introduction 

If you’ve fallen behind on your bookkeeping, you’re not alone. Many small business owners — especially those running eCommerce stores, service businesses, or startups — get caught up in daily operations and push financial tracking to the side. 

Then tax season hits, or a loan application pops up, and panic sets in. Missing receipts, unreconciled transactions, and messy reports make it feel impossible to get caught up. 

The good news? Catching up on months (or even years) of bookkeeping is completely doable — especially when you have the right plan and support. 

At Remote Books, we specialize in helping small business owners across Canada and the U.S. clean up and organize their books quickly, accurately, and remotely — so you can finally feel in control of your finances again. 

Let’s walk through the five key steps to catch up on bookkeeping without the stress. 

1️⃣ Start by Gathering All Your Financial Records 

Before you can fix the books, you need to collect everything. That includes bank statements, credit card transactions, receipts, invoices, payroll records, and loan statements. 

If you’ve been using multiple payment platforms (like Shopify, PayPal, or Stripe), make sure you download all reports for the missing months. 

💬 Pro Tip: Start with your bank statements — they’re your source of truth for income and expenses. 

💡 How Remote Books Helps: 

We help clients securely connect their accounts through cloud-based software like QuickBooks Online or Xero. This lets us automatically import and categorize months of transactions in minutes — not hours. 

Instead of chasing paper records, you get an organized digital view of your finances from day one. 

Source: Canada Revenue Agency – Keeping Records 

2️⃣ Reconcile Your Bank Accounts 

Once you have your data, the next step is reconciling — matching what’s in your bookkeeping software with what’s in your bank and credit card statements. 

This step helps you catch missing entries, duplicates, or incorrect amounts. Without reconciliation, your profit and loss statement and balance sheet won’t be accurate. 

📉 Example: A missing $1,000 expense might make it look like your business earned more profit — which could mean paying more taxes than you should. 

💡 How Remote Books Helps: 

We perform bank reconciliation for every account, ensuring all data aligns perfectly. Our software flags discrepancies automatically, and our team investigates and fixes them. 

That means your books will reflect exactly what’s happening in your business — no guessing, no manual checking. 

Source: QuickBooks – How to Reconcile Accounts 

3️⃣ Categorize Transactions Correctly 

Misclassifying transactions (like putting software subscriptions under “office supplies”) leads to inaccurate reports and can cause tax problems later. 

Categorizing correctly helps you: 

• Understand true business performance 

• Claim all eligible tax deductions 

• Stay compliant with CRA or IRS rules 

💡 How Remote Books Helps: 

Our experienced bookkeepers use standardized charts of accounts tailored to your business type — whether you’re in eCommerce, consulting, or trades. 

We ensure every transaction is categorized correctly, following accounting best practices and tax guidelines in both Canada and the U.S. 

Source: IRS – Recordkeeping for Businesses 

4️⃣ Organize and Store Receipts Digitally 

One of the biggest struggles when catching up on bookkeeping is missing receipts. Both the CRA and IRS require supporting documents for business expenses, often for several years. 

If you can’t find receipts, try to: 

• Re-download them from vendors or email invoices. 

• Use bank and credit card statements to substantiate purchases. 

• Keep a digital copy going forward. 

💡 How Remote Books Helps: 

We use cloud document management systems that let you: 

• Snap a photo of any paper receipt 

• Forward invoice emails 

• Automatically match receipts to transactions 

This means your documentation is stored securely, searchable, and ready if the CRA or IRS ever asks for proof. 

Source: Canada Revenue Agency – Electronic Record Keeping 

5️⃣ Set Up a System to Stay Current 

Once you’re caught up, the most important step is staying caught up. 

 A consistent, automated system saves time and prevents future stress. 

💬 Smart habits include: 

• Reviewing your books monthly 

• Reconciling bank accounts regularly 

• Tracking receipts digitally 

• Backing up your records to the cloud 

💡 How Remote Books Helps: 

With Remote Books’ monthly bookkeeping service, you’ll never fall behind again. 

 We keep your records updated in real time, send monthly summaries, and prepare you for tax season early — so you can focus on growth, not spreadsheets. 

We also offer catch-up packages designed specifically for small business owners and eCommerce sellers who are months (or even years) behind. 

Source: Intuit QuickBooks – Monthly Bookkeeping Best Practices 

✅ Final Thoughts: You Don’t Have to Do It Alone 

Catching up on bookkeeping might seem overwhelming, but it’s easier — and faster — with professional help. 

At Remote Books, we make the process stress-free by: 

• Cleaning up months or years of overdue bookkeeping 

• Reconciling your accounts accurately 

• Organizing receipts digitally 

• Keeping your books up to date going forward 

Whether you’re a Shopify store owner, consultant, or small business operator, our remote, cloud-based system makes bookkeeping easy, transparent, and affordable. 

📞 Ready to get caught up? 

 Book a free consultation today and let Remote Books take bookkeeping off your plate — for good. 

References 

• Canada Revenue Agency — Keeping Records for Businesses 

• Canada Revenue Agency — Electronic Record Keeping (IC05-1) 

• IRS — Recordkeeping for Businesses 

• QuickBooks — How to Reconcile Bank Accounts 

• Intuit QuickBooks Blog — Monthly Bookkeeping Tasks for Small Business