Client Q&A: The Bookkeeping Questions We Hear Most This Time of Year
Q3 is where small bookkeeping problems start becoming year-end problems. These are the questions business owners are asking us most often right now — and the answers are usually simpler than the cleanup becomes if they wait until January.
"How far behind is 'too far behind' before I should just start over?"
There's rarely a point where starting over from scratch is genuinely the better option compared to a structured catch-up, even for books that are a full year or more behind. Starting over usually means losing the historical detail that a catch-up would have preserved — vendor history, category patterns, prior-year comparisons — for the sake of a clean slate that isn't actually necessary. A catch-up project, done methodically, almost always beats a restart.
"Do I really need to reconcile every account every month, or just the main one?"
Every account that moves money needs to be reconciled, not just the primary checking account. A secondary savings account or a merchant processor holding balance that goes unreconciled is exactly where errors tend to hide undetected for months, precisely because nobody's looking at it regularly.
"My P&L shows a profit, but my bank balance doesn't match. What's going on?"
This is one of the most common points of confusion for business owners, and it usually comes down to timing and accounting method. Profit on an accrual-basis P&L reflects income earned and expenses incurred, not cash actually received or paid — an invoice sent but not yet collected shows up as revenue, while a loan principal payment (which doesn't hit the P&L at all) still reduces your bank balance. The two numbers measure different things, and a mismatch between them isn't necessarily a sign of an error.
"Should I be worried about my 'Ask My Accountant' bucket getting big?"
A small number of genuinely ambiguous transactions parked there between conversations is normal. A bucket that's grown into a meaningful percentage of total transactions usually means categorization decisions are being deferred rather than made, and it's worth addressing before it becomes its own cleanup project.
"When should I start thinking about 1099s for my contractors?"
Now. Waiting until January to figure out which vendors need a 1099, and whether you have a current W-9 on file for each of them, is one of the most common last-minute scrambles we see every year — and it's entirely avoidable with a quick review in the fall.
As always, these are general answers to common patterns — if one of these sounds like your specific situation, it's worth walking through the details together rather than assuming the general answer covers it exactly.
Related service: IRS Resolution & Representation
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