Fort Myers Bookkeeping Cleanup Checklist For Catching Up Past Due Months

Behind on bookkeeping can feel like walking into your office and seeing a stack of mail you've avoided for weeks. It's not laziness, it's load. In Fort Myers and across Lee County, seasonality, storms, and staffing changes can push admin work to the bottom fast.

This bookkeeping cleanup checklist is a practical way to catch up past-due months without getting stuck in the weeds. You'll start with a quick two-hour reset, then work month by month with clear priorities, time estimates, and a simple DIY vs outsource decision guide.

Quick note: This article is for general education, not tax or legal advice. Your facts can change the right approach.

If you jump straight into categorizing last summer's transactions, you'll burn time redoing work later. First, set the foundation so each month goes faster.

Hour 1: Gather and lock down inputs

• Collect bank and credit card statements (PDFs) for every missing month. If you can, download a full year at once.
• Confirm you have access to all accounts (bank logins, card portals, payment processors like Square or Stripe, and loan statements).
• Pick your catch-up window (for example, "August through January") and write it down. Scope creep is the enemy.

Hour 2: Create order and reduce future confusion

• Make one folder for each month (digital is fine), then add subfolders for bank, cards, sales, bills, and payroll.
• Export a transaction list from your bank and cards for the oldest missing month, then the next. This shows volume right away.
• List your "usual suspects" vendors and income sources. You'll reuse this list every month.
• Write down rules you'll follow, like "Owner draws never go to expenses" and "Sales tax collected is not income."

If your file is already messy (duplicate accounts, uncategorized transfers, feeds that disconnect), it may help to bring in QuickBooks assistance in Fort Myers before you invest hours in cleanup.

Think of cleanup like rewinding a movie. If you skip scenes, the plot won't make sense later. The cleanest approach is to complete one month at a time, in the same order, using the same steps.

1. Confirm the month's starting cash balances
   Make sure the bank and credit card opening balances match the statement ending balance from the prior month.
2. Import and match transactions (don't categorize yet)
   Pull in bank and card activity. Match downloads to any entries already in the books.
3. Reconcile bank accounts to the statement
   Reconciliation is your proof. If the bank doesn't reconcile, stop and fix it before moving on.
4. Reconcile credit cards to the statement
   Cards often hold the missing expenses that explain "where the money went."
5. Categorize income with support
   Tie deposits to invoices, sales reports, or processor summaries. For cash deposits, document what they were.
6. Categorize expenses and owner activity
   Separate owner draws, personal charges, and business expenses. Then classify the business items consistently.
7. Handle payroll entries and filings
   Post payroll totals, taxes, and any benefits. If something is missing, don't guess. Pull payroll reports first.
8. Review sales tax tracking (if it applies)
   If you collect sales tax, confirm it posts to a liability account, not income. Mixed invoices need extra care.
9. Run a quick reasonableness check
   Compare month-to-month sales, cost of goods, and key expenses. Spikes often point to mis-coding.
10. Save your backup for that month
    Keep statements and key reports together. The IRS focuses on support and consistency, not fancy formatting. Their overview of small business recordkeeping is a solid baseline.

Use this as a planning guide before you block your calendar.

The takeaway: reconciliation-heavy months move faster once your system is stable. If you're unsure what documents count as support, the IRS also spells out what records to keep and how your books should summarize transactions.

For business owners who want this handled end to end, Fort Myers small business bookkeeping services can turn a stressful backlog into a clean monthly routine.

Cleanup gets harder in Southwest Florida for a few common reasons. Seasonal revenue swings can hide errors. Contractor payments pile up. Then one bank feed breaks and the books drift for months.

Mixed spending is the biggest one. A few personal charges on the business card can snowball into hours of sorting.

Deposits that don't tie out come next. If you use a processor, one deposit can include multiple days, tips, refunds, and fees.

Old uncleared items are another red flag. Checks, ACH drafts, and transfers that never clear can throw off reconciliations.

This table helps you decide without guilt. Pick the path that protects your time and reduces risk.

Also consider retention. The IRS explains how long to keep records. Even if you outsource cleanup, you still want a simple storage habit.

If your goal is lender-ready financials (or you need tax filing support), solid books start with a clean general ledger. That's where financial statement preparation in Fort Myers fits after cleanup.

Catching up past-due months is doable when you follow a steady sequence: quick setup, reconcile first, then categorize and review. A good bookkeeping cleanup checklist keeps you moving, even when life and business get loud.

If you want help catching up and staying caught up, schedule a bookkeeping cleanup consultation with Meghan Sophia Tax & Accounting in Fort Myers. Bring your bank statements and your date range, then we'll map the fastest path to clean, reliable books.