"How does it make you feel" is a question I ask when I can tell a client is on the edge of letting go of something, but needs to make peace with their decision. Sure, the majority of the things I come across when sorting papers are mundane work & financial documents, but a myriad of personal items also creep into my sessions as well. I once was helping a client with a basement home office. She found me in another room and said, "Kacy, I just found a bunch of old journals, many with notes from past relationships gone bad. Should I keep them?" I can give a fast answer for something like an old grocery receipt or catalog, but this wasn't something I could decide for her (though I always err on the side of throwing it out, whatever IT is!) She proceeded to make an argument for keeping them by saying they might serve as reminders of what not to do in future relationships. I simply asked her "How do they make you feel when you look at them?" Her answer came fast and with a look of relief: "Terrible! They've gotta go!"
On that same note, an old friend of mine recently called to let me know I'd be proud of her for doing the same thing - tossing her old journals. In her own words, she said "Im letting myself grow up. It doesn't mean it didn't happen." I knew I had to share that insight with my readers. She went on to say, "They're just records of pain!" Amen to that!
I'm not suggesting that all journals should go in the trash. Hardly. If they are records of good times and fond memories, then they deserve your space. If something makes you feel anything less than neutral when you look at it, it has no place in your life. By all means, if it is a "record of pain," let it go!