Something else to consider: On the bottom of my invoices, in the memo line (I use Quickbooks Pro too), I write “Late Payments are subject to a monthly late fee of 3%.” I have no way of knowing how much of a difference that has ever made, but on two occasions after the first “reminder” email I’ve had clients include the 3% in a late payment without my even mentioning it.

Oddly, a few months ago I was looking back over the past several years of business, feeling fortunate that I had never had a true ‘deadbeat client’. Sure, a few clients took 60 days to pay, including a couple Fortune 100 companies (whose accounts payable departments know they can get away with it — and they do pay eventually.) But until two months ago, I had never had a client actually ignore invoices and “late payment’ emails and then phone calls from my accountant.

This client hired me to illustrate a book…and after we finished, asked me to delay invoicing until after they added one more illustration. It took two months for them to finalize that last illustration…and then after I sent the invoice, promised immediate payment. Well, after waiting 100 days more, (and following steps much like those outlined above), I went to the next step: threatening collection with the aid of an attorney. I didn’t expect much of a response, since it was simply another email on top of several previously sent and ignored. Guess what? Full payment arrived within 24 hours, with a request to please consider working for them again. (Like Steve said above, I’ll be booked that week.)

As you mentioned, however, the time and energy spent dealing with the pursuit of that payment was considerable. It was time I wish I’d spent writing or drawing cartoons.