How do you determine the difference between sentimental keepsake and items to give or throw away?

If it's "material" and can be replaced, I take that first into consideration.

Second I determine the sentimental value by weather or not anything else can rekindle these feelings in me. I think of emotions attached to physical items much like digital data from images stored on a memory card.

The images are sentimental and I don't want to lose it but I also don't have to keep it on the same memory card- I can transfer it digitally to another card.

Memories which are the root to the sentiment- can be transferred the same way but through a psychological process. The actual memory is not in the item but in your head- stored physically and chemically and associated to the item by your own design (desire + willing it into long term memory, triggered by associated physical external world properties).

When you limit your perspective that that memory or sentiment is only locked into that one item and you lose it (say it's lost, stolen, etc...) then you are a slave to that item in much the same way your a slave to the memory card an image you take with your camera is until you either make a backup copy physically (print it out) or move it to another card.

When you "know" the image is on another drive, computer, card, or anywhere else, the memory card the original is on can be lost and your not devastated!

We project our emotions onto items for whatever reason be it someone we love gave it to us, we like the item and attach the sentiment of the moment (use it as a trigger to re-experience that moment again) IN OUR BRAIN to it. It's merely an association but it's one that can imprison us to limitation of only being able to truly and fully experience it when we see THAT item.

If you use the concept that the actual memory is made, stored, and associated to that item in our own head- the item is just a catalyst or "shortcut" that eventually will not be necessary as through repetition of seeing it and rekindling that memory it's reinforced. Once that happens a SIMILAR item like it can also trigger the same pathways that light up the neurons that bring back that memory in full.

You know how they say you can't take it with you? They are talking about physically- but emotionally I believe we carry all those memories, experiences, etc... with us always- weather or not we access them is a different story. It's all in how you view the memory and it's trigger. You can create an internal trigger simply by thinking about the moment over and over (thus at first you keep the item to shortcut to this easily but after it's been reinforced enough times the item seems a bit "old"- that's because the memory is self sufficient at that point, you can simply "think" of the object as a mental shortcut not so much the physical one and rekindle the memory- your just transferring the shortcut into a mental switch instead. At that point I give the item away without losing anything- in fact it's fortified and re-associated by similar items I get.

Since we tend to choose things that have a reference to things we loved once upon a time (memories and objects memories) the sentiment lives on like a tiny soul reincarnating from one object to another but it's all still happening mentally. You "mentally digitize" it in the same way you'd transfer the words in a book into a PDF file and it evolves into more fluid movements and can even be duplicated!

Intuitively if your thinking about weather or not to get rid of something you know that getting rid of it is merely going to take away your crutch to that moment/memory- but that losing it won't affect the memory stored in your head and the associated feelings, emotions, etc... it provokes.

Although you receive an object from someone and attach sentimental value to it- realize that it alone cannot reproduce the entire memory (shortcut) as the brain stores things in fragments. Sound is stored in one part of the brain, images in another, and audio in yet another and so on.

Memories are actually networks of events based on our 5 senses. So if you take the object from where the sentiment originated (unless reinforced of course) you're actually removing many of the sensory memory associations that created that moment. This is why, for example, housewarming gifts keep value until you move to another house and change the environment and even mental source code of what gave it value (new home = excited state + getting gift = emotions layered over the excitement (simultaneous recording of sensory and emotional data). It's inherent value is based on your excitement level, it being attached to your new home, and a variety of other things.

When you move the item may still hold value but its real "power" is diminished and thus you can justify eventually getting rid of it. Now something like a wedding ring that surrounds and is worn all the time, is like a mental recording device as it is constantly seen in the light of everything you experience (good or bad) and in relation to the relationship itself (marriage/engagement/you and your partner)- so it's harder to justify parting with it and this is also likely the reason your told to never take it off- because it is a powerful and singularly important center piece of your relationship as just looking at it is like being able to rekindle EVERY memory you had.

It's easier to push a camel through the eye of a needle than for a rich man to get into heaven means to me that the more "wealth" also called appropriately- "Trappings of wealth", you have the more you value your stuff and thus cannot part with them easily as they become the very proof to you and others that you ARE wealthy- your net worth, but more importantly they become your prison cell eventually.

The irony is that with money you could easily get rid of things (sell them use the money to buy new things) and buy new ones but often put too much sentimental value on them for the reasons stated in this article- so they truly become "trappings". Many wealthy people are unhappy- ironically- but realistically those that can part with material possessions and realize that the real "gold" is in the awareness not the objects- that you never truly have to give up the sentiments (memories) even when you part with the objects- that you're free.

Think about it this way too- if your house burned down tonight- would you be devastated beyond just the loss of property and inconvenience?

Would you not be able to rebuild everything (providing all living people/creatures got out) eventually and return to the same status? Of course.

If I lost everything but my body, brain, and health (which is essential to maintaining your "hard drive" (brain) of the actual data you can't replace by the way)... I'd be inconvenienced, but the relationships I've forged will get me through it and if I helped enough people actively everyday people would be there to help me get through it, the stuff would be gone but my brain contains all the data still and I can re-associate it and build new triggers, and although it will not be easy or convenient I'd be ok and return to normal with new stuff.

True freedom is not financial wealth, its mental wealth- awareness, and the ability to let go of "earthly" possessions and put more faith and stock in my health to maintain my ability to manifest my emotional "base" again with new stuff.

I think of stuff a lot like emotional hard drives really- you store (by associating but really the object has no value other than your ability to easily shortcut to that info in your brain) emotions in them but your only making a copy from your brains memory card to a backup drive/object- in the end the object is just a convenience for emotion storage and whatever you use it for if it's a functional device.

I don't have this problem really...

As items are only owned (not owning me) until they are no longer useful or actively vibrant (affect me in positive ways vividly), once I tire of something often it's due to life evolution of thought and growth in all ways that change the very nature of the "stored" data's meaning- so being tired of something is likely your realizing that it's yesterdays newspaper- and there are more updated versions available so let it go (keep the memory though) and give it to someone who will value it more. It's also realizing that some objects may be entrapping you based on sentimental value that may no longer apply- or that you simply hold on to it because you feel guilty if you don't have it and the person who gave it to you finds out.

Money is just an obvious currency with parameters that are rigid, but ownership of items, earthly possessions is just as much a currency but it's more malleable and useful to use, not let it use us.

I proved this to myself when I had one item I just couldn't part with even though I never used it. An old car that was my first real and reliable car, a beautiful and unique car people kept wanting to buy from me. I parked it and didn't drive it for years- rationalized keeping it but one day realized it was affecting my ability to be happy- and literally gave it away. I felt a heavy weight lift- but did I lose the memory of the car? Nope I have images (detailed ones too) and looking at them or even thinking about the car brings me the same joy- Below is that gem I gave up- but I am not sorry I did.