Contractor payments feel simple until 1099 season arrives and you’re piecing together twelve months of payments from memory. The fix is straightforward: collect a W-9 before the first payment, log every transaction as it happens, and keep a running total per contractor instead of reconstructing it all in January.
Build that habit once, and 1099 filing turns into a quick export of records you’ve already been keeping, not a scramble against a deadline.








