Took me 5 months to realize my invoicing template was the whole problem
Back in January I finally admitted my books were a mess and hired a part time bookkeeper for $400 a month. She looked at my setup for about 10 minutes and asked why every invoice had the client's project name buried in the notes section instead of the line item. Turns out I built that template myself 3 years ago and just kept copying it, so nobody could match payments to jobs and I was eating hours on follow up emails. We fixed the template in one afternoon and my late payments dropped by half the next month. It stings that a $15 an hour fix sat right in front of me for 5 months. What's the dumbest thing you've paid someone to catch for you?