Catching up on months of late books: where to start

Books that have slipped three, six, or twelve months behind feel like an enormous problem because they're usually approached as one. Broken into the right order, a catch-up is a finite, mechanical project — not a mystery, and not a reason to keep putting it off another month.

Start with the bank, not the categorisation

The instinct is to start sorting every transaction into the right category. Don't — start by pulling every bank and card statement for the whole period and reconciling the accounts first. Until every account ties out to its statement, you don't actually know whether anything else you do is correct, so categorisation before reconciliation is often wasted effort.

Work backwards from the most recent month

It feels more natural to start at the oldest unreconciled month and work forward, but the most recent month is the one you need current fastest — it's what any decision you make this week will be based on. Close the most recent month first, then work backwards through the gap. You get a usable, current P&L almost immediately, with the historical clean-up running in parallel behind it.

• Reconcile every account across the full gap before categorising anything
• Close the most recent month first, so you have current numbers to work from immediately
• Work backwards through the remaining months in order
• Flag anything genuinely ambiguous rather than guessing — a short list of questions is faster to resolve than books that look done but aren't

Decide what "caught up" needs to mean

Catching up for your own decision-making is a lower bar than catching up for a lender, an investor, or a tax filing. Know which one you actually need before you start, so you're not redoing the same months to a higher standard halfway through.

If the gap feels too large to start, that's usually a sign to hand the reconciliation step to someone else rather than a sign the business is in worse shape than it looks — the two are rarely the same thing.