Reconcile the bank accounts first. Everything else in a cleanup depends on knowing what actually moved.
Being behind is more common than anyone admits publicly. We have taken on books more than three years out of date. The work is tractable — but only if it is done in the right order, because doing it in the wrong order means paying to categorize transactions twice.
Reconcile before you categorize
The instinct is to open the transaction list and start assigning categories. Do not. Reconcile each bank and card account to the statements first.
Until accounts are reconciled you do not know whether the transaction list is complete, and categorizing an incomplete list means redoing it when the missing months surface.
Fix the chart of accounts before the volume work
A neglected file usually has forty accounts where twelve would do, half of them created accidentally by a bank feed. Collapse them before you categorize a year of transactions into them.
Then work backwards, not forwards
Start with the most recent closed month and work back. Two reasons:
- Recent months matter most — they drive this year's filing and your current pricing
- Memory fades, and you are the only one who can identify an ambiguous 2024 charge
Know what you are buying
A cleanup should be quoted as a fixed-scope project before any work starts. The variables are the number of months, the number of accounts, and whether payroll is involved. If someone quotes a cleanup hourly without looking at your accounts first, get a second quote.
Once you are current, the maintenance question becomes what to pay yourself.