When digitizing became “a thing” in the early 1990’s, it was more for businesses. It wasn’t until around 2000 that individuals started using that technology. As a result, most of the paperwork saved by previous generations, most notably the Baby Boomer Generation, and those that came before, wound up in filing cabinets or bankers’ boxes and remain in attics and garages.
I did a little research and learned that a record number of Americans turned 65 in 2025, with approximately 11,400 people hitting this milestone every day. This means that over 4.1 million Americans will turn 65 this year. This trend is driven by the Baby Boomer Generation and is expected to continue through 2027. The “Silver Tsunami”, as they (or I should say we) are lovingly referred to, represents the largest surge of retirement-age Americans in history.
This demographic also happens to represent a large percentage of my business. They are the ones that are downsizing and moving into smaller quarters or moving to be closer to family or, unfortunately, passing away. They are also the ones that didn’t take advantage of digitizing years of paperwork and now experiencing paperwork overload. Not necessarily just their paperwork, but the papers/files they inherited from their parents who are no longer able to handle it on their own. They may even be the adult child or surviving spouse who now has taken over the bills and paperwork and are overwhelmed with it all.
It seems that the most tedious task, and the one nobody wanted to deal with, was and still is paperwork. However, when people are downsizing and/or moving for whatever reason, chances are they don’t want to take the decades of paperwork that they saved with them. They probably won’t have the room to store all of it either. So, this is a great opportunity to unload a lot of it.
Further, if someone has passed away, the paperwork needs to be gone through to make sure that those that need important documents (CPA, Probate Attorney, Trustee, Fiduciary, Beneficiary) are able to get it.
Enter, Organizing Concepts and Designs, aka OCD. As most of my friends, family and clients already know, I spent 30 years as a Paralegal before starting OCD. Paperwork is my jam. Yes…its tedious but I love it. Please forgive this shameless plug but, if I can help people get through the paperwork, why not? It’s what I do. It’s a win/win!
So, here’s some unsolicited advice: If you, your parents or grandparents have filing cabinets and bankers’ boxes full of paperwork/files in offices, homes, garages and/or attics either start going through them or let me at it. You don’t have to do it all at once but start chipping away at it. If you don’t, the time will come when you will have to deal with it and, I can promise you, that’s not the time that you will have the bandwidth to do so.
Here are a few suggestions to get you started:
1. Talk to your CPA (but wait until after tax season as they’re swamped right now) and ask how long you should keep tax returns and the backup documentation. Some say 4 years, others say 7. I would defer to your tax professional.
a. Get rid of/shred the documentation for all prior years EXCEPT… hang on to all tax returns that you have until you file for Social Security as you might need them to prove your benefits.
b. Put them all in one box labeled properly so that they’re all in one place
2. If you or your parents sold a house/condo/townhouse/co-op or other residential property, keep any and all documents for 3 years after it was sold. Then you can shred those documents.
3. Keep any and all Wills and/or Trusts until the assets of the Trust have been distributed. If you are not sure, contact your Estate Planning Attorney for instructions.
4. Toss files/papers that are no longer needed and have no sentimental or financial importance (recipes, newspapers/clippings, coupons, travel itineraries)
5. Shred solicitations or anything that has a QR Code or invitation number
a. Note: You do not have to shred paper that just has your name and address as that is public knowledge
6. Shred anything with a full account number on it that isn’t needed for taxes. If it only has the last 4 digits there is no need to shred it.
7. Ask heirs and/or family members if they want the memorabilia before shredding (genealogy records, photos, personal cards/notes/letters, old report cards)
8. Toss all old/outdated appliance manuals
9. Shred all outdated/expired Insurance policies
10. Any and all non-tax related receipts
The list goes on but this is a great place to start.