Being retired (I’m in my eighth year of being retired, which was unfortunately forced on me) does a lot to dampen anyone’s motivation to do anything, really. Fortunately, I’m at a stage where nothing needs to be done right away.
In my case, the one major thing I have to do is the taxes. It doesn’t take a long time to do them anymore: I use the H&R Block tax program, which usually goes on sale in October or November. When I get the email that says the software is ready, I purchase it right away, because I get a discount for doing that. I’ll generally install it and activate it right away as well. That way, if there was anything that was a problem right away, I would know to hold off until there was an update.
Tax forms and documents usually start coming in starting the last week of the year. As they come in, I scan them into Evernote. That way, I know where everything is when it comes time to fill out the forms. I fill out the forms on the first Saturday in March, by which time I’ve received everything I need to do them. Of course, if I think there might be one or two documents I need that haven’t arrived, I might hold off until the second Saturday. The impoortant thing is that I have a date to give Mary when she asks "When are you going to do the taxes?"
I file both the Federal and State returns electronically. If I owe anything (and thanks to Obamacare I usually do), I wait until April 15 and charge it to a credit card, usually the Amazon Prime Card so I can get the points. As my father-in-law would say, you gotta work the angles…
So that’s my one major thing I have to do annually. Everything else (i.e. the bills) is done when it comes in. The utilities (gas, electric, water, garbage, phones, and Internet, and insurance) are drawn immediately from checking, while the credit card payments are scheduled when they come in for the date they’re due. It’s a system that allows me to spend as little time as possible doing them….