I am pleading with you…do NOT hoarde decades worth of financial documents, illegible scribblings intended to log all your medical expenses, little calendars with your mileage to doctor appointments on them, paystubs, cancelled checks, benevolent gifts and other useless tax write offs.
As a daughter-in-law of someone who never throws things away…I implore you to look beyond yourself and realize that someday, one of your children or one of your children’s spouses will spend hours and hours going through all that crap and then pitching it!
I am now surrounded by boxes of papers ready for the Shred-It people who will charge me by the pound to obliterate any traces of personal information contained therein. They charge by the pound. I have at least 90 pounds of papers.
The IRS and Medicare are tricky. You can claim expenses, itemize deductions, under certain circumstances. Most people don’t fit those circumstances. So…stop with the obsessive record keeping.
Don’t go to funerals, give a donation to the memorial fund and then write on the pretty little service program you received the amount of your “charitable donation” and the date you used it as a tax write off. That’s just sick.
Don’t paperclip or rubber band all these things together. I have to remove each and every one of those before the shredder can eat the paper inside.
Don’t keep everything in it’s original envelope with little notes on the outside referring me to the date, hour, minute and second that you spent the money or claimed the deduction. It just makes the whole process of going through your stuff even more aggravating.
If you had spent half the time, money and energy on playing with your children and grandchildren or having fun with your wife that you did keeping, sorting, filing, documenting and storing all these papers….I can’t imagine how different it would be.
Divine Graffiti 
So You Say