What do I do with my old bills/insurance statements/etc? I have executive dysfunction and I just can't find a simple method that works for me. It all ends up in a pile and every few months I pitch the whole thing and promise myself to do better next time. Perhaps there's an app, website, or program I should just digitize them into?
You're super likely to not need them yourself, the companies you've dealt with will likely have their records digitized for the 7 required years (or more)
Keep them for 1-6 months to make sure no funny business happens (I've caught my ISP pulling bullshit and proved it with my last 6 bills kept) and then shred them and you'll be fine
Oh, and try to get anything you can sent to an email with privacy, then they come digitized and can be kept forever with no real effort
I was in the same boat and wound up buying a scanner and installing Paperless. Scanner sends the files to my network drop box, Paperless picks them up from the drop box and digitizes them. I finally got rid of like an entire garbage bag of old pay stubs and stuff that I had been hoarding.
I have a filing cabinet with one drawer for hanging folders. Everything gets sorted and put in there. When a folder gets too fluffy I will pull it out and shred old stuff.
I could probably get rid of a lot but this method does come in handy occasionally. Most recently were my 2023 taxes which I filed in July (I had an extension). I yanked the 2023 file and immediately had 90% of my donations and medical expenses.