Think if there’s anything you’re ok to get rid of right away. Since you have a hard time letting go, start with the least emotional decision; bank paperwork, deposit slips etc. (see below). The feeling of having to get rid of things sometimes make people hold on more, so tell yourself it’s ok to keep some things.
QUICK EDIT + SORT
Create labels using post-it notes, index cards or even painters tape on the floor or along a wall for categories you know you have: recycle, shred, tax papers, legal documents, college, memorabilia, article to read, etc, Grab a pile and start sorting things into their respective categories. The idea is to get papers sorted quickly and get the papers you know you’re not keeping out of the way. This is not the time to read and think; just sort into manageable piles.
If you have a room or area in your home where you can leave everything half-sorted end of the day that would be great (most people cannot get this done in one sitting). If not, use labeled shopping bags, folders or boxes to keep piles together until you’re ready to get back to it.
Once the papers are sorted, do a more thorough edit one category at a time, starting with the smallest pile and/or the easiest to go thru. Deep reading at this point will get nothing done. Skim the page to see if the article, notebook, etc has any relevance at this point in your life:
There’s an infinite amount of information out there. Chances are the articles you’ve been saving for years are outdated or maybe the reason you haven’t read them is that you actually don’t need to. Magazines run the basic same articles over and over again so chances are there’s nothing amazing you’ve been keeping that hasn’t been or will be repeated again.
If you write it off on your taxes, keep them. Ask your CPA (or who over does your taxes) for a list of what you need to keep. See above image for more details. If you’re not writing them off, there’s really no reason to keep them.
If you need them, the question is have you done your taxes? If you don’t actually need them to file, sort them by year. Don’t bother sorting them any further since odds are you’ll probably not have to reference them again.
Keep insurance policies, legal documents (as mentioned above). As far as your notebooks from college, be realistic. How long has it been since you’ve graduated and have you ever looked back at them? For some professions, it’s fine to keep some things from college, but certainly not all.
DISCLAIMER: I am a residential organizer, not commercial, the following info is for individuals only, also I am not a qualified financial advisor, attorney or CPA. If you have any further questions about what you should keep consult your qualified financial advisor, attorney and/or CPA.