Questions Seniors Ask About Organizing Paperwork

Paperwork is probably your biggest organizing challenge. It is for people of any age, not just seniors. As you travel through life, you pick up more assets, properties, bank accounts, medical care, and boring stuff like that. Sooner or later, you’re going to find yourself looking at a pile of papers. The questions seniors ask about organizing paperwork are good ones for all of us.

I promised you some short, snappy articles this month, so I’m breaking this into a Part 1 today and Part 2 to follow. Questions about paperwork? Hit me up in the comments.

Man, I wish I could make this topic more fun for everyone. I try my best, but today you might have to be satisfied with a pretty graphic.

Questions Seniors Ask About Organizing Paperwork


Questions Seniors Ask About Organizing Paperwork, part 1


How long should I keep old insurance statement and policies?

Home Insurance

If you already paid the premium, the policy period is expired, and you don’t have any outstanding claims, then old household insurance papers have no value. You can shred them after the policy period ends and you have the new policy in hand. The same goes for umbrella insurance policies.

Auto Insurance

Your auto insurance policy is only good while it is in force. As soon as you receive your new policy, you can remove the old one, shred the first couple of pages with personal information, and recycle the boilerplate pages. (You used to have to keep proof that you had a policy in the past, but those days are long gone since the insurance industry went to electronic records.)

Medical Insurance

You should keep medical statements until all bills are paid by you or the insurance company. Somewhat often, we use these bills to find and track billing errors for our clients. Very rarely, old bills have surfaced, and having proof of payment or account settlement can be helpful. This usually happens within a matter of years, usually with five years. Unfortunately, medical billing is less predictable than other types of accounts. If you have a chronic condition or an expensive procedure, file those records with your taxes during the year you were billed so the papers don’t become a mess on your desk. Sorry to say, but because our healthcare system is such a train wreck in the US, you are better off keeping medical paperwork rather than tossing it right away.

Life Insurance

Keep the last life insurance statement to prove payment while the policy is in force. Keep life insurance policies until the policy is discontinued or paid out. If you set up a file system, use a “remove and replace” approach with the last paid bill, you shouldn’t have much paperwork build up for this important asset. Having too much clutter in your paperwork could prevent you (or your loved ones) from finding this important asset when the time comes to cash in.

Business Insurance

Keep those old business insurance policies with your old tax returns. If a claim arises for a previous period, you’ll have the proof you need to protect your assets.


What medical papers should I keep, and for how long?

Medical papers aren’t just one thing…they are several things. There are a few different types of medical papers, and you need to know the difference:

  • Bills and receipts- pay and file right away. If you have a complex or chronic medical history, you may want to keep these with your taxes during the year they were billed. For routine bills, like annual physicals and dental checkups, you can pay and shred.
  • EOBs (Explanation of Benefits) from your insurer and Medicare. (Medicare is the government insurance company.) These EOBS are not useful, in almost every case, and they are not something that you should file and store more more than two years. As best I can tell, EOBs are created to torture us and to prove that bureaucrats are killing their quota of trees. If you have a complex medical history, you may choose to file them, but most of us can toss these asap, or within a year if you feel better filing and hanging onto them for a bit.
  • Insurance policies or copies of your employer’s benefits package. This may be printed or, more commonly these days, electronic. (see above)
  • Test results, prescriptions and script histories, eye prescriptions, immunization records, and other personal records that become part of your PHR, or personal health record. There is no single place these records live outside of the files you keep yourself. They exist across doctor’s offices and hospitals, so you may want to keep copies of important health records in your own files.
  • Articles on health and wellness might be interesting or even relevant to you, but are not, strictly speaking, part of your health record. If you can find it on Google, you probably don’t need to file it at home.

Click here for an in-depth yet simple way to organize your medical paperwork. 

How to organize medical records-file box


What other files should I have?

It’s only useful if you can find it. Here I tell you about the three files that most households need but may not have.

If you hate paperwork and financial matters, you probably have some letters about class action lawsuits in your clutter. Here’s the skinny on what those class action lawsuits are, and whether you need to keep the paperwork.

Keeping your files as simple as possible can be the key to eliminating your paper clutter. Overthinking will sink you. Consider a system that is waaaay more simple than you have now…

What if you hate to file? Then don’t! But do separate your papers at least by year. Toss all of your paper into a box throughout the year. At the end of the year, close the box, write the year’s date on it, and stow it for 10 years. (This is more than you really need for tax purposes, but 10 is a nice, easy number to work with.) Each year, throw out or shred the oldest box (which will be 11 years old). Is this the best way to file? Nope. But short of lighting a match, it is the easiest, and you’ll have whatever you might need, just in case.

Just remember what I said about adulting.

Questions Caregivers Ask About Organizing Paperwork

AARP gets these questions all the time. Here’s a good article to help you organize someone else’s paperwork if you are the caregiver.

Bottom line, always ask your financial advisor or tax advisor what you should be keeping, and take into account any unique situations in your household. But having a question about organizing paperwork isn’t license to keep all the paperwork. 🙂

I think that’s quite enough for today, don’t you? Come back tomorrow and I answer the questions about financial paperwork in: Questions Seniors Ask About Organizing Paperwork, Part 2.

Questions Seniors Ask About Organizing Paperwork Part 2



This Post Has 4 Comments

  1. Antoinette Rosati-Hanley

    Great e-mail I made a copy and sending it to my better half

    1. Darla

      Glad I can help. I hope your better half appreciates it.

  2. Linda Jean

    My biggest ongoing problem is the physical location of the files. I have a 2 drawer credenza with files in it but the drawers are deep and I can’t easily see or access what’s in them, especially in the back. I need my files more on surfaces so I can drop papers in as they come into the house, but I lack surface area and I don’t know how to make everything look visual pleasing if things will be in the open.

    1. Darla

      Making your file storage work for you is half the battle. If it’s too full, hard to reach, or poorly lit, you won’t use it. Period. You might be able to make room in your existing cabinet by getting rid of old, unneeded papers, and then use the top drawer for current files. Some of your papers that need to be accessed more often can be displayed attractively on a counter or desk. If you need help to make this work, please consider reaching out for a Zoom or in-person appointment. I’m here to help.

Comments are closed.