I’d always respond, “The same as last month, $122.19. Due on the 19th of each month.”

He hung up and called back a few days later. “When did you say my payment was due?”

“The 19th.”

Click. The 19th would come and go. The insurance company would send a cancellation notice stating Tyler had until the 31st to pay the bill or he would be canceled. Ring. “Why didn’t you call me on the 19th to remind me my payment was due?” Tyler would ask.

“Because I have a thousand other customers, and I can't call everyone to remind them to pay their bill on time.”

“When is the last day I can pay my bill? I don’t have the money right now.”

“Like the notice you got says, you have until the 31st to pay the insurance. It will cancel at midnight on that date.”

“How much is it?”

“$122.19 plus a $10 late fee. So, $132.19.”

“Late fee? But it wasn’t my fault I was late. You should have called me.”

“Did you have the $122.19 on the 19th in your account?”

“No.” The 31st came and went. I got a call on the 3rd. “I’ve got the money now. Can I still pay?”

“Yes, but now that your policy is cancelled, they will charge you a $25 reinstatement fee. The total to reinstate is $157.19.”

“But my bill says it’s $122.19. I’ll have to put more money in the bank and call you later this afternoon.” He calls back on the 5th and pays his bill with all the fees. The policy was reinstated, and the company immediately sent a statement for $122.19 due on the 19th. The call cycle started all over again.

I finally had a heart-to-heart talk with Tyler. “I can’t keep doing this. Five phone calls a month about your bill? It’s not right. Imagine if all 1,000 of my customers called me that many times.”

He agreed.

I convinced him to switch to automatic payments, ensuring he had the money in his account by the 17th of each month so that they could draw it out early on the 19th. Yes, he’s had a few non-sufficient fund events over the years, and we dealt with them as they came along, but the five phone calls a month stopped.