For most small service businesses, catching up on a full year of bookkeeping takes somewhere between two and six weeks of active work. A straightforward operation with one bank account and one credit card might be done in under two weeks. A busy contractor running multiple accounts with dozens of subcontractor payments and no existing records could take six weeks or longer.

Transaction volume is the biggest factor. A cleaning company processing 80 transactions a month is a very different project than a general contractor with 400 monthly transactions across several bank accounts and credit cards. More transactions means more categorization, more reconciliation, and more time chasing down entries that don’t make sense.

The state of your records matters just as much. If you have bank and credit card statements available through online banking, the data pull is fast. If you have receipts organized in folders or an app, even better. But if everything is in a shoebox or scattered across your truck and your kitchen counter, expect the process to take longer because sorting and matching documentation adds real time to the project.

Whether any bookkeeping was partially done also changes things. Sometimes business owners started the year in QuickBooks, kept up for three or four months, then fell behind. That’s a different starting point than twelve months of nothing. Partial books can actually be trickier if transactions were miscategorized or duplicated, because cleanup takes longer than starting fresh.

Subcontractor and employee activity adds complexity too. If you paid a dozen subs throughout the year, those payments need to be identified and tracked so 1099s can be issued correctly. Payroll transactions need to be reconciled against payroll reports. These aren’t difficult tasks but they take time to get right.

The process itself typically follows a pattern. Bank and credit card feeds get connected or statements get imported. Transactions are categorized one month at a time. Each account gets reconciled to its statement. Then the books get reviewed for accuracy and completeness. Catch-up bookkeeping isn’t complicated work, but it requires patience and attention to detail.

One thing worth knowing is that the calendar timeline and the active work timeline are different. A project that takes 20 hours of bookkeeping work might span three to four weeks because of back-and-forth questions. Your bookkeeper will need clarification on certain transactions. “What was this $3,200 payment to John’s Trucking?” Those questions pop up and your response time affects how quickly the project wraps up.

If you’re behind and tax deadlines are approaching, don’t wait. The longer you delay, the harder it gets to remember what transactions were for and the more likely you are to miss deductions. Most contractor bookkeeping services can prioritize catch-up work when there’s a filing deadline involved. Getting started is the hardest part. Once the work begins, it moves faster than most business owners expect.