How to Catch Up If You’ve Fallen Behind on Bookkeeping

Kim Bernstein
May 16
3 min read

So... you’re behind on bookkeeping. Maybe by a few weeks. Maybe by a few months (or more—we’re not judging). The good news? You’re not alone, and it’s absolutely fixable.

Here’s how to catch up on your bookkeeping and get back to clean, accurate, and stress-free financials.

Quick Check: How Far Behind Are You?

Before jumping in, get a sense of where you stand. Your catch-up strategy will depend on your level of backlog:

☐ Behind 1–2 months
☐ Behind 3–6 months
☐ Over 6 months
☐ Haven’t touched my books all year

The further behind you are, the more important it is to pace yourself and possibly bring in help (we’ll cover that later).

1. Stop Avoiding It

Avoidance leads to anxiety. The longer it piles up, the harder it feels to start. So take a deep breath, grab a coffee, and decide today is the day you start getting back on track.

Progress over perfection.

2. Gather All Financial Data First

Before you can catch up, you need to collect what you’re missing:

Bank and credit card statements (PDFs preferred)
Receipts (paper or digital)
Invoices and bills
Loan or financing statements
Payroll records (if applicable)

Pro tip: Create folders by month to keep everything organized as you go.

3. Go Month by Month

Trying to catch up all at once will overwhelm you. Instead, work month-by-month:

Start with the oldest month and move forward
Reconcile each account before moving on
Mark each month as "done" to track your progress

Little wins keep the momentum going.

4. Categorize Transactions Accurately

This is where it pays to slow down and do it right. Don’t just throw everything into "Miscellaneous."

Accurate categorization helps with:

Clear profit & loss reports
Year-end tax deductions
Strategic business decisions

Tip: Use categorization rules or bank feed matching in tools like QuickBooks Online to speed this up.

Common Catch-Up Mistakes to Avoid

Even with the best intentions, it's easy to make errors when you're rushing to catch up.

Watch out for these:

Guessing categories without documentation
Skipping reconciliation to save time
Forgetting to record cash transactions
Ignoring unpaid invoices or liabilities

5. Don’t Skip Reconciliation

Reconciling = comparing your books to your bank statements. It ensures:

No missing or duplicated transactions
Your balances match reality
You can actually trust your numbers

Do this for each month and each account.

6. Ask for Help If You Need It

If you’re overwhelmed, unsure, or just done with DIYing it—bring in a pro.

A good bookkeeper can:

Catch you up fast
Clean up past mistakes
Build a system to keep you current moving forward

Pro tip: Hiring help now may save you time, penalties, and stress later.

7. Set a Simple System Going Forward

The best way to stay caught up is to make it easy to maintain.

Set a weekly bookkeeping day
Automate what you can
Save receipts digitally
Reconcile monthly (no skipping!)

Bookkeeping is like laundry: a little each week > waiting for a mountain.

Helpful Tools to Make Catch-Up Easier

If you’re not already using accounting tools, now’s the time.

These can drastically reduce the time and stress of catching up:

QuickBooks Online – for categorization rules, reconciliation, and reporting
Dext / Hubdoc – to scan, store, and auto-post receipts
Gusto / ADP – for payroll data integration
Relay / Mercury – modern business banking with clean data feeds

Bonus: Don’t Miss Tax Deadlines

If you’re catching up close to year-end or tax season, make sure you’re aligned with IRS/state deadlines for filings and estimated payments. Clean books help you avoid penalties and support accurate, timely tax filings.

Final Thoughts

Falling behind happens—life gets busy. But you don’t have to stay behind. With a little structure and support, you can catch up, clean up, and move forward with clarity and confidence.

Need help getting caught up? KB2 Bookkeeping & Tax specializes in catch-up and cleanup bookkeeping. We’ll meet you where you are—no judgment, just support. Let’s clean the books and clear your mind.