I recently had an experience that shows no matter how careful we try to be when dealing with finances we still make mistakes every now and then. I have my finances generally automated so that I can spend as little time on them but I know that I still need to monitor my money.

I have my budget monitored in Mint and I also use a spreadsheet so that I can enter my receipts and have the most up to date information at hand. This has helped me to get a visual representation of my money and has also helped me a lot with saving money.

I am  currently paying my insurance through COBRA and have been mailing out paper checks through a friend of mine   while I was out of the country. I had reminders set up on a calendar and would notify this person every time I needed the check mailed out.

Except for one month when I forgot. The insurance check was NOT mailed in and and few days later my benefits were cut off. I did not find out until I logged in to my insurance account online one day and say that my account had been deactivated.

I was quite upset about this and found out after a few phone calls it was because the payment for a certain month had not been received. I went back through Mint and sure enough there had been a check cashed every month except for the last one.

It was completely MY fault because I was relying on someone who had their own life and schedule to take care of. I had slipped into the routine of the checks going out on time and just missed that one month where I forgot to remind my friend, so the check was not received by the due date.

I managed to negotiate with the insurance company to get my insurance benefits reinstated if they received the late payment PLUS the next month’s payment before the next due date. I told my friend to mail in the two checks at the same time and they were cashed a few days later. I also had to fax in a letter explaining what happened and requesting a reinstatement of benefits. It was approved and I am once again insured!!!!!!

I set up a new payment system through ING where the payments will not be late any more and added a second reminder in my calendar which will force me to check that the payment has been sent on two separate occasions. Hopefully my double reminders will ensure that my payments are never late again and automating through ING will take the pressure off me having to write checks and send them off in the mail.

I am feeling better now but this event has shown me the importance of continuing to monitor your finances even though you automate them. It has also shown me that I am responsible for my own money even if there is someone else involved in my financial transactions. My friend was really good about sending in my payments but we both had a lot going on and it was not my friend’s duty to make sure that the payment went out on time. We both thought it had been done but in the end it was up to me to double check that everything went as scheduled.